9 Winter Outfits to Keep You Looking Cool All Season

As we enter the holiday season, let’s have a little refresher on how to elevate our basic winter style, shall we? We took inspiration from today’s It-girls like Bella Hadid and Zendaya as well as the hottest runway shows to give you the best foundation for your cold-weather looks. It’s easy to cling to the safety of those all-black outfits, but now, it’s time to venture outside of your comfort zone. From smile-inducing sweaters and animal prints to furry accessories worn by Rihanna, there are plenty of ways to brighten up your winter outfits this season.

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 colder temperatures. We often feel the chilly months mean we have to hide our fashion-forward sides under our puffer coats and thick ankle boots for the snow. Nevertheless, incorporating these statement styles will make sure you don’t miss a beat when it comes to your street style.

Scroll on for 10 cute winter outfit ideas that will serve as inspiration throughout the chilly months ahead.

Platform Boots

elsa hosk nyc street style gray skirt and ugg boots


Platforms are back with a vengeance and are making no plans to leave again. This time around the 2022 shoe trend has 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

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High Waisted Ruched Side Midi Skirt

Express High Waisted Ruched Side Midi Skirt

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Moto Jackets

hailey bieber street style leather jacket and cargo pants

Pierre Suu

The best moto jackets have proven themselves a timeless staple. The zipper details, ribbed padding, and shoulder pads give you that extra power to take on these 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 wore in middle school (that we also had in a million different colors and prints)? Well, the plaids may be gone, but the Bermuda shorts are becoming a must-have for a chic schoolboy look. Pair them with tights, knee socks, or knee-high boots to beat any wind chills.

Twill Shirt Jacket

Banana Republic Twill Shirt Jacket

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Dillon Bermuda Short

Nili Lotan Dillon Bermuda Short

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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 outfits are the easiest choice for the cold months ahead, and black and neutrals are usually what come to mind. Think outside the box this season and flaunt neon from head to toe. After all, 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

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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 the 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 for maximum warmth. Your outfits will still feel and look like your own personal style, just with 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

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Animal Print Mania

16arlington springsummer 2023

Kate Green/BFC//Getty Images

Animal prints were once a bold fashion choice, but lately, we have been spotting this trend down the runway—and even on our sidewalks. If you aren’t ready to rock a head-to-toe look à la Shania Twain, search for the right animal print for you and start with one clothing item. You’ll soon discover that this is just what you need to take 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 eye-catching knit with trousers and bold-colored shoes for a head-turning 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

preview for Jenna Ortega | First Thing With

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