Fashion

Here’s How to Style Leggings on Days You Can’t Deal With Jeans

written by TINSLEY CRISP

The Everygirl’s product selections are curated by the editorial team. If you buy something through our links, we may earn an affiliate commission, at no cost to you. We only recommend products we genuinely love.

"
Source: @laura.byrnes
Source: @laura.byrnes

It’s hard to imagine a world without leggings being incorporated into our everyday wardrobes. You’d be hard-pressed to find someone without a pair of black leggings (or two, or three…) in their closet waiting to be reached for on off days. But the style evolution of leggings has made them go from the no-brainer, off-duty pants of choice to a bottom that now feels a bit… lackluster. In an effort to breathe new life into the closet mainstay, I set out to find elevated ways to style them that make them feel exciting to reach for again.

Perhaps it was the two years of most of us being bound to our homes that finally did it, but the current consensus of fashion seems to be that many people—myself included—are ready to exit the era of overly casual style. While I personally have started reserving my leggings for the gym and reaching for comfortable alternatives instead, the leggings of 2025 have finally gotten the upgrade they’ve long deserved. 

With a range of more elevated styles on the scene—from flare versions to stir-up adorned pairs—leggings are fighting to be a mainstay in your winter closet, and these six outfits prove it.

6 Elevated Ways to Style Leggings This Winter

1. With Flats and a Blazer

Stirrup leggings—a style passed down from the ‘80s—are making headlines as this season’s it-girl item. My guess is that the trend was influenced by—you guessed it—a desire for more elevated leggings options. Here, the band underneath the arch of the foot helps to bridge the gap between the hem of the pant and the feet, resulting in a more seamless effect. This look is largely centered around the ballet flats, a more elevated footwear choice than say, a pair of sneakers or booties. Completed with a long, oversized blazer, you definitely won’t be mistaken for having just left a workout in this outfit.

Tailored Blazer
DISSH
Tailored Blazer
Shop now
Fleece-Lined Stirrup Leggings
Old Navy
Fleece-Lined Stirrup Leggings

3 colors available

Shop now
Mary Jane Flats
Madewell
Mary Jane Flats

3 colors available

Shop now
Wind Gold Earrings
Heaven Mayhem
Wind Gold Earrings

2 colors available

Shop now

2. With a Quilted Jacket and Chunky Scarf

If you needed proof that leggings don’t have to look like they’re a part of your SoulCycle uniform, here it is. By opting for a smaller bag rather than a tote and reaching for boots instead of sneakers, this outfit becomes an easy-yet-stylish look for a brisk morning walk or a coffee shop hang. While the roomy coat could easily star as the outfit’s headliner, the complimenting cold-weather accessories add texture and color that solidify themselves as the look’s focal point.

Quilted Liner Jacket
Everlane
Quilted Liner Jacket

5 colors available

Shop now
Chunky Plaid Scarf
Free People
Chunky Plaid Scarf

5 colors available

Shop now
Marled Yarn Beanie
J.Crew
Marled Yarn Beanie

3 colors available

Shop now
Platform Booties
Steve Madden
Platform Booties

2 colors available

Shop now

3. With Loafers and a Trench Coat

Source: @trendingwithtinsley


My cold-weather style is abysmal without my carefully curated assortment of outerwear. Come winter, my coat is my outfit, so on the days when I can’t be bothered to figure out the rest, I know that I can wholly rely on a pair of leggings to complete the look. The trick to looking more put together? It’s all about the accessories: statement footwear, rich layers, and staple jewelry.

Brushed Cashmere Cardigan
J.Crew
Brushed Cashmere Cardigan

3 colors available

Shop now
Trench Coat
Abercrombie & Fitch
Trench Coat

2 colors available

Shop now
High-Rise Leggings
Athleta
High-Rise Leggings

12 colors available

Shop now
Leopard Penny Loafers
Steve Madden
Leopard Penny Loafers

10 colors available

Shop now

4. With Sneakers and a Button-Down

Thanks to the blazer and button-up top, it initially didn’t even register to me that this look included leggings. Her more casual bottom-half, complete with ribbed socks and chunky sneakers, is balanced with more structured styling up top, making the outfit more office-ready than gym-ready. Complete with a few statement accessories? BRB—filing under “outfits I can’t wait to wear.”

Oversized Denim Shirt
Quince
Oversized Denim Shirt

3 colors available

Shop now
Double-Breasted Blazer
Old Navy
Double-Breasted Blazer

2 colors available

Shop now
Leather Bucket Tote Bag
Madewell
Leather Bucket Tote Bag

3 colors available

Shop now
9060 Sneakers
New Balance
9060 Sneakers
Shop now

5. With Boots and a Sweater

A decade of casual legging styling has made my brain associate them exclusively with sneakers and completely forget they can be paired with my knee-high boots instead. This outfit has reminded me to pair my leggings with my favorite chunky sweater, a statement-making layer, and go-to knee-high boots ASAP.

Oversized Cable-Knit Sweater
J.Crew
Oversized Cable-Knit Sweater
Shop now
Leather Shearling Bomber Jacket
Banana Republic Factory
Leather Shearling Bomber Jacket
Shop now
Black Leather Boots
Steve Madden
Black Leather Boots

2 colors available

Shop now
Oval Sunglasses
Le Specs
Oval Sunglasses
Shop now

6. With a Fur Coat and Statement Bag

At this point, you’re probably starting to pick up on the fact that when it comes to styling a pair of leggings, outerwear makes all the difference. And if you’ve spent any time online this season, then you’ve probably also noticed an influx of fur coats on your For You page. Perhaps what makes the item so covetable is the idea that it gives us one more texture to play with for the season—one that can become pretty repetitive, style-wise—and that it looks insanely good against a luxe leather bag.

Faux-Fur Coat
Urban Outfitters
Faux-Fur Coat
Shop now
Faux-Fur Coat
Abercrombie & Fitch
Faux-Fur Coat

3 colors available

Shop now
Quilted Crossbody Wristlet
Coach
Quilted Crossbody Wristlet

10 colors available

Shop now
Italian Leather Shoulder Bag
J.Crew
Italian Leather Shoulder Bag
Shop now

Shop Our Favorite Leggings

Ponte Stirrup Leggings
Madewell
Ponte Stirrup Leggings
Shop now
Fleece-Lined Leggings
Plush
Fleece-Lined Leggings
Shop now
Full-Length Leggings
Spanx
Full-Length Leggings
Shop now
Align High-Rise Leggings
Lululemon
Align High-Rise Leggings
Shop now
Everyday Soft High-Rise Leggings
All in Motion
Everyday Soft High-Rise Leggings
Shop now
Full-Length Leggings
GAP
Full-Length Leggings
Shop now
High-Rise Flare Leggings
GAP
High-Rise Flare Leggings
Shop now
Stretch Knit Split-Hem Leggings
Lululemon
Stretch Knit Split-Hem Leggings
Shop now
Plus Flex Flare Leggings
Madewell
Plus Flex Flare Leggings
Shop now
Perform 24/7 Leggings
Everlane
Perform 24/7 Leggings
Shop now
tinsley crisp
ABOUT THE AUTHOR

Tinsley Crisp, Fashion & Beauty Staff Writer

Tinsley Crisp is a Fashion & Beauty Staff Writer at The Everygirl and specializes in reporting on the season’s latest trends and hottest products. As a New York City-based stylist, she’s committed to injecting joy into the art of getting dressed and delivering attainable yet aspirational content to our readers.