9 Winter Outfits to Keep You Looking Cool All Season

Fashion

As we enter the winter season, let’s have a little refresher on how to elevate our basic winter style. We took inspiration from today’s IT-girls like Bella Hadid and Zendaya and the hottest runway shows to give you the best foundation for your winter looks. There will be no more clinging to the safety of those all black outfits; time to live in color. These pieces are the hottest and most essential needed to brave the cold. From smile-inducing sweaters, furry accessories worn by Rihanna, and animal prints, there’s plenty of options to keep your wardrobe in rotation.

Don’t be afraid to bust out those favorite summer pieces in your closets. We’ll show you how to winterize those shorts and sandals to keep you feeling and looking hot in the cool temperatures. We often feel the chilly months mean we have to hide our fashion-forward under our puffer coats and thick snow boots. Nevertheless, incorporating these statement styles will make sure you don’t miss a beat when it comes to your street style.

Look below for 10 warm winter outfits that will serve as major inspiration throughout the chilly months ahead.


Platform Boots

elsa hosk nyc street style gray skirt and ugg boots

Rachpoot/Bauer-Griffin

Platforms are back with a vengeance and are making no plans to leave again. This time around platforms have taken on the iconic y2k Ugg boot. Step out in this redesigned classic to take your winter wardrobe to new heights.

Classic Mini Platform Boot

UGG Classic Mini Platform Boot

Ultra Soft Balloon Sleeve Duster

Express Ultra Soft Balloon Sleeve Duster

Now 73% Off

High Waisted Ruched Side Midi Skirt

Express High Waisted Ruched Side Midi Skirt

Now 56% Off


Moto Jackets

hailey bieber street style leather jacket and cargo pants

Pierre Suu

Leather motorcycle jackets have proven themselves to never be outdated. The zipper details, ribbed padding, and shoulder pads give you that extra power to take on these New York City streets. Be a babe and a total badass!

Jylan Leather Moto Jacket

Veronica Beard Jylan Leather Moto Jacket

Union Cargo Pants

Rumored Union Cargo Pants

Fink Studded Knee Boots

Steve Madden Fink Studded Knee Boots

Bermuda Shorts

bella hadid paris fashion week ss23 brown short suit

Marc Piasecki

Remember those bermuda shorts we used to wear in middle school that we had in a million different colors and prints? Well gone are the plaid prints, but the bermuda shorts are becoming a must-have this season for a chic schoolboy look. Pair them with tights, knee socks, or knee boots to beat any wind chills.

Twill Shirt Jacket

Banana Republic Twill Shirt Jacket

Now 60% Off

Dillon Bermuda Short

Nili Lotan Dillon Bermuda Short

Now 40% Off

Cener Knee Boot

Isabel Marant Cener Knee Boot

Fur Bucket Hats

rihanna nyc street style fur bucket hat

Pierre Suu

It’s ugly and outdated until Rihanna says it’s not. This furry accessory is impractical, weird, and just what you need to slay the day. Who cares about practicality when you’re turning heads? Added bonus if you get your favorite color in faux fur.

Faux Fur Bucket Hat

Tyler Lambert Faux Fur Bucket Hat

Birdie Denim Shirt in Kirk

Khaite Birdie Denim Shirt in Kirk

Island Mini Bowl Bag

Binge Knitting Island Mini Bowl Bag

Bold Color

zendaya valentino ss23 fashion week pink

Arnold Jerocki

Monochromatic is the easiest choice for the cold months ahead, but black and neutrals are what come to mind. Think outside the box and flaunt neon from head to toe. The 80s called and they want their colors back, but they won’t be getting them anytime soon.

Italian Wool Double-Breasted Coat

Karen Millen Italian Wool Double-Breasted Coat

Now 20% Off

Edie Satin Platforms

Jeffrey Campbell Edie Satin Platforms

Moor Leather Gloves

Agnelle Moor Leather Gloves

Puffer Coats

max mara fallwinter 2022

Andreas Rentz//Getty Images

One of my biggest dilemmas for winter dressing is finding something that feels warm, lightweight and breathable – the solution: a puffer coat. This winter closet staple is a must have for anyone who plans on surviving this winter season.

Ultra Puffer

The Super Puff™ Long

Artizia The Super Puff™ Long

No.188 Happy Roll-Neck Stretch-Cashmere Sweater

Extreme Cashmere No.188 Happy Roll-Neck Stretch-Cashmere Sweater

Balaclava Knit Hooded Turtleneck

Bevza Balaclava Knit Hooded Turtleneck

Socks with Sandals

fendi re23 runway show

Getty Images

Socks and sandals are the most interesting solution to spicing up your footwear game in the winter. Give your heels another life by pairing them with bright colored socks made in cashmere or wool material, for the maximum warmth. Your outfits will still feel and look like your own personal style, just more personality.

Socks with Sandals

Leila Satin Charmeuse Dress

BHLDN Leila Satin Charmeuse Dress

Bare Satin Asymmetrical Slingback Sandals

The Row Bare Satin Asymmetrical Slingback Sandals

On Sale

Cashmere & Wool-Blend Cozy Socks

Falke Cashmere & Wool-Blend Cozy Socks

Now 25% Off


Animal Print Mania

16arlington springsummer 2023

Kate Green/BFC//Getty Images

Animal prints were previously a bold fashion choice but we have lately been spotting this trend down the runway – and even on our sidewalks. If you aren’t ready to rock a head-to-toe look, search for the right animal print for you and start with one clothing item. You will soon discover that this is just what you need to push your outfits to the next level.

Animal Print Mania

Statement Sweaters

undercover springsummer 2022

Victor Virgile//Getty Images

If you’re looking to cure your winter blues, a statement sweater is just what you need. Pick a sweater that will fill you with joy whenever you read it because sometimes a cheesy saying is just what we need to lift our mood. Pair your statement sweater with trousers and bold colored shoes for a statement-making outfit.

Statement Sweaters

Gyles & George Women's "I'm a Luxury" Sweater

Rowing Blazers x Gyles & George Gyles & George Women’s “I’m a Luxury” Sweater

Dillon Virgin Wool Wide Leg Pants

Nili Lotan Dillon Virgin Wool Wide Leg Pants

Now 56% Off

Yellow Traktori Loafers

CamperLab Yellow Traktori Loafers

Now 50% Off

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