7 Truly Excellent Winter “Going Out” Looks
01.22.19

Take it from me, a person who has tried numerous times: you can’t stay inside your apartment all winter. Sometimes your selfish friends have the gall to throw a party or invite you to dinner! There might be a band that was confused and scheduled a concert when it’s snowing. Maybe, you’ve temporarily taken leave of your senses and decided that you should go dance and meet new people. Whatever the occasion that is taking you out of your home in the dead of winter may be, you gotta get dressed! Which is hard. To make things a little less hard, I asked seven extremely stylish folks to tell me how they get dressed to go out in the winter.


Wanyi Jiang, Design Director at Marie Claire

Realisation Par dress, men’s aviator jacket from a vintage shop in Paris — similar here, Valentino boots, Jennifer Fisher earrings, Wolford tights, Staud bag

Precisely how many layers are involved in your winter ‘going out’ outfit?

Four! Jacket, dress, tights, boots. I usually am the layer queen. I’ll wear three cashmere sweaters out under a vest and a puffer jacket with a hat on top. But because this is going out, I consider the look cab-to-curb only. Two minutes of standing outside and boom, I’m in. Any cold issues will be solved by alcohol.

Why is this your ‘going out’ look?

1.) Because it’s black, whatever you spill on me will be okay. 2) Because it’s cotton, whatever you spill on me will be okay. 3.) Because it’s a nice silhouette but it’s not TOO slutty. Believe me, I’m all for slutty, but sometimes I can’t be bothered with skin oozing out all over the place. A tight dress is enough and the over-the-knee boots are mid-heeled so it gives me a lift, but my feet don’t hurt while I’m drunk-hailing a cab home. I *will* be cold so I will be jumping into a cab ASAP.

P.s. I ripped my tights while photographing these so basically yes, wear things you can kind of part with but look good on your body.

How would you describe your winter ‘going out’ philosophy?

Believe it or not — blend in. The older I get, the more I want to have intimate dates with friends instead of hitting the club. Even saying “hitting the club” sounds weird because I don’t do that. I want to sit in the corner and get into a deep conversation. Or talk to the waiter about Justin Bieber? (This has happened once). But you want to look nice so that should you decide last minute you want to pretend to be 21 and go buck-wild, you can get into a super bougie place. Just be prepared.

What’s the ‘going out’ spot that is most likely to get you out of your home?

Honestly, wherever the music is good and there are places to sit down. Wherever you don’t have to wait in line and they serve drinks in wine glasses as big as your face. I don’t know why; I just like the proportion of a huge wine glass to my face. It’s like drinking from a fishbowl and it’s fun. The last time I went OUT out was with my friend to Rin Tin Tin. We sat at the bar and talked and took embarrassingly silly selfies. Because the most important thing that will get me out of the house is the good company.


Audrey Williams, Branded Fashion and Beauty Editor at Bustle

Precisely how many layers are involved in your winter ‘going out’ outfit?

Alright, so boom, the first thing to know is I hate winter, I hate being cold, and I hate having to layer clothes. That said, if I must go somewhere, layering is non-negotiable, and so, I have a formula. The first layer is always a Uniqlo Heattech camisole that I wear as the first barrier against cold. Then, with this particular going out look, I saw an opportunity to add another layer of warmth in the form of a knit tank dress. Those are the layers you can’t see that are actually doing the heavy lifting to keep me warm. Then came the turtleneck under a slip dress under the coat, so ultimately five layers. It’s all about balancing the seen and unseen layers.

Why is this your ‘going out’ look?

Wrinkly slip dresses were my summer aesthetic, and in a stand against winter, I refuse to give them up. This one is my favorite (it was my aunt’s) and it lends itself easily to winter layering. The turtleneck is really just worn out of necessity, and so I can feel my R&B-singer-from-the-90s fantasy. The finishing touch was to throw on my ol’ faithful leopard faux fur coat. When all else fails, just ask yourself, WWMJBD? (What Would Mary J. Blige Do?)

How would you describe your winter ‘going out’ philosophy?

Don’t. Don’t go out.

What’s the ‘going out’ spot that is most likely to get you out of your home?

It’s not so much particular spots as it is particular people. I’m not leaving my house (outside of work and errands that are essential to life), unless I’ve been invited somewhere by someone I genuinely care about. Unfortunately for me, a lot of people I love have winter birthdays, and I’ve had to make peace with celebrating them despite the weather.


Georgia Graham, Writer and Model

Precisely how many layers are involved in your winter ‘going out’ outfit?

Three layers, four if you count my underwear. I try to dress with potential for undressing — that sounds saucy but it’s actually just in case I get hot. There’s nothing worse than removing a layer and your whole look disappearing. Outsmart practicalities at all costs!

Why is this your ‘going out’ look?

This suit is always a winner — so far I’ve taken it to a friend’s wedding and my Gran’s 90th. I think black turtlenecks are always chic and although it looks like there’s a lot going on, it’s actually a very easy outfit to dance and move around in.

How would you describe your winter ‘going out’ philosophy?

Shrek said that ogres are like onions, but I also believe this to be true of winter ‘going out’ looks. Layers are key.

What’s the ‘going out’ spot that is most likely to get you out of your home?

A good electronic music or techno night will always get me going. If that’s not available then anywhere I can dance really, or just have fun with friends. I love going out so it doesn’t take much to twist my rubber arm, even in winter.


Simedar Jackson, MR’s Partnerships Strategist

Precisely how many layers are involved in your winter ‘going out’ outfit?

Three. I’ll typically layer my shirts or go for a thinner long sleeve with some type of jacket before the final coat layer. I definitely don’t layer as much as I should because I’m terrible at dressing for the weather and also most going out spots I’m hitting get really hot inside. When I get dressed I think the most about layering enough to brave the cold but not too much so I can still breathe when I’ve arrived at my destination.

Why is this your ‘going out’ look?

I love this look because it gives the illusion of try-hard but with peak comfort. Nothing is too tight, lots of things are stretchy/soft and the shoes are chic yet very sensible. The only item that breaks with tradition here is the snakeskin top because it was my NYE look and I had to do it to ’em just one time.

How would you describe your winter ‘going out’ philosophy?

My winter going out philosophy USED to be “YOLO.” Now, it’s more like “I’m already in the bed.”

What’s the ‘going out’ spot that is most likely to get you out of your home?

Anything that promises free drinks or food.


Ansley Morgan, Freelance Writer and Stylist

Precisely how many layers are involved in your winter ‘going out’ outfit?

One layer on the bottom and two on the top. I am hot natured, so two layers is normally my happy place.

Why is this your ‘going out’ look?

When I go out, I like to dress for functionality. I do not want to have too much stuff to keep up with. If my jacket has plenty of pocket space, I am going to leave my purse at home. This Eckhaus Latta jacket is perfect because it has four roomy pockets that replace any need for a bag. Despite it being cold, I still want to feel sexy. In order to spice up this look I paired it with a sheer mesh top from Yigal Azrouel and boots from Stuart Weitzman. Overall, this outfit makes me feel good about myself and prepared for a fun night out.

How would you describe your winter ‘going out’ philosophy?

My philosophy is to wear whatever I want, regardless of the cold. I tend to dress for my mood instead of the weather. I typically wear some version of a top with jeans and boots, so I have a nice base layer for warmth. This past weekend I went out while in NYC and did not even wear a jacket. It seems silly to go without one, but I was only cold when relocating to different venues. What matters most is that you feel good in what you are wearing, because that can make or break your evening.

What’s the ‘going out’ spot that is most likely to get you out of your home?

Starting the night at Creature Comforts brewery with my friends and ending it dancing at my favorite bar, Little Kings.


Stray, Stylist and Style Blogger 

ASOS turtleneck, ASOS pants, Zara men’s belt — similar here, Buffalo London shoes, Zara men’s coat — similar here, gold chain from Buffalo Exchange with Louis Vuitton lock, Forever 21 socksglasses from Amazon

Precisely how many layers are involved in your winter ‘going out’ outfit?

I’m only wearing two layers for this look. Whenever I go to a bar or out dancing it’s always warm inside the bar because the heat is on. You’ll also naturally get warm from all the dancing if the heat isn’t on. I like to wear the least amount of layers that allow me to stay warm on my subway ride but I’m also not too warm to the point of sweating.

Why is this your ‘going out’ look?

It’s simple and I love a nice clean black-on-black look with a camel coat. I try to keep it simple when I go out because I like to save my colorful clothes for the day time. When I’m at a bar, whether it’s my drink or someone else’s, something spills. It always seems to happen when I’m wearing a lighter colored top or pants. I can avoid having these accidents ruin my outfit when I’m wearing all black. Also, black on black is a polished look without even trying! I’m obsessed with my Buffalo London matte black sneakers. They have so much height (I’m short so I appreciate that), they’re comfortable and it’s a fun shoe. When I wear all black I like to add a necklace to spice it up a bit so I chose my favorite gold necklace right now.

How would you describe your winter ‘going out’ philosophy?

The place I’m going can’t be more than 30 minutes on the train because I live off the L and the G train and I have to spend quite a bit of my time walking outside to get to the train. My goal is to spend the least amount of time on the train! Also, if possible, I try to go out around my neighborhood. I like to go to places with good music, preferably 90s/early 2000s. It’s so much fun seeing so many people singing along to the same songs you grew up with!

What’s the ‘going out’ spot that is most likely to get you out of your home?

There are so many cute bars around Greenpoint and Williamsburg. I really like Goldies, Diamond Lil, which just so happen to be five minutes from my apartment! Union Pool is always a good time on Saturdays and they have an amazing taco truck which is perfect for a late night snack. I also like going to Kinfolk 90/Kinfolk 94, the music and crowd is always a vibe!


Minami Gessel, Editor at Glossier 

Precisely how many layers are involved in your winter ‘going out’ outfit?

Because I live in Los Angeles, I have only have one! Just a jacket and an Alexander Wang x Uniqlo heattech bodysuit!

Why is this your ‘going out’ look?

It’s comfortable and chic. The pants are thick so they’ll keep me warm but are flowy so I can eat a nice meal without unbuttoning them after. The dad shoes are great for stomping around in and it’s leather so my feet won’t get wet if it rains.

How would you describe your winter ‘going out’ philosophy?

Keep a warm jacket with me and a cute outfit underneath because I know I’m going to get hot.

What’s the ‘going out’ spot that is most likely to get you out of your home?

Most likely ramen or soonduboo soup. The best ramen is Shin-sen-gumi in Gardena! There’s always a line but honestly it’s worth the wait.

Get more Fashion ?