15 Holiday Legging Outfits to Wear When Comfort Is the Priority
When you think about holiday parties, you might automatically think about glitz and glamour courtesy of pretty dresses, stunning shoes, and sparkly accessories. One item that never comes to mind (at least not at first) is leggings. Sure, maybe they make a brief cameo in the moments before you head out to the party, when you're lounging in your room figuring what to wear, or after your holiday party when you're already taking off all your makeup. Regardless, one thing we know for sure is that somehow leggings are never a part of your actual party outfit. This year though, it's time to change that. It’s time leggings join the party—literally.
No, we're not saying to give up on everything in life and simply wear boring leggings to all your holiday outings. What we want you to do is approach this ultra-comfortable garment with open arms and curiosity. Let’s give them a chance because deep down we all love a good fitted legging. They have become our go-to pair of pants when it comes to traveling and relaxing, so now it’s time to make our holiday outfits stand out while wearing this problematic fave garment.
To find all the inspiration we need to see leggings in a whole new light, we've rounded up 15 holiday outfits with leggings that don't sacrifice one bit of style.
When we talk about stylish comfort, we envision this outfit.
Patent leather leggings are a thing, and you should give them a try.
Pair your leather leggings with your leather jacket for the ultimate stylish combo.
Proof that your oversize turtleneck goes with everything (even your leggings).
How chic!
A dress over leggings is a classic styling combo you shouldn't take for granted.
Pro tip: Match your boots to your blazer.
Not 100% leggings, but still just as comfortable.
Simply spending time with your family? This outfit is for you.
Black and white is a color combo that can't be beaten.
Your over-the-knee boots look (and fit) best when paired with leggings.
Talk about a stylish and comfortable look.
Jeggings can even work for your Canadian tuxedo.
Stay warm by pairing your monochrome outfit with a trusted puffer.
Proof that leggings and glitter boots look great together.
More legging outfits FTW.
-
Forget Fleeces and Hoodies—This Is the It-Girl Jacket to Wear With Plain Leggings
It's taken over by storm.
-
5 Street Style Trends From Milan Fashion Week That Will Be Everywhere This Fall
Take notes.
-
If You're Going to Wear Leggings in Fall 2025, Wear Them in This Shade With White Sneakers
As spotted on Jennifer Lopez in NYC.
-
Black Leggings Are Fine, But It Girls Know These 6 Trendier Versions Feel So Now
They're so much cooler.
-
Yes, Fashion People Are Still Wearing Leggings, But Only This Specific Style (and Not With Sneakers)
The comfy-chic pairing we spot on every L.A. and New York It girl.
-
Legging Season Is Here—These Are the 7 Trends Everyone Everywhere Will Be Wearing
A fresh take.
-
Cooler Than Leggings—Everyone With Good Taste Is Wearing This Casual Outfit Combo This Fall
Count us in.
-
This Dated Denim Pairing Is Suddenly the Chicest Way to Wear Jeans for Fall 2025
Easy and stylish.