Brit + Co Logo

Tips for your best (and comfiest) 'fits.

How To Style Leggings For Winter (& Not Look So Millennial)

How To Style Leggings
Leah Newhouse / PEXELS

Trends will come and go, but I will always be a leggings girly through and through. Not only do I love their versatility, they also tend to make my legs look fantastic. The only problem with leggings is I often get overwhelmed over how to properly style them since there are so many different options to choose from. Plus, I want to make sure I’m styling mine for the 2020s, not the 2000s.

If you’re hoping to spend the entirety of the holiday season in a pair of leggings, you’re in good company. Leggings are totally back in style right now, so no one will shame you for looking like a #Millennial... as long as you style them the right way. If you feel overwhelmed by all the styling options, you’ve come to the right place.


Here are my 5 favorite ways to rock leggings during winter.

High-Waist Leggings + Cropped Sweater

Cottonbro Studio / PEXELS

High-Waist Leggings + Cropped Sweater

This is one of my favorite looks of all time. It’s so 90s, which I’m all about, yet it’s also very modern. You know what they say, what’s old is new again! This combo is the perfect blend of casual and chic.

Black Leggings + Oversized Graphic Sweater

Karola G / PEXELS

Black Leggings + Oversized Graphic Sweater

I love this combo because it offers a touch of personality. The oversized graphic sweater shows the world you’ve got character, whether it displays a pattern of your favorite ‘90s cartoon characters or a funny statement that’ll have passersby chuckling at the cleverness. Meanwhile, the simple black leggings let the graphic sweater take center stage while still adding an attractive silhouette that looks amazing on all body types.

Patterned Leggings + Monochromatic Top

Wesley Davi / PEXELS

Patterned Leggings + Monochromatic Top

Sometimes, you just want your leggings to be the main accessory, and I’m all for this kind of look as well. Heavily patterned leggings instantly remind me of Fran Drescher's character on The Nanny, who often wears patterned bottoms with a monochromatic top (usually solid black). Who in their right mind wouldn’t want to style themselves like Fran Fine?

Neon Leggings + Solid Black Top

Leeloo The First / PEXELS

Neon Leggings + Solid Black Top

Here’s another look I adore, which fuses eccentric edge with classic practicality. Put them together, and it creates an unforgettable look that’ll have you receiving compliments from left to right. Bonus points if you add a signature pair of hoop earrings to complete the fun look.

Black Leggings + Black Top + Signature Boots

Leah Newhouse / PEXELS

Black Leggings + Black Top + Signature Boots

Simple black leggings have a habit of making your shoes look extra cute, since your footwear will stand out more against the tight black fit. That’s why I love showing off my absolute favorite winter boots with my all-black outfit, so the shoes themselves stand out. Grab your favorite pair of winter boots or high heels, so they can finally have their main character moment.

Subscribe to our newsletter for more style advice!

EXPLORE MORE OF BRIT + CO

Selfmade

Selfmade

A business accelerator for early-stage female founders with live workshops, 1:1 mentoring, online courses, and curated business support. Visit

B+C Newsletter

Subscribe to B+C

Get your weekly dose of inspo, pop culture, and creativity — straight to your inbox. Subscribe to the Brit + Co newsletter! Visit