Fashion

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

written by TINSLEY CRISP

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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 2024 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.

leggings outfits
DISSH
Tailored Blazer
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leggings outfits
Old Navy
Fleece-Lined Stirrup Leggings

3 colors available

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leggings outfits
Madewell
Mary Jane Flats

3 colors available

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leggings outfits
Heaven Mayhem
Wind Gold Earrings

2 colors available

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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.

leggings outfits
Everlane
Quilted Liner Jacket

5 colors available

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leggings outfits
Free People
Chunky Plaid Scarf

5 colors available

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leggings outfits
J.Crew
Marled Yarn Beanie

3 colors available

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leggings outfits
Steve Madden
Platform Booties

2 colors available

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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.

leggings outfits
J.Crew
Brushed Cashmere Cardigan

3 colors available

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leggings outfits
Abercrombie & Fitch
Trench Coat

2 colors available

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leggings outfits
Athleta
High-Rise Leggings

12 colors available

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leggings outfits
Steve Madden
Leopard Penny Loafers

10 colors available

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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.”

leggings outfits
Quince
Oversized Denim Shirt

3 colors available

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leggings outfits
Old Navy
Double-Breasted Blazer

2 colors available

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leggings outfits
Madewell
Leather Bucket Tote Bag

3 colors available

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leggings outfits
New Balance
9060 Sneakers
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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.

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

2 colors available

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leggings outfits
Le Specs
Oval Sunglasses
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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.

leggings outfits
Urban Outfitters
Faux-Fur Coat
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leggings outfits
Abercrombie & Fitch
Faux-Fur Coat

3 colors available

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leggings outfits
Coach
Quilted Crossbody Wristlet

10 colors available

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leggings outfits
J.Crew
Italian Leather Shoulder Bag
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Shop Our Favorite Leggings

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