What They Don’t Tell You About Getting Dressed in the Winter

Every winter I think to myself that finally, this is going to be the season I turn things around, that I figure out how to look chic through the winter. I am so hell-bent on figuring it out that I maintain zero qualms or hesitations about using the word “chic.” I flip through the lookbooks that land in my inbox and the runway photos that populate Vogue Runway and think to myself: Why did I give up last winter? There are so many great options out there! Just look at those silk pants, that trench coat — and what about that dress? This is it, Leandra. This is the season that we finally turn things around!

But it never sticks. I always forget until it’s freezing again that there is really no way around it. Dressing “well” in the winter (if, you know, you don’t work from home in satin kitten heels or a silk towel and you’re the kind of person who commutes to work by foot or public transport) is impossible. If this does not ring true for you, you must not live in a city like New York, which is a town remarkably distinct about its disdain for practical dressing. It has the ability to make you feel guilty for wearing snow boots!

Now that I am pregnant, the impossibility of dressing well through the winter is even more obvious because I have thus inoculated myself from the expectations of getting dressed at all. No, not dressed: ~DreSsEd!!!!!~ These days, I’m good for a pair of stretchy pants and a huge sweater, thick-ass socks and either a snow boot or sneakers and this — practical dressing — has really shone a light on all the things I never realized about the clothes I used to buy, but never really get to wear, for winter. Here is a comprehensive list of the myths that I used to believe.

1. Of course I will wear novelty tops. What else do I have going for me?

Here’s the problem: They don’t fit under coats. And particularly considering the trend wave we’re riding now, how the hell is a pair of sleeves bigger than two basketballs supposed to comfortably nestle themselves inside the armholes of a jacket. Can they? Should you expect them to? Don’t you worry about what will happen to the top if they’re smashed into a coat for too long?

2. Blazers are a tried and true form of layer that works.

Blazers obliterate my intentions once again: no matter how thin or thick, they just don’t fit inside winter coats. Sure, you can feign it, but it’s painful in that your mobility is severely compromised. You can barely bring your arm up to your face when you’re wearing a rigid layer under a coat. Also, I wonder, what’s the point of wearing a great blazer if no one, yourself included, can see it?

3. Winter is a great excuse to explore my style within the realm of midlength dresses and skirts.

There is a particular ratio ideally struck between a coat, whatever is covering your bottom half, and your shoes. Unfortunately, super long coats look awkward with midlength dresses or skirts if they’re not the same length, and where fabrics are concerned, the heaviness of your coat is disproportionate to the flimsiness of your skirt or dress. Short coats don’t keep your ass warm.

4. Silk is warm. I will wear a lot of silk.

Static, static, static. Have you ever tried to wear recreational non-pajama pajama pants with a sweater on a cold winter day? Follow up question if the answer is yes: Did all of the electric shocks incurred by the fabric combo light up your town?

5. I shall wear pumps with socks.

Camp socks? No. Flimsy socks? But will your foot stay in the pump?

6. I shall wear socks with sandals.

Cool in theory, but painful in action, particularly because the floors are always moist and your toes will get wet.

7. Winter is a compact time! I’ll wear flare and wide-legged pants that offer me additional height.

The truth is it’s a pain in the ass to get to wherever you are headed in fussy pants and heels and the floor is never dry. Your skin and lips and cuticles are — but the ground? Moist as can be, so the bottoms of those pants will get fuq’d. And you might slip.

8. This weather is a great excuse to wear cozy thick sweaters with all my favorite high-waist jeans!

So true in theory, but thick sweaters don’t tuck into high-waist jeans. They’re too thick. You can fake it, but it’s never the same as a tried and true, solid tuck.

9. I will wear many clutch bags.

What’s more elegant than a lady in a bell coat, holding her purse close to her heart? A reasonable question, but the answer is: avoiding hypothermia. You need your hands in your pockets lest you lose your fingers to the cold.

Homepage photo by Simon Chetrit; Feature photo by George Silk/The LIFE Picture Collection via Getty Images.

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  • BabyGotYak

    Thank you for bringing my inner monologue to life.

  • Ciccollina

    Urgh THANK YOU. Nothing is truer than the inability to tuck a chunky sweater. The truth is that winter is just about layer upon layer of unflattering synthetic fabric.

  • Adrianna

    Nobody told me to wear leggings underneath my jeans/pants, and I was so angry when I figured this out.

    • Leandra Medine

      i cant believe i missed this! you have to wear tights under all your pants and that makes fabrics that are not denim stick to you like you’re a fucking mousetrap

      • Elly

        Ugh, the times I’ve thought “can’t wait to wear this summer dress with tights and a cardigan in autumn!” and spent the roughly two hours a day I spend walking around tugging the damn thing out of my crotch as it wraps itself lovingly around my tights.

        • cristin

          that’s what slips are for! I have a whole wardrobe of mostly vintage slips of various colors and lengths, half and full slips, various colors and materials. They’re an extra layer of warmth plus they can be cute peeking out of your hemline. Also fleece lined black tights are skinnier and warmer than most leggings and I can wear mine under most of my pants and dresses. They definitely help as a layering piece with wide legged pants.

  • Sarah

    I’ve lived in New York for 5 years (i’m Australian) and I refuse to buy snow boots – you know the webbed ones. I complain and complain about how i can’t leave the house when it snows but SNOW BOOTS, i just can’t do. I don’t care how warm and comfortable Sorel’s are, they are an eyesore.

    • Adrianna

      But how do you preserve your shoes? I still cringe when I think about the pairs I ruined in the snow. I change shoes at my work desk on a regular basis. I finally bought a pair of Columbia snow boots to travel to the Arctic Circle, and I feel like a world of experiences opened up to me.

      • Millie Lammoreaux

        Bring them to the cobbler and have them weatherproofed. They put a coating on the leather to make your shoes far more durable. Also, always wipe off slush/salt immediately. I wear Frye motorcycle boots as my “winter beaters” and they’ve held up for years and years with this method.

        • Adrianna

          Oh, I’ve actually done this!

      • Sarah

        I wear Doc Martens with very thick socks or have a pair of chelsea boots i’ve had treated. I’m out and about for work all day so I can’t change shoes at my desk. I wish there were less bulky snow boots on the market

      • Rachel

        I’ve been wearing a great pair of Timberland winter boots for the last 4 years and I love them! They are black so the salt shows but they are easy to clean since they’re mostly leather/rubber. They are warm and fuzzy instead and most importantly waterproof! It’s hard to find a stylish winter boot and for a long time I gave up but these Timberlands are as close as they come. If they work for an Ottawa winter of constant snow and -30C then they’re pretty solid for any winter.

        • Adrianna

          I’ll keep Timberland in mind, it makes sense that that brand provides weatherproof options. NYC tends to be a giant puddle of slush and piles of snow at crosswalks after a snowstorm, so I’m fine with clunky winter boots. I’ll note that NYC = miles of walking every day, which is how the soles of a couple of weatherproofed boots still got ruined.

    • Millie Lammoreaux

      Yeah I’ve lived in New England for all of my 32 years, and as an adult I’ve never bothered with boots like that. A pair or durable ankle- of knee-high boots (the key is covering yr damn ankles!) with some socks is perfectly fine for day-to-day sidewalk strolls.

    • Mary

      Blundstones!! They’re not *the most* practical- mostly in the grip and warmth, but I had a pair that survived 3 Montreal winters of -20c, ice and snow. But the chisel toe black ones are nice looking, especially compared to Sorel’s and if you already have a somewhat rugged *look*.

  • Ah! I appreciate this so much because sometimes when I conceptualize an amazing outfit in my head yet can’t seem to execute it when the time comes, there feels like there’s something wrong with me. It’s my fault I can’t make this work, it’s my fault none of these outfits look good, it’s my fault I can’t meet my own expectations, etc. But sometimes the weather just DOESN’T PERMIT IT! & it’s not our fault, it’s just the way things work.

    The inability to tuck a chunky sweater into a pair of pants or a skirt is still disappointing, though. And I’ll continue trying to figure out a way to wear mini skirts in the winter while a) keeping my legs warm and b) not ruining the outfit with tights. Maybe one day we’ll win and find that sweet spot that seems so easy to conceptualize yet impossible to execute.

  • eva

    winter on the east coast made me feel like the little brother in “a christmas story” if you can’t bend your joints it’s an ensemble fail!

    • Leandra Medine

      and if you can bend your elbows, rest assured frost bite will kill you

  • NikNak

    HA I feel opposite! I feel so naked in the summer and never quite as put together. I love the layers and texture that comes with winter attire. I live in Seattle and the struggle to stay dry IS real though.

    • Totally agreed. I live in Syracuse, NY and it’s cold longer than it is warm, and my fall/winter wardrobe is so much better.

    • 808kate

      Portlander here. I feel the same!

  • Wollstonecrafting

    Why do winter coats have such slender arms? I could not agree more with this assessment.

    • Alexia

      Omg I agree!! Very frustrating

      • Helen

        Yes! So glad I’m not alone in the arm suffering!

    • Elly

      Oh my god yes. I find it impossible to find a winter coat, because I’m pretty built up top, broad shoulders plus big biceps, and if I get one in my size I basically can’t lift my arms. Plus I’m 5’4 so it’s this long list of calculations and details to look out for, to get a coat that’s oversized without being too big (to avoid the “boulder covered in a blanket” factor), with enough room in the arms.

    • Ai-Ch’ng GB

      When we were visiting Japan recently, we saw that many of the local coats had deep armholes and roomy sleeve. They looked like modern woollen kimono jackets. Very warm, very comfortable, and in that regard, very cool. I wanted to buy one, but couldn’t decide – there were so many beautiful ones! And I love the men’s versions, which are again, even roomier. Those jackets with cropped corduroy flares were so cute!

  • Ugh then there’s the inevitable mid-winter slump where everyone’s coat is cooler than yours because you’re so sick of looking at yours you want to light it on fire (despite the fact that you realllllly love it…you both just need a break).

    • Millie Lammoreaux

      DUDE, YEAH. Just ordered a new coat for this specific reason.

    • leilanigl

      I have an obnoxious and beautiful orange plaid double breasted coat that I’ll be breaking out tomorrow for exactly this reason. Every damn year this is when I bring it out. I can’t look at my parka any more.

      • Kiks

        My version is a robin’s egg blue wool/mohair super fuzzy and oversized double-breasted coat I found on clearance two springs ago. I feel like a Muppet in it. It’s fabulous.

        • That sounds incredible and now I need to find a muppety blue coat!

    • Cattja L´esh

      so true!

    • ladle

      See I am totally different. I will wear one coat for years if it’s my favourite. Until it rips. Then I switch.

  • Jessica

    I’ve given up on being creative about winter dressing and now wear the same thing most days for several months – slim or skinny jeans, ankle boots, thick turtle neck sweater (add hoop earrings to make your turtle neck look extra chic), long coat (bought one size bigger than I need to accommodate the aforementioned big sweater).

    • Jessica

      Also, I hate wearing gloves because they are the most annoying things in existence so I use a muff instead. They look super elegant, keep your hands extra warm and if you get one with a string for round your neck, you don’t have to worry about putting them down when you need to use your hands.

    • Amanda Faerber

      I want a muff now. Dammit.

    • Ai-Ch’ng GB

      Same like you, for all those cold months, especially with earrings (I have multiple ear piercings that I feel are like the only things I keep from summer, and can make me feel less like a snowman).

      Except that I rotate between four different (two sizes up and so what I wear throughout summer) bias-cut, silk, spaghetti-strap, midi-length slip-dresses, over a thermal woollen singlet (great for keeping my core temp consistent and minimising flu and achy back/kidneys), semi fitted short-sleeve/three-quarter sleeve cotton T (to keep my shoulders warm), and thermal black woollen leggings with thick socks, and leather high-top/low-top sneakers/leather flat ankle boots.

      Over all that, I wear a hooded thermal woollen long-line, zip-up hoodie (so I don’t always have to remember to bring a beanie, and which keeps me really warm when the hood is pulled up over the beanie), and a thick, quilted-lined leather motorcycle jacket that’s oversized, so it covers my backside completely.

      All my thermals are by Icebreaker (I don’t work for them), and they’ve changed my life – so lightweight, thin, super-warm. All the lightweight layers trap air, and are easily shed (and compact to stuff into tote bags/back-packs) when I walk into the humid and usually overly warm indoor-heated places.

  • Millie Lammoreaux

    Additional thoughts: I LOVE being a fat woman in the winter. My big ass and thighs provide endless insulation, and I’m never so cold that I have to resort to tights/leggings under pants, etc. Sorry for the brag, but I’m seizing the opportunity here.

    • Slow clap

    • Olivia Lauren Hawk Moore

      HAHA I had this exact experience two weeks ago in NYC with friends for holiday, where all of my dear rail thin comrades had on three layers each and I had to shed my inner most tshirt in the midst of shopping because I was really, truly sweating. and the one day I tried to layer leggings under my jeans I stripped those off as well. too hot. cant move. don’t need.

    • coffeebee

      I envy that and I believe you. I’m gangly and don’t have enough natural insulation to keep warm. Even with a thick sweater, Uniqlo puffer, and a down coat…my ass is shivering.

      • Alexia

        I wouldn’t say I’m extremely thin, but I’m definitely on the gangly side being quite tall, and I only survive the winter with very warm clothes and coats and the heating system jacked up!! I also have very cold hands and feet, an affliction I am told mostly affects tall, slender, white people so this must be part of our punishment for our historically horrible behavior and privilege.

    • TinySoprano

      One of my best friends proves this point by wearing short sleeved dresses well into autumn and going coat-less well into winter. And if you see her in her awesome 19th century coach driver coat with the super swoopy back seams you know it must be cold enough to freeze the balls off a brass monkey. That woman is made of iron.

      • Aww. ‘Same here. Your friend must be my virtual twin. A woman after my own heart!

    • Ciccollina

      Do it babe.

  • Jessica

    This couldn’t be more timely for me. I just moved from my hometown of LA to Portland, OR and while it is no where near as brutal as an east coast winter, coming from SoCal where the toughest spot we get is maybe like a 2 weeks total of rain a year and temps in the very low 50s, this has been an adjustment to say the least. I’ve been trying to make it a fun lil mission of mine to build my winter wardrobe. From what I can see from the seasoned PNW winter vets here, its all about the North Face and Columbia jackets in various colors and Sorels and/or Hunter Wellies…so I’ve simply come to the conclusion that its all in the outerwear and a few good pairs of boots (although ya girl needs a REAL boot. Theres no way for me to get these rubbery winter options to work). If I have a decent coat & boot/bootie option for any outfit and maybe a hat or scarf if i feel like dealing with the bulk, anything is possible. And tights! I’m all about a sheer black tight! Keeps the legs warm and has a little bit of sex appeal (opaque tights make me feel like a 3rd grader).

    • coffeebee

      *waves* Hi! I moved from Texas to Portland recently and it’s been a learning experience for me, too. It’s all gotta be warm AND waterproof. I think I’m finally getting it down, but it still seems like I rotate the same 4 outfits over and over again. I went into this winter knowing I was clueless and just want to stay warm. Something I tried this week was layering my summer linen tunics and sleeveless tops over a thin turtleneck – it was surprisingly warm.

      • Jessica S

        I’ve been thinking of doing the turtleneck layering thing too, specifically with a few silky slip dresses i have. Great minds! And yes, EVERYthing waterproof (because apparently in Portland umbrellas are for suckers. Go figure)…can’t believe how hard it is to find a raincoat that isn’t reminiscent of Paddington Bear.

  • Amanda Faerber

    I feel same about all of these. There are two weeks at the beginning of fall when I get really excited about the creative layering, etc. but right about this time of year, I start to hate and feel de-inspired (deflated and uninspired) by everything I own.

  • Leandra, you make me sad in the winter. You have an insane wardrobe. For the love of fashionable baby Jesus, layer up and challenge the rules you create for yourself. Here are my suggestions:

    1. Get a bigger coat. Ur man’s! A size bigger! If the balloon sleeve fits… !!!
    2. See #1. Seriously. Idk where you are getting your coats from but I bought a vintage wool coat from beacons closet earlier in the winter. I layer a long but thin boiled wool Eileen Fischer coat underneath and I ALWAYS fit at least three more layers under ALL that, one of which is usually a blazer. No excuses, lady!
    3. Saying a skirt needs to be the same length of your coat is a silly rule. Nobody cares! Own the look! Play with hemlines!
    4. Static happens.
    5 and 6. Give up the sandals and pumps, it’s just not worth it.
    7. Wide length pants are fun in theory but never worth it in the long run. Bell legs plus snow equals human Zamboni. You are better off wearing a skirt or dress.
    8. Fuck the tuck and get loose, it’s the perfect time to wear big chunky sweaters! Put a belt on it! (Maybe wait for when you’re not pregnant for that) but seriously. Oversized sweaters, weater dresses, whatever. Get on it.
    9. If clutch you must, buy a pair of gloves, damnit!

    • Jessica

      I would never consider tucking a big chunky sweater. How would you even go about that? Just wear an extra vest top underneath and tuck that in to keep your belly warm.

      • Me neither. It’s a fashion thing I just don’t get, like draping a coat over your shoulders.

    • coffeebee

      fuck the tuck!! yes.

    • Elly

      Fuck yes. For (3) I’d usually wear a skirt that’s longer than the coat but if that doesn’t happen, eh. And socks in sandals or pumps looks nice in fashion photos but I can’t imagine walking around that way, unless you’re in the situation where you might end up in a street style photo. And even then, wearing practical footwear would be a service to the rest of us.

      That said, (7) haha, but also if you get your wide-legged pants in 7/8 length you can avoid the human Zamboni factor in many situations. Though admittedly if there’s a foot of snow or more, that shit is probably going up your pant leg and down into your socks.

      I dunno though, my modus operandi for dressing in general is seeing how close I can get to wearing pajamas and still look businesslike and smart by deploying braided hairstyles, red lipstick and fancy earrings. With mods, it works in every season.

      • I don’t really like the air space between leg and fabric concerning wide leg pants, so I’m biased against them. I LOVE your method!! I’ve been meaning to get into styling my hair. I don’t do anything to it now, but you have inspired me!

        • Vintage Vixen

          Regarding ‘styling hair,’ I have waist-length ethnically-mixed hair. It is a challenge to stuff under hats and hoods and look presentable when I reach my destination. It’s also a challenge to keep it together when it snows or sleets. So years ago, I decided that I would skip “styling” it and consider winter a ‘rest’ period for my hair. I keep it in various protective styles (buns, braids, twists, chignons), skip heat, air dry, and indulge in my favorite oils (organ, coconut, etc). When spring arrives, my hair is in great condition, ready to be worn in long waves, free of hats and hoods and cold. My stylist dusts the split ends off and it’s good to go until the following December.

    • Keisha

      Socks with sandals…

    • Sarah

      I was thinking the same about #1. I’ve actually started buying coats that would normally be WAY too big on me, allowing me to layer a nice sweatershirt or pullover over whatever fashionable top I’m wearing that day. I’ve also started wearing sweatpants over tights on the metro (no shame) because I miss wearing dresses to work in the winter. I look like a mess on my commute, but at least I look cute the rest of the day.

      • HELL yeah. Wearing sweatpants on the subway is genius. It’s almost like bringing your comforter with you. I’ll do anything for the illusion of staying in bed on smack-your-face nasty, cold weather days.

  • Ugh I’m sorry, I love my California winters when the hardest decision is which one of my spring weight coats goes best with my flannel midi dress.

    The struggle is NOT real….

    • Jessica

      YES. I recently moved to CA and now enjoying being able to wear a nice elegant slim fit coat over my usual summer t shirts for winter-appropriate attire.

    • Miss Crystal

      Hahaha I have a ridiculous amount of spring “coats” for someone who has lived in SoCal her entire life. Winter here = dress + knee length coat or trench + tights/scarf for flair. I used to complain about it always being too hot to wear “cute wintery outfits”, but especially this winter, I feel like that’s kind of offensive to our east coast sisteren.

  • Lindsay D

    I wear uniqlo heat tech everything! the leggings in stead of tights with dress and camis and tees for layering without bulking.

    I also use the feet warmer things people use for skiing in my pumps during the winter, they add heat and your foot sticks to them.

  • Autumn

    That’s exactly why I never wear blazers in the winter. And why all my blazers look so sad right now.

  • DelphineGarnier82

    Winter is weird for me because I start feeling warm easily. It’s the same reason I hate the hottest of summer days. You know it’s REALLY cold if I leave the house in layers that go beyond wearing a coat over a sweater. With the usual winter weather I have to strike a balance of not getting cold outdoors but not dressing so warm I feel really suffocated indoors. I have to dress lighter than the average person in the cold.

  • Christine Dyson

    Heat tech from Uniqlo has been a game changer this winter, I’ve been able to wear non winter clothes without freezing to death or feeling totally bulky.

    • Bee

      Totally agree with you on this. I just got a pair of leggings and one of the long-sleeved shirts and they’re magic. Currently wearing the heat tech leggings underneath my workout leggings and I’m feeling good! Haha

  • Rachel

    I always find winter dressing challenging especially living in Ottawa where we frequently experience -30C weather and storms with 20cm of snow. I find myself wearing the same boring look constantly consisting of skinny jeans and a sweater or tshirt with a thick cardigan. I feel like I’ve finally managed to get over the winter dressing blues thanks to my new Club Monaco winter coat which is surprisingly warm, stylish and doesn’t break the bank. Just adding this piece to my wardrobe has made me feel so much better about what I’m wearing under the coat. (Also winter dressing pro tip: size up when it comes to winter coats so you can fit chunky sweaters under and layer while still being comfy.)

  • arthuranddaughters1

    I’m soooo surprised Leandra that you don’t enjoy winter dressing!! There are so many layering opportunities …quirky accessories and FUR!!! I do agree that pregnancy sucks the fun out of dressing. You are forced to wear what fits and not what you feel….

  • Kate

    oh my god this is the first year I stopped giving a good god damn about looking cute in the winter and this is the first year I’m warm. I walk to the train, smug as hell, knowing that girls with their BARE ANKLES OUT IN DECEMBER will repent one day. My, the years I suffered for fashion! 4 pants or bust!

  • Teresa


  • Marta Bosiak

    1st rule of winter: wool every-damn-thing!
    second rule: the layer closest to the body should be tight. skin tight.

  • francesca

    I was hoping for a post like this so much!

    Last August I moved to Toronto from Milan and I’ve been so depressed in the last 2 months because I’m always wearing the ugly combo of UGGs + Canada Goose parka and rotating the 3 pants I own that fit me with thermal leggings underneath.
    Also, is it that hard to design a pair of boots that can keep you warm AND are beautiful? I don’t mean acceptable or not super ugly, I mean BEAUTIFUL.

    It feels like an unresolvable enigma… at least I feel less alone now!

    • Cocktails_with_Clytemnestra

      Hi! If you’re in Toronto go to Uniqlo and get some HeatTech leggings and tops. They’re thin and super warm and will fit under pretty much any article of clothing. Or go to the Bay and pick up some silk thermal underwear. Silk works best in winter as a base layer. Club Monaco has gorgeous warm, woolly coats that are cut generously enough to wear a chunky sweater underneath. If you want to spend more, go to Max Mara – my coat is a camel hair wrap of theirs and I actually sweat in it, it’s so warm. And you don’t have to wear Uggs (why why why would you wear them?)! La Canadienne, Fluevog, Pajar, Palmroth (my personal fave), sometimes Born (not the warmest in the world but good for getting from the cab door to the restaurant door) make warm, nice-looking boots. Wear a proper hat with a brim or a cloche instead of a tuque and get beautiful scarves and gloves. Don’t despair! You don’t have to look frumpy!

      As for #2 on Leandra’s list: this is just silly. Men have been wearing suit jackets under their coats for yonks. Get a better coat.

  • Kay Nguyen

    Even though I hate cold weather but I’m a huge sucker for cozy sweaters! They look amazing on everybody <3


  • Asshly

    This is the winter wardrobe bible.


  • Gigi

    I might not be able to show off my embellished blazer, but at least I can wear middle school charm bracelets up & down the length of my long-gloved wrists & tie a chaotic-colored scarf around my head. complete with Art Mom homemade earrings & Im set……… Plus, a statement boot with christmas socks (you know.. the fuzzy hot-chocolate-at-home ones…) inside is the only way I survive New York Winter & all her cruel cold charms with style

    • Zauberwald

      This outfit sounds like an absolute mess… I bet it’s divine!!!

      • Gigi

        Yes! What’s comforting about outward mess for me is that it’s honest.

        • Elle

          my vision of a perfect winter wardrobe has always included a slightly vintage-y coat with shorter, wide sleeves that i can wear with elegant long gloves and bracelets/bangles! SO GOOD!

    • Elly

      That outfit sounds fucking awesome

  • cicillionaire

    I live in MN, and winter can be a humbling experience for even the most hearty fashion lover. There are really only two options, be cold or layers. You just choose. I choose CuddleDuds every damn day until April(May). And snowboots, because ruining your shoes is just out of the question.

  • Sophie Kreuze

    Thanks for clearing number 8 up! I always thought the problem was me.

  • CRIES I feel like poop in winter and then start believing I am poop. Need to start thinking I am SURVIVING.
    Generally I wear knitted leggings, thermal top, and jumpers. Mix and match. I have one pair of platform ‘walking boots’, a pair of fluffy slippers / slides . Thigh high boots but they don’t go with all.
    Sandals and socks are a spring and autumn time for me .
    By the end of the day I feel like my body is tired from the clothes .
    Glad I am not alone .

    • This year I have extended accessories from big fat faux fur gloves and a faux fur furry hat to a big blanket scarf from Zara .

  • I’ve definitely gotten a few blazers under winter jackets, but granted it is hard! And static – so right! What kind of stretch pants do you like? It’s fashionable if I got it from you!


  • Ania

    Silk in winter IS the best, but must be layered wisely. Keep it close to your skin and it will keep you warm. When really cold, I use no other but silk leggins under wool trousers or jeans. Silk base layer under any silk or wool top makes me warm and comfortable.
    Also, dont forget that cashmere is ment for winter, and you can properly tuck a cashmere sweater in your jeans.
    Recently I discovered yak cardigans, extremely warm and chic.
    With silk, wool, cashmere and yak I cannot feel not chic provided I’m wearing my leather, water-resisting, high boots.

    • Gigi

      Do you recommend a particular brand of silk leggings?

      • Stephanie

        Many people SWEAR by LLBEAN!

      • Ania

        I got mine at tkmaxx, they are from Lady Avenue.

  • MsGorman

    I am SOOOO feeling this right now!

  • Bernadette Aylward

    GOD BLESS it’s all true. and I find myself especially challenged for days when I must spend time inside AND outside-I can dress for one type of activity at a time in winter (See: wearing velvet pants and sneakers at a NYE bonfire). long underwear-good for being outside, but when I start to sweat its a layer you can’t take off!!!!!! AHHHHHH
    but I do love the atmosphere of winter and looking at snow…probably ok that I live in the south


    You are a genius! You’ve put into words what so many of us go through EVERY winter! If only I could afford, and my conscience would allow, a beautiful and stylish winter coat with perfectly matched footwear for every blasted shirt, sweater, pair of slacks or jeans, skirt or dress I EVER wear. See…the solution is so simple.


    Oh…and of course I would need a separate set up for every possible degree change winter brings…50 today….-1 next Tuesday. Summer…please come early!

  • Anna Curran

    I live in Ireland and there is almost no difference in how I dress in winter and summer, bar gloves.

  • starryhye

    These reasons plus many more are why I moved to Arizona. Winter is the pits. Of course the flip side to that is in July when I have to wear clothes in public when it’s 115*…

  • diandra williams

    Wow this is some read. How many of us women can relate to the lies we tell ourselves about our winter fashion choices. Thanks for writing about what we all were thinking but never said.

  • Kalei Buczek

    @leandra pls provide more *chic* balaclava alternatives. the one you don is sold out 🙁 🙁 🙁

  • Emily R

    I feel so much better that you’ve said all these things out loud! I HATE winter clothes for all the reasons below. I feel like an asexual frump. And there’s nothing cute about all my salt splashed pants and boots. Ugh!

  • MargotSilentT

    Can anyone tell me where the orange earrings Leandra is wearing in the photo on the homepage linking to this article???? ( in the fur coat)

  • Ana Beatriz Quinto

    Love this hahaha and it’s so true. I’ve spend my real first winter in NYC last year and finally understood that it’s really hard to wear the oufit that you dreamt of in that weather.

  • Haw! Haw! Haw! ‘Love it!

    I live in Berlin, people tell me that in winter, I’m always dressed as if it’s summer! I blame my British upbringing, I’m from Northern England you see… And I don’t believe that I’ve worn a sweater in 20 years! Far too bulky and itchy. I wear lots of jackets though, and when I do, I leave my coat at home, wrap a scarf around my neck, walk really fast, and pretend it’s not freezing.

    Oh, and I’ve stopped wearing tights in the winter too. I usually wear skin-toned ones but people hardly noticed that I was wearing them anyway ‘cos I live in Berlin (ahem!), so I wear long trousers and tuck my socks underneath them instead!

  • Ruth Winter Wolfe

    I’m a Colorado Gal..we’re expert at cold weather dressing. We wear Jeans and sweaters. And good warm coats. And hats, and gloves, and wool socks . It’s cold! Save the fluffy sleeves and sexy sandals for Summer and stay warm 🙂

  • Hannah KC

    I need this article but in reverse, currently surviving a mega heat wave in Australia and have NO IDEA how to create an interesting, chic (for want of a better word) outfit without melting into a puddle of sweat. Meanwhile I’m wistfully planning all my winter looks and day dreaming about wearing layers again. It feels like the day will never come.

  • Kara

    I must say, I am grateful to mother winter because I fall in deep love with my favorite pieces of clothing and want to live in them until they fall apart. Nasty weather seems like a good time to wear the same leather investment jacket, wool sweater and honeycombed black skinnies EVERY DAY (get my moneys worth because winter clothing is expensive!). Last year, though, I had one boring synthetic and unflattering jacket and ugly hiking boots and was depressed as fuuuuu. Living in the PNW for my second year has taught me to go against the grain and steer away from the skittle-colored puffer jackets (boring :/) and invest in one or two amazing jackets instead of a bunch of meh clothes. Am I the only one who loves an excuse to wear a favorite outfit for dayssss?

  • Keisha

    Winters here in BC are rainy, I yearn for wide leg pants but that could spell disaster so I stick religiously to my uniform of skinny jeans with ankle boots or tucked into rainboots. I layer up on top to keep out the damp chill and top with a knee-length coat. I’ve got three colourful coats in rotation to keep things lively and stick to black hats, bags and umbrellas

  • Manu

    Soooo true! I am living in a ski resort but still love fashion and am always in a style rut during winter time… Sensible shoes and cropped high waist, wide legged pants just look awkward….Heels? Leather soles?… Bags with no crossbody strap slide of the shoulder or lead to freezing hands… But at least long puffer coats are very chic at the moment!…

  • su

    YESSSSSSS! So true…. but don‘t set hope on summer! Loving layers is challenging both in winter AND summer!!! In summer, drowning in my own sweat, I am hopelessly waiting for the cooler months to come – and when they arrive, the aforementioned problems occur.
    😉 su

  • Basil

    So how do you dress for winter? I grew up in a hot country and despite living in the U.K. for a while now, I still don’t get it. I’m either freezing my butt off or get too enthusiastic with layers and end up grumpy and stripping clothes off as soon as I go inside anywhere. It doesn’t help that lots of shops have their heating set to “stiflingly hot”, and the tube is a sauna. Both my husband and I are seriously considering moving country we’re so fed up with it. Also – we have a toddler and a baby. It’s enough of a pain dressing myself in 20 layers to leave the house, but add in wrestling a toddler and a baby into them as well … forget about it.
    Summer is SO much easier, even the heat wave we had in London (and I was pregnant!) was easier for dress for – cotton a line dress, nice sandals, fancy jewellery and you’re done

    • Lizzie

      After going back and forth from the UK to Spain for 5 years of my adult life and DYING everytime I got off the plane in London, here are my British winter teachings:
      1. Get a jazzy coat that you won’t loathe to put on (60% wool or higher)
      2. Always have a down layer with you, something thin that you can easily wear under your coat, but packs up small. Uniqlo and Gap usually have lots of options
      3. Only wear shoes or boots that are waterproof. They can be shiny and interesting but waterproof is key
      4. Wear wool tights under your trousers on especially cold days. Nylon ones will be sweaty and static once you go indoors
      6. When you enter anywhere, especially the tube, remove said scarf and your coat immediately, and lay it over your arm. You will never regret doing this.
      7. Carry a cool yet volumous bag to store backup hat / gloves / earmuffs / umbrella
      8. Fun earrings and tinted lip balm in a bright colour (Burts Bees is great) are your friend.

      I think this list will go out the window now I have New England winters to contend with, but you should survive a London winter. Good luck! x

      • Helen

        Thank you for #6! I’m a Londoner and get so cross with everyone keeping their coats on on the underground, with all that excess body heat making it feel like August down there… Ugh I love to hate the underground.

      • leilanigl

        Yes! Especially 4. Cottons, linens, silks and wools as underlayers will almost always be better for sweat & temperature regulation than most polyesters/rayon/nylon/etc. I’ve stopped buying those dresses/floaty poly blouses from Zara (sob) because I just can’t wear them in the winter/fall under things, they get too sweaty when you’re layering up and down. There are a few exceptions like certain workout or technical fabrics, but I’ve become super picky.

  • GiGi Crawford

    From Columbus,Ga
    My chicness go to in the winter are my gloves. They complete the outfit with sass. “Hands down” It’s a fetish Over the years I have a collection now up to 20 pairs… I found a cute cheetah velvet pair at TJ Maxx that I adore.

  • leilanigl

    In all seriousness, get you a pair of proper long johns from MEC, none of this tights/other leggings nonsense, and do not for any reason go for the nonsense merino/wool 200$+ fashion ‘long johns’. Too bulky and static-city, they don’t get it done. The 30$ MEC-brand ones are on a totally different level: seamed to move underneath anything (aka my fancy tights, fashion-y leggings, skinny jeans) and super warm. Uniqlo probably has something similar? Idk we don’t get that here yet.

    Love, a cranky Canadian who has been wearing long johns under everything for a month already.

  • Diana

    I want that vintage looking outfit from the pics, boots manish pants and something that appears like a shawl transformed into a bikini top, never seen that one before, just cool

  • Suzi q

    Thanks. For ALL the wonderful ideas as us women can use ideas in comfort and style when it’s 0 degrees out.

  • antonio manzini

    ahahahahahahahah I spent a lifetime dreaming to look chic in silk and heels in winter but I never was brave enough….

  • Jessica Downing

    Growing up and living in Portland we luckily don’t get a lot of real winter weather and I can get away with wearing most things year round and don’t have to worry about bundling up (Which is great!). I’m moving to Minneapolis this summer and I’m kinda dreading having to adjust to such cold winters and not being able to wear whatever I want!

    • Kiks

      Oh my gosh. Can we be pen pals. I have lived on the west coast (currently on Vancouver Island) for seven years…and this summer I’m moving to Manitoba. I don’t even know how I’m going to live. Yesterday I was wearing a leather jacket and a t-shirt.

  • Jelena Garic

    i feel you @LeandraMedine:disqus, in toronto, like NYC, i basically have to choose an ‘exterior’ look – jacket, boots, cute scarf, mitts/gloves, hat and a statement lip – or freeze to bits between warm, cozy buildings 😅

  • Catherine Bohner

    When I want to skimp on a coat, I wear a really good thermal athletic/camping base layer under whatever I want and say screw you winter. Bet you could rock a blazer as a coat that way for most of a NY winter.

    Pumps and sandals though, yikes.

  • Thamsa

    In Canadian winter, I always have a silk scarf around my neck. Especially when I have to wear my serious winter coat. It has such a high neck, that thicker scarves wont allow me to zip it up all the way. Silk is a natural insulator like wool, so it’s always a great choice! Scarves are just about the most exciting part of my winter wardrobe. I am excited so be spending the next couple of winters in South Africa, so it’ll be fun to play around with style with the new winter climate.

  • ziggybk

    Add Uniqlo heattech to your layer system and you can make the blazer work as an outer coat! Heattech long sleeve top + thin wool sweater (like 100% wool or cashmere, acrylic won’t cut it) + blazer + scarf = warm enough to make it to your subway stop without freezing most days this winter!
    Also, if you keep your extremities warm you need less bulky clothing. Cover your feet in wool socks (smart wool or icebreaker are good brands, expensive but they last forever), get a good pair of gloves with fleece lining (or layer up a thin silk glove liner with leather gloves), and cover your head and ears (not always the prettiest choice but that’s where you lose the most heat).

  • Merino wool is the prime fabric of freezing temperatures. Over and under everything! Sometimes in Montreal we wear two or three turtlenecks at a time. A different colour peeking out under a rolled neck is cute.

  • Carlee Gomes

    Leandra, you are simply the best.

  • Xenita

    I love dressing for winter because it already gives me a set of essentials (red waterproof chelsea boots and a big honkin parka) that i can then use to pair an outfit with. Am I in the minority for thinking parkas are actually really chic? they remind me of romantic ski excursions when you’re not skiing.
    But yeah, the whole ‘how to wear a big sweater under a winter jacket’ is a real problem. like, what am i supposed to do with my blazer, carry it? Last winter when I was in Paris, I thought I’d wear a chunky sweater under a sleek camel jacket for the whole week I was there. In pictures I looked SWOL AF.

  • Jay

    Agree so much. Especially on the blazer thing. Like how am I supposed to get that under my down coat?! And the latter I certainly need more than the former… so that one keeps hanging in my closet till… better weather?

  • Cattja L´esh

    Heaven! Thanks for this list. Every item on it was a huge relief. I always felt like the odd one out who didn´t know how to fit that blazer under my coat or how to pull off velvet socks in pumps. Winterfashion is a fraud. I am doing my best to ignore the season by sticking to my flat suede sock boots pretending they are suited for winter (LOL). Other than that i am a member of the sneaker and (thick-ass) sock movement. Wearing a boring pleated trouser+turtleneck uniform since months, i only step up my winter game with (very) tall and chunky woolly caps. Need to mention #lovesummerhateeverythingelse – cant wait.

  • Barbara Acevedo

    Thank you for this article!!!!! “Instagram winter fashion” frustrates me.

  • Adelle (Fashionista Lab)

    All of this is so true. I wore a blazer over a t-shirt to a party on New Year’s Day, and it definitely felt awkward under my coat. And then, even though I specifically wore the blazer as part of my outfit, it was so warm inside that I took it off, anyway, thus making the arm discomfort all for naught.

  • Pia Sophie

    i love this. thank you.

  • Tara Jayne

    New Yorkers need to embrace the Canadian parka! You can wear whatever you want underneath it, especially if you buy it a size big! It’ll change your life. We have the same weather in Ottawa and I honestly cannot imagine functioning without mine. Sure it’s a bit boring not at all sexy etc. Maybe I just killed it with that last sentence 🙂

  • ladle

    Huh, I like the look of a skirt peeking out from under a coat. And winter is great for wearing all your favourite soft tops together all at once. Yay for layers.

  • I would call my style lazy chic, meaning it’s mostly a black blouse, black pants, and some flats. So, getting ready in the Winter is definitely a chore because then you have to get out your boots and socks and everything. However, I do feel like I’m more creative in the Winter because I love darker tones. However, getting dressed in the Summer is a very different story!

    GG | http://www.girlingamba.com

  • Neats

    Sooo true. I am in Chicago and aggravated by “great winter looks” that involve, 4″ heels, sleeveless dresses. coats we all know will never work if it is below 45 and/or you are doing anything more than running from the Uber to the door, no gloves, no scarf or anything any northerner knows will not be warm enough for winter temps or will have falling on your frozen butt if there is any snow. It is insulting that someone truly thinks we appreciate these suggestions that come winter after winter after winter.

  • You had me at 1). OH MY GOD. This is ‘the year of the sleeve’ and my question has always been: how the hell do I get that into ‘the year of the skinny coat’? Thank you. I thought I was losing my mind.