What to Wear When It’s Cold and You Still Want to Look Cute

Photo Credit:@georgiaebayliss

Cold weather has a way of making us want to choose warmth over style — but who says you can’t have both? The right winter pieces can keep you cozy without sacrificing an ounce of cute. Whether you’re walking to work, hitting the holiday market, or braving the cold for brunch, these 20 outfit ideas prove that bundling up doesn’t mean hiding your style. We’re talking flattering layers, smart accessories, and coats that actually complement what’s underneath.

Before you start adding to cart, grab my free Holiday Gift Tracker Spreadsheet — it keeps all your ideas, budgets, and “already bought” list in one place so nothing (and no one) slips through the cracks.

When You Want Your Coat to Be the Main Event

Amazon

Cropped Pea Coat

$39.99

Amazon

Textured Faux Leather Jacket

$39.99

BLANKNYC Midnight Run Jacket

Midnight Run Jacket

$188.00

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For the Morning Commute That Feels Like the Arctic

A.L.C. Bria Coat

Bria Coat

$895.00

STAUD Wally Boots

Wally Boots

$495.00

Citizens of Humanity Miro Relaxed Jeans

Miro Relaxed Jeans

$268.00

When You Need Layers That Don’t Add Bulk

Amazon

Light Weight Sweater Top

$32.99

Amazon

Cuffed Baggy Jeans

$36.99

Amazon

Chunky Mid Heel Booties

$59.99

For a Date Night That Requires Walking Outside

Petal & Pup Women's Callum Midi Dress

$89.00

Amazon

Over Knee High Boots

$74.36

Amazon

Mini Crossbody Bag

$37.77

When You Want to Wear a Skirt Without Freezing

ESSENTIEL ANTWERP Faux Fur Jacket

Faux Fur Jacket

$505.00

STAUD Wally Boots

Wally Boots

$495.00

A.L.C. Conan Skirt

Conan Skirt

$395.00

For Outdoor Holiday Markets and Light Displays

Chunky Knit Jumper

$34.99

Oversized Long Sleeve Fall Sweater

$29.99

When You Need Boots That Actually Keep Your Feet Warm

Sam Edelman Laguna Boots

Laguna Boots

$160.00

FERRAGAMO Kisty Boots

Kisty Boots

$1,250.00

For the Outfit That Goes Straight From Outside to Inside Comfortably

Line & Dot Hart Sweater

Hart Sweater

$102.00

Line & Dot Hart Sweater Skirt

Hart Sweater Skirt

$99.00

Half Zip Sweatshirts And Wide Leg Pants

$48.99

When You Want to Wear Color in a Sea of Black Coats

Damson Madder Pearl Puffer Jacket

Pearl Puffer Jacket

$240.00

For the Days You Need to Wear Your Warmest Sweater

Avec Les Filles Oversized Maxi Combo Trench Coat

Oversized Maxi Combo Trench Coat

$198.00

When You Need an Outfit That Photographs Well in the Snow

ESCVDO Musa Long Sleeve Maxi Dress

Musa Long Sleeve Maxi Dress

$1,300.00

Flare Ribbed Short Dress

$35.99

For Brunch on the Patio With Heat Lamps

Sweater Lounge Set

$48.97

Citizens of Humanity Odette Puff Sleeve Pullover

Odette Puff Sleeve Pullover

$398.00

When You Want a Hat That Completes the Outfit

Janessa Leone Sherman Hat

Sherman Hat

$287.00

For the Winter Wedding Guest Look That Won’t Leave You Shivering

Formal Fall Wedding Guest Dress

$47.99

For more holiday outfits, gift ideas, and deals worth clicking, head to the Autum Love Holiday Hub. Bookmark it now — I’m adding fresh finds all season.