Leggings in winter? Absolutely! Gone are the days when these comfy stretchy pants were relegated to just gym wear. Now, they’re a versatile staple that can take you from cozy nights in to stylish nights out. As someone who practically lives in leggings during the colder months, I’ve teamed up with some fashion-forward friends to bring you 15 chic ways to rock your leggings this winter. Trust me, your legs (and your style cred) will thank you.
Oversized Sweater and Ankle Boots
Saodimallsu Sweater VIEW ON AMAZON
luvamia Legging VIEW ON AMAZON
Columbia Pom Beanie VIEW ON AMAZON
Who says comfort can’t be chic? Pair your favorite leggings with an oversized sweater that’s basically a wearable hug.
Add some ankle boots, and you’re ready to conquer the world (or at least the coffee shop). This look screams “I woke up like this” but in the best way possible.
Pro tip: Play with textures! A cable-knit sweater adds visual interest and keeps things from looking too plain.
Leather Jacket and Combat Boots
Athlemo Biker Coat VIEW ON AMAZON
Lauren Ralph Lauren Skinny Ankle Jeans VIEW ON AMAZON
Sorel Boot VIEW ON AMAZON
Channel your inner rock star with this edgy ensemble. Black leggings + white tee + leather jacket = instant cool.
Throw on some combat boots, and you’re ready to take on whatever the day throws at you. Maybe even start a band. Who knows?
For extra punk points, add some studded accessories. Just don’t go overboard, or you might set off metal detectors.
Tunic Dress and Knee-High Boots
Balance Collection Legging VIEW ON AMAZON
Vepose Boot VIEW ON AMAZON
Long live the leggings-as-pants debate! This outfit cleverly sidesteps the issue altogether.
A flowy tunic dress over leggings is like having your cake and eating it too – comfy and stylish. Add knee-high boots for that perfect autumn vibe.
Bonus: This combo works great for those “I ate too much at Thanksgiving” days. Not that I’m speaking from experience or anything.
Plaid Shirt and Sneakers
Gary Com Jackets VIEW ON AMAZON
SATINA Leggings VIEW ON AMAZON
Tommy Hilfiger Sneaker VIEW ON AMAZON
Embrace your inner lumberjack (but make it fashion) with this cozy-casual look. An oversized plaid shirt paired with leggings is the ultimate weekend warrior outfit.
Slip on some sneakers, and you’re ready for anything from a forest hike to a Netflix marathon. Don’t forget a beanie for extra warmth and style points!
Faux Fur Vest and Riding Boots
Willit Legging VIEW ON AMAZON
Style Republic Chunky Knit Beanie VIEW ON AMAZON
Who says you can’t be glamorous and practical? This outfit says “I’m ready for a winter wonderland photoshoot” while still keeping you toasty.
The faux fur vest adds a touch of luxury, while riding boots keep things grounded (literally). Perfect for those “let’s go cut down our own Christmas tree” adventures.
Denim Shirt and Loafers
PJ PAUL JONES Denim Blouse VIEW ON AMAZON
HUE Leggings VIEW ON AMAZON
Ruiee Combat Boot VIEW ON AMAZON
Sometimes, simple is best. A classic denim shirt paired with black leggings is like the PB&J of outfits – it just works.
Add some loafers for a preppy twist, and you’re ready for a day of running errands or hitting the books. It’s the perfect “I tried, but not too hard” look.
Chunky Cardigan and Moccasins
Verdusa Sweater VIEW ON AMAZON
90 Degree By Reflex Leggings VIEW ON AMAZON
Minnetonka Moccasin VIEW ON AMAZON
If “hygge” were an outfit, this would be it. Wrap yourself in a chunky cardigan, slip on some cozy moccasins, and you’re ready for a day of serious lounging.
Or, you know, adulting if you must. The best part? You’ll look put-together even if you’re just heading to the mailbox.
Long Blazer and Heeled Ankle Boots
KIRUNDO Long Blazer VIEW ON AMAZON
Who says leggings can’t be office-appropriate? Pair them with a crisp white blouse and a long blazer for instant boss-lady vibes.
Heeled ankle boots add a touch of sophistication. Warning: This outfit may cause sudden urges to lean on things and look pensively into the distance.
Poncho and Wedge Boots
Lion Brand Yarn Mandala VIEW ON AMAZON
NexiEpoch Legging VIEW ON AMAZON
DOEYG Heel VIEW ON AMAZON
Embrace your inner fashionable nomad with this boho-chic ensemble. A colorful poncho adds instant style to simple leggings.
Wedge boots give you a little height without sacrificing comfort. Perfect for those “I’m a free spirit, but I also have errands to run” days.
Turtleneck and Over-the-Knee Boots
FISACE Sweater VIEW ON AMAZON
DREAM PAIRS Boot VIEW ON AMAZON
Channel your inner Audrey Hepburn with this sleek and sophisticated look. A turtleneck and leggings combo is timeless, but add some over-the-knee boots and suddenly you’re ready for the runway.
Or at least the grocery store runway. Remember, confidence is key – strut like you mean it!
Flannel Shirt and Ugg Boots
EVALESS Shacket VIEW ON AMAZON
BOOPH Legging VIEW ON AMAZON
WFL Boot VIEW ON AMAZON
Embrace the classic “basic” look, but make it fashion. A cozy flannel shirt paired with leggings is the ultimate in comfort.
Add some Ugg boots (don’t pretend you don’t have a pair), and you’re ready for a day of pumpkin spice lattes and hayrides. Basic? Maybe. Comfortable? Absolutely.
Sweater Dress and Thigh-High Socks
YKR Sweater VIEW ON AMAZON
RUIXIB Legging VIEW ON AMAZON
Style Republic Beanie VIEW ON AMAZON
For those days when you want to feel like a cozy, sexy librarian (it’s a thing, trust me). Layer a sweater dress over your leggings, add some thigh-high socks, and finish with ankle boots.
It’s like wearing a blanket, but make it fashion. Plus, those thigh-high socks are basically leg warmers for adults. Win-win!
Puffer Vest and Snow Boots
LONGKING Vest VIEW ON AMAZON
Conceited Legging VIEW ON AMAZON
THE NORTH FACE Pom Beanie VIEW ON AMAZON
Who says you can’t be stylish while building a snowman? Pair your leggings with a cozy thermal shirt and a puffer vest for a look that’s both practical and cute.
Snow boots keep your toes toasty. Warning: This outfit may lead to spontaneous snow angel making.
Belted Tunic and Ballet Flats
GRACE KARIN Jackets VIEW ON AMAZON
Conceited Leggings VIEW ON AMAZON
Mali+Lili Bag VIEW ON AMAZON
For when you want to feel put-together but can’t bear the thought of “real” pants. A long tunic belted at the waist creates a flattering silhouette, while ballet flats keep things elegant.
It’s the perfect outfit for pretending to understand modern art or sipping overpriced coffee. Culture, darling!
Hoodie and High-Top Sneakers
Sometimes, you just need to channel your inner teenager. An oversized hoodie paired with leggings is the ultimate in comfy-cool.
Add some high-top sneakers, and you’re ready to hit the skate park. Or, more realistically, the couch. Either way, you’ll look cool doing it.
There you have it, folks! Fifteen ways to rock your leggings this winter without looking like you’ve given up on life. Remember, fashion is all about having fun and expressing yourself. So go forth, be comfy, and conquer the world – one stretchy pant leg at a time!
