She Who Wears A Hat

Has a special je ne sais quoi about her, doesn’t she?


I walked into a department store last Friday dressed rather regularly in a pair of black jeans which have been aptly named the “tomboy jeans” by Blk Dnm’s Johan Lindeberg, worn with a white button down blouse, a grey jacket and red, sparkly-ass ballet-style short heels. I was wearing a wide brim hat and holding a red bag, which in hindsight looked grossly coordinated with my shoes. You live and you learn, right?

“How are you today?” an earnestly polite salesman asked while I thumbed through a rack of navy blue blouses.

“Well, thank you,” I responded, to which said man retorted, “It shows.”

The pithy exchange was endearing. It felt like one of those great New York moments that make living here worth it by simple virtue of receiving confirmation that even when considering the tiny things, like an unassuming spectator who completely gets your aura, there’s nowhere like it.

The thing is, why — or how — did my over-well-ming sense of eudaemonia show? I wasn’t particularly put together save for the aforementioned sparkly-ass shoes. At this point, I’d had lunch so my blouse was stained in four places and if I’m going to get really honest with you, I hadn’t showered in like, five days. (Blog research! You’ll see!)

I surmised that it had to be the hat. It had been presenting nuanced challenges all day (do I take it off when I get on the subway and if so, where do I put it? Are these people looking at me because I appear so damn affected? Now that I’m seated indoors and at a meeting, what do I do with the hat?) but this correspondence seemed like the most blaring indication that to wear a hat is not just to make a statement. It is to yell that you are the type of woman who knows how to pull off a hat. And so, by the power vested in your indispensable swag, you will.

This point has only been fine-tuned by a perspective that Charlotte offered on hat-wearing and the popular stereotype that when you wear one, you look like an asshole. (Asshole in both senses, meaning that you are probably a dick but also a moron.) She said that the reason hat-wearers probably appear as they do is because wearing the topper takes a lot of confidence. Enough, at least, to seriously believe that everyone else has got it wrong, but you’ve got it right. In the spirit of emulating that confidence in order to possibly accrue some of our own, you’ll find three looks styled with the very hat I wore last week.

new hat3

In the first instance, I’m wearing the same grey Hanro jumpsuit I slept in the night before, which I have said on multiple occasions that I love because it makes me feel like I am in the fetal position. This look is meant to encapsulate that Friday morning oh-my-goodness-it’s-not-the-weekend-yet?-What-do-you-mean-I-have-to-get-up-and-ready-for-work pre-day coffee run. You throw a denim jacket (mine is Acne) on over your pajamas and a trench coat (mine is by Mina & Olya) on over that and because you haven’t washed your hair in a week (blog research! You’ll see!) you effectively need a hat. The sneakers (Converse x Missoni though Free Knits should do) provide a nice contrast when considering how otherwise “formal” a wide brimmed hat can be, and the Olympia Le-Tan clutch is essentially just foreshadowing scenario #2.

new hat5

You probably know by now that this blog is underscored by a deep, insatiable hankering to tango with Sarkozy so this scenario demonstrates how to wear a hat when you’re trying to look impossibly French. That’s why my facial expression denotes a sense of perpetual ugh-ness. Get it? Got it? Good. The cropped white blouse is from ASOS, the high waist jeans are by Blk Dnm, the grey jacket is from the Isabel Marant pour H&M collab-o-lab and the shoes are last season’s Marant — hold the H, hold the M.

new hat9

In a final scenario that may or may not get you ready for resort, it’s important to remember that because the preferred headgear makes such a statement you either have to let it speak by muting out its surroundings, or give it reason to want to get louder. Here, it’s paired with a balloon sleeved off-the-shoulder blouse by Vika Gazinskaya and Theyskens’ Theory wide leg pants. Sometimes it’s okay to, instead of speak for your look, let it speak for you. Knaaamean?

End scene.

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  • Quinn Halman

    I found Carmen SanDiego! But actually, you looks so cool

    • Thamsa

      I was thinking the exact thing!

  • Hayley Mitchell-Gardner

    i actually looove all three of these outfits! They are awesome 🙂 i love hats they can add soooo much to an outfit! And can change the look of it instantly

    Hayley xx

  • Natali

    2nd outfit is the BOMB!!

  • leChat

    Yo, sis: pls post a pic of the outfit you were wearing when the sales dude told you your well-ness showed !

    (We love that guy, btw.)

  • marina miouprincess

    love the 3rd outfit,the hat is divine!

  • tittle hats
  • monkeyshines
  • The second one is kick asshole great!

  • Brittany

    I am glad you also didn’t know what to do with your hat when going on the subway etc! I recently bought a black fedora when I was in London and wore it in London and Paris (cos I like hats, they are practical when it is cold/raining, and to make myself that little bit more stylish :)). When I went somewhere to eat, or just inside, I wouldn’t know whether to take it off or not – it is part of my outfit! So at meals I would, but I left it on for the tube. And side point – I did have a French boy come up to me and tell me I looked beautiful (in a non sleazy way) when wearing it in Paris, which I’m pretty sure wouldn’t have happened without the extra mystery of my hat 😉 (unsuccessful man repelling there).

    • Kirsten

      I recently wore a wide brim hat to the Spring Racing Carnival in Melbourne and struggled with hat etiquette as well. To kiss people hello I had to lift the brim otherwise I would hit people in the head with it! Wasn’t as glamorous as I envisaged.

  • I LOOOOVE HATS! I have a fascinator that I have yet to wear because I look like an ass hole wearing it with my everyday casual attire. Help!

  • brooke

    im glad you did some exploration on this, i’ve worn hats 4 days this week (because I’m a mom with no time to wash my hair) and every day I’ve worn one several men have complimented me on them…EVERY single day….

  • Katerina

    Amazing looks!! 2nd and 3rd outfits have won my heart!

  • Savannah

    I’m not particularly sure why, but that hat gives me a “smooth criminal” kind of vibe, if a smooth criminal just woke up and didn’t take a shower or wash his/her for the past 5 days. Also, is it bad that I completely skipped all the way to the bottom of the page to see that that magnificent blouse was crafted by Vika Gazinskaya? Really though, that blouse is stealing your hat’s shine bro.

    • Savannah

      Also, where can I find that Vika blouse? Like I said, it’s magnificent bro.

      • Jessica Rose

        Ha! Thats really funny! Smooth criminal..;)

  • Leila

    What department store were you in?

  • Hudson Berry

    That Vika Gazinskaya blouse with wide legs… daddy like.

  • Amelia Diamond

    I wanna wear your hat. – Joey Tribbiani

  • Nico

    Stylish! I really like the first outfit!

    New post on lowbudget-lowcost Fashion Blog

  • Love a good hat. Perfect for awful hair days when you haven’t washed your hair in days.

  • Brigita Dambe

    Leandra, you have a wide range of followers and you can raise awareness. Please help Latvia and your fellow people in any way you can at this difficult time!


  • Charis

    my favourite is your 2nd look! great touch with the grey coat and some awesome boots to go along.

  • I love me a good wide brim hat because it’s cheaper and easiest than any weight-loss/ plastic surgery regime.

    Everyone looks good in one!

  • Aubrey Green

    I love hats, I look good in hats, but somehow I don’t own any. I think it defintiely takes confidence to wear them. You of course look amazing.

  • I love all the outfits. In the first look you’re from Copenhagen, in the second look you’re from Paris, and in the third look you’re from London (OR one of those eccentric NYers that Bill shoots regularly in old Yohji coats on 5th Ave) — or at least that’s my interpretation. Loving the hat & the globalization, yo.

  • Eve

    I had a friend who, whenever she was on vacation, would put on a hat and not take it off for the next 2-4 weeks of her stay. Was she pulling it off? Perhaps… Did I pull it off when it was my turn to take a walk on the hat rack green mile? Not so much. But I did get some kickass shots for Instagram.

  • Jane

    I’ve always wanted to wear hats but was afraid of looking like an asshole. I’ve gotten over it now and am saving up for a nice cloche like what Angelina wore in The Changeling.

  • Char

    I love the hat–great colour. I have about 20 of them and never had anyone say I’m an asshole either (though maybe they’re secretly thinking it?). Little old ladies always tell me they love them. 🙂

  • Dee

    Love love love hats Leandra.
    But one question for you, how did you wear that off-the-shoulder blouse any day of the week this week? It was freezing cold!

  • Suzy_Q

    On a tangent – only because your post refers to boutique sales people and long intervals between showering – a friend of mine told me a story. Quite respectably dressed in a Zara top, Joseph gabardine pants, Stuart Weitzman flats and a Fossil handbag, she recently went to a boutique (specialising in Armani and Zegna suiting for for both sexes) and spotted a stunning pair of silk Armani pants, but was rudely asked to leave because of her supposedly “strong B.O.” by a snooty middle-aged sales lady. I mean, we live in Australia where it does get really hot around midday and the stark contrast of skyscraper air-con and the great sweltering outdoors might precipitate a sudden surge of perspiration…but aren’t there nice less-offensive ways of dissuading patrons of the establishment from trying on merchandise? Worst of all she was planning on also picking up a few Christmas gifts from the men’s section for her boyfriend….until she was forced to take her patronage elsewhere.

    Moral of the story – LV handbags are not always accurate indicators of whether their owners will actually buy stuff. Like seriously.

  • Amazing pictures, you look fabulous Leandra!

    Mafalda ❤

  • dupras

    I’m feeling very hat inspired now, the second look is absolutely spot on! I’ve never been a hat wearer and it’s because you’re 100% right about the confidence thing. Have to find me some headwear asap..

  • Sasa

    I love outfit three soo mucho.

  • Amelie
  • Love all three looks. I love hats … more on the others than on me. Probably because I feel constrained, but I might reconsider hats in the future.

  • love the hat!

    Valentina Duracinsky Blog
    Facebook Page

  • lovemesomefashion

    dang girl you are so fly! best dressed blogger out there for sure!

  • Marta Pozzan

    Looking like a serious #manrepeller in that green top

  • Amiee @ 24hourfindings

    After 23 years i’m yet to wear a hat in public without my mother having told me ‘it’s because she says so…’

    Maybe this Winter will be the year I brave it!

  • Marc Ferraz

    You’re probably the most original fashion blogger I read, I love your writing style… and your style style too of course. ^^

    • Alexiada

      she really is, no? unique

  • Maral Halliyeva

    I’ve been obsessing with my new floppy hat from the second I got my hands on it. I didn’t even bag it after buying it, it went straight on my head! I love your last outfit, it is so elegant. I find styling hats such a creative process!

  • Stella

    Love your second look. You know just the right ways to incorporate menswear into your everyday looks!! xx

  • Obsessed with the second look!! Those white boots just look impossibly cool on you. =]

  • Monika Jones

    Love the third outfit! Great styling

  • EtralaLondon

    I have fallen in love with the green blouse.. it’s just amazing!!!

    I would love to see you wearing ETRALA one day!!

    from London xx

  • Alyssaspeaks

    My immediate thoughts. Leandra, HOW DO YOU GET AROUND in these fantabulous getups? I realise you said subway in this post but do you? Really?

    I could never wobble around in the subway in my 4-inch heels, especially not if I have to add floor-sweeping pants to the mix. A post on how to navigate the transport system in the most impractical clothing pretty please?

    If Leandra has done such as post and I’ve missed it, someone please enlighten me.

  • Maha

    so… did you leave the hat on when indoors, or is that like an old fashioned rule (similar to the one about not wearing white after labor day)?

  • Selena Aponte

    Finally, I’ve been waiting for an article about the culture of hat wearing. I, an avid hat wearer confidently donned my Preston & Olivia wide brimmed fedora all over Paris & London and although I did receive a few wide-eyed stares, people did approach me with complimentary notations. Maybe it was Paris that furnished the confidence I needed to pull off my look and London that reinforced my sartorial splendor.

    In New York, I’m really just an asshole who thinks she’s better than everyone else (at least on the train) and from the jokes my family makes about looking like Freddy Krueger, Crocodile Dundee, etc. I guess I’m kind of an asshole to them as well..

  • Jessica

    `That last outfit though! Absolutely spectacular.

  • Amna Khan

    All hats are very coll

    i like all


  • Grace

    first the worst, second the best, third the golden princess… literally applies to this series of photos. I mean that in the best way possible. Look #2 is super kickass. So frenchy, so chic.

  • Leah Pearlstein

    What a coincidence that you posted this so recently because I, Leah Pearlstein (15 years old), went to a Chanukah Hockey game the other night and decided to be a brave one and wear my newly purchased black hat from Nordstrom (not to be mistaken from the classic Chabad “black hat” – a woman from the Chabad community actually asked me if I was wearing my father’s old hat). NO, obviously I was not but I guess I was asking for it. I am proud to say that I kept it on the entire night and it actually made me feel more confident that I was not afraid to wear what i truly loved. Thank you for being you, Leandra Medine, and being so relatable. I know it is cliche’, but you are my inspiration.

    PS. I read your book. Hands down the most wonderful thing I have ever read (not that i have read much in my lifetime, being alive, you know, not very long). Thank you for writing “Seeking Love, Finding Overalls”, and I plan to read it over and over and highlight my favorite parts. I think you have changed my life.
    Sincerely, Leah

  • flofrog

    Love the middle photo. Love it.

    Love that kind of surgical half gloves/forearm covers

    very endearing

  • Hats. I really try, but I can’t bring myself to buy them. I try them on, and I feel okay, but I look in the mirror and it looks like the hat is about to burst for the sheer size of my head. and once in a while it feels that way too. I have a fairly big head (and that’s even when I don’t have the added volume of braids), but if it feels okay why does it look so strange? It’s weird. In other news, you are rocking all of these. #2 is my fave.

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  • Beth

    I just love all these outfits!
    Panama Hats