13 Winter Fashion Styles for Cold Weather, From $20

Baby, it’s cold outside. I’m coming up on my third winter as a NYC resident, and I lived in Boston for four years prior, so I’m schooled in the art of bundling up. The time has finally come again to brave wind tunnels, slushy sidewalks, and the dreary gray December days—but not without my arsenal of reliable winter gear.

I’m the type who will forgo a jacket if it means showing off an outfit, but I simply can’t suffer for my fashion anymore in this frigid air. So, instead, I turn to fancy puffer jackets, chic loungewear, weather-appropriate boots, and elevated basics to get me through the season in style. My cool-girl winter capsule wardrobe consists of items I can remix for all my outings, from bodega runs to office days, date nights, and everything in between.  

Scroll below to shop 13 essentials from $20 you’ll keep in rotation through early spring.

13 Best Cool-Girl Winter Staples

• Not-Basic Puffer: Free People Printed Cotton Candy Puffer, $228; freepeople.com 
• 24/7 Cozy Staple: Automet Two-Piece Sweatsuit, $60 (Originally $70); amazon.com
• Winter Essential: Ugg Classic Ultra Mini Platform Boot, $160; nordstrom.com
• Maeve Brushed Icon Scarf, $41 (Originally $58); anthropologie.com 
• Celeb-Approved: Free People Hit The Slopes Fleece Jacket, $148; freepeople.com
• Fixmatti Fuzzy Three-Piece Lounge Set, $55; amazon.com 
• Sam Edelman Lyla Knee High Boot, $140 (Originally $200); nordstrom.com 
• Most Versatile: Zesica Thermal Long Sleeve Mock Neck Top, $20 (Originally $25); amazon.com
• 60%-Off Deal: Everlane The Puffer Bomber, $91 (Originally $228); everlane.com
• Dr. Martens 2976 Leonore Chelsea Boot, $115 (Originally $180); amazon.com
• J.Crew Leather Gloves, $23 (Originally $80); jcrewfactory.com 
• Levi’s Faux Shearling Lined Faux Leather Moto Jacket, $130 (Originally $225); nordstrom.com 
• Free People Smitten Faux Fur Earmuffs, $48; freepeople.com

Free People Printed Cotton Candy Puffer

First things first—a puffer coat is non-negotiable. Opt for a heavy duty, investment-worthy style like this one from Free People, which features a durable nylon shell and plush insulation. The gingham pattern and tie cuffs are so cute, and the colors will breathe a little life into even the dullest days of winter.  

Automet Two-Piece Sweatsuit

I just placed my order for Automet’s two-piece sweatsuit in this trending espresso color. I love sets like this because I can wear them while I work from home, lounge around the house, or trek to a workout class (layered over my workout gear) while still feeling somewhat put together. Shoppers say the “material is thick and cozy” and “perfect for colder winter days.” And marked down too? Score.

Ugg Classic Ultra Mini Platform Boot

It’s not winter without a pair of classic Ugg boots. This platform silhouette has a significant 2.25-inch height boost (ideal for petite gals like me), a fuzzy and moisture-wicking wool-blend lining, and a shorter shaft that leaves room for styling with slouchy socks or leg warmers. 

Maeve Brushed Icon Scarf

A blanket scarf will take you far on bitterly cold days, whether you wear it as a shawl, tie it like a hood, or completely cocoon your neck and shoulders. This bow-printed scarf from Anthropologie offers a cute accent to any outerwear ensemble, with a two-tone reversible design in pink or brown color options. 

Free People Hit The Slopes Fleece Jacket

Free People’s Hit The Slopes Fleece Jacket stays on rotation in the wardrobes of Kaia Gerber and Hailey Bieber. Available in 19 bold and neutral color options, this lightweight yet ultra-warm jacket is a great topper on its own, or a substantial layering piece in below-freezing temps. It features a snap-button closure, zipper pockets, and a comfy relaxed fit. 

Fixmatti Fuzzy Three-Piece Lounge Set

This warm and fuzzy lounge set is what winter dreams are made of. It comes with a crop tank, pants, and a long cardigan in a plush fabric that “feels like a blanket,” according to one shopper. Wear the whole set as a monochromatic ‘fit for movie night or chilling with the girls, or mix and match each piece with other items in your closet. 

Sam Edelman Lyla Knee High Boot

Knee-high boots are a no-brainer in cold weather, because they offer the polish of the heel with extra warmth from the extended shaft. Sam Edelman’s Lyla Knee High Boots are on sale for $60 less right now, and feature stylish details like shiny hardware, square toes, and flared kitten heels for easy-walking. 

Zesica Thermal Long Sleeve Mock Neck Top

Boy, do I love a black turtleneck, and this Zesica style ups the ante with thermal insulation. Layer it under tees, sweaters, and crewneck sweatshirts, or style it as a top with jeans, mini skirts, and trousers—it’s the most versatile outfit building block to have on hand. 

Below, shop more stylish winter must-haves, including a 60 percent off Everlane puffer, discounted shearling-lined Dr. Martens Boots, and tech-friendly leather gloves.

Everlane The Puffer Bomber

Dr. Martens 2976 Leonore Chelsea Boot

J.Crew Leather Gloves

Levi’s Faux Shearling Lined Faux Leather Moto Jacket

Free People Smitten Faux Fur Earmuffs