Dressing Like a Cool Girl This Winter

Master effortless winter style with elevated basics and timeless pieces.

POSTED BY JORDYN ROSEN

Winter Fashion is a completely different playing field than summer. Summer is cute, flirty, and fun outfits, but winter – that’s when the cool girls' outfits thrive. The trendy pieces from your summer wardrobe suddenly don’t cut it, and what’s left feels like a personality test. Dressing for the cool seasons isn’t just about staying warm; it’s about embracing a whole new aesthetic.

Last winter, I lived in a beach town, where it did get all four seasons and snow, but winter fashion wasn’t the vibe. It’s like Belly, from The Summer I Turned Pretty, once said, “For me, it was almost like winter didn’t count. Summer was what mattered.” Moving to London – AKA a city that thrives despite the weather – I knew it was time to step up my game.

My favorite part about building my cool-girl winter closet (besides the excuse to buy new clothes, of course) is curating my closet to make me feel like the main character. I’ve been rewatching Friends recently, and you can bet I’m copying Monica's outfits. She always looks put together without trying too hard. When building your own winter wardrobe, take a page from Monica: invest in classic staples that can be layered in different ways, mix textures like wool, leather, and faux fur. Don’t be afraid to play with proportions – think oversized sweaters with fitted bottoms or long coats with chunky scarves.

I’ve found that the key to dressing like a cool girl in winter isn’t about copying a specific aesthetic, it’s about taking inspiration from what feels the most you. Loving your closet makes winter feel cool and exciting instead of dreadful. For me, loving my closet involved stealing some pieces from Monica's.

And if you’re ready to build your own winter main character wardrobe, dive into our Fizzypicks — the cozy staples and cool-girl essentials we’re actually loving this season:

L'AGENCE
Kaisley Tweed Single-Breasted Blazer
$750

 

CINQ Á SEPT
Saule Blazer Minidress
$595

 

CINQ Á SEPT
Cheyenne Sequin-Embellished Floral-Embroidered Scrunched Blazer
$417

 

H&M
Shirt
$19.99

 

H&M
Fine-Knit Cardigan
$11.99

 

H&M
Ava Ultra High Rise Wide Leg Jeans
$29.99

 

PRINCESS POLLY
Anse Sleeveless Minidress
$45

 

OPEN EDIT
Ruched Side Top
$39.50

 

OPEN EDIT
The Icon A-Line Miniskirt
$49.50

 

ASTR THE LABEL
Chantel Plaid Pleated Miniskirt
$128

 

URBAN OUTFITTERS
BDG Kayla Destructed Low-Rise Jean
$75.00

 

URBAN OUTFITTERS
BDG River Oversized Cropped Turtleneck Sweater
$34.30

 

ACNE STUDIOS
Hooded Zip-Up Sweatshirt
$850

 

ACNE STUDIOS
Fitted Wool Vest
$580

 

ACNE STUDIOS
Mohair Cardigan
$900

 

GARAGE
Sleek V-Neck Long Sleeve Top
$34.95

 

GARAGE
Estelle Longline Tee
$26.95

 

GARAGE
Shirred Low Back Halter Top
$36.95

 

POLO RALPH LAUREN
Knit Turtleneck Midi-Dress
$298

 

TOCCIN
Lena Turtleneck Minidress

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