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

It’s hard to imagine a world where leggings don’t play a role in our everyday wardrobes. Most of us own at least one trusty black pair (if not two or three) permanently on standby for errands, travel days, and everything in between. But after years of nonstop wear, leggings have quietly shifted from a reliable go-to to something that can feel a bit… uninspired. In an effort to breathe new life into this longtime staple, I set out to find elevated ways to style leggings that actually feel exciting to reach for again.

If the past few years taught us anything, it’s that comfort isn’t going anywhere—but neither is our desire to look put-together. After an extended era of ultra-casual dressing, fashion has officially entered its refined comfort phase. Personally, I’d started reserving my leggings strictly for workouts, opting instead for polished alternatives that felt more intentional. But in 2025, leggings have undergone a subtle yet meaningful evolution—one that makes them feel worthy of a place back in our everyday rotation.

Today’s leggings are less about lounging and more about styling potential. From tailored flared silhouettes to sleek stirrup details and thicker, more substantial fabrics, the new wave of leggings feels thoughtful, directional, and surprisingly versatile. Styled the right way, they can hold their own alongside oversized coats, sharp boots, and elevated layers—especially in winter.

Ahead, six outfit ideas that prove leggings aren’t fading into the background just yet. With a few modern updates, they might just become one of the hardest-working pieces in your cold-weather wardrobe all over again.

6 Elevated Ways to Style Leggings This Winter

1. With a blazer and pointed flats

Stirrup leggings—a silhouette borrowed from the ’80s—have quickly become this season’s it-girl legging. The defining strap under the arch creates a seamless line from pant to shoe, instantly making the look feel more elevated. Styled with ballet flats and finished with a long, oversized blazer, they strike the perfect balance between comfort and polish—no chance of being mistaken for post-workout attire here.

H&M

Double-Breasted Blazer

4 colors available
sizes XXS – 4X

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SPANX

Ponte Stirrup Legging

2 colors available
sizes S – 3X

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Madewell

The Mylie Ballet Flats

5 colors available

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Heaven Mayhem

Wind Earrings

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2. With a quilted jacket and chunky scarf

If you needed proof that leggings don’t have to read as part of your SoulCycle uniform, this is it. Swapping a tote for a smaller bag and choosing boots over sneakers instantly elevates the look, making it perfect for a brisk morning walk or a casual coffee run. While the oversized coat holds its own as a statement piece, it’s the coordinating cold-weather accessories that add texture and color—ultimately stealing the spotlight.

Everlane

The Quilted Liner

5 colors available

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BohemianBoundaries | Etsy

Faux Mohair Scarf

3 colors available

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Quince

Italian Leather Shoulder Bag

4 colors available

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Steve Madden

Jones Boots

7 colors available

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3. With a triangle scarf and snow boots

Triangle scarves have quietly become the unsung heroes of winter dressing—serving as a chic alternative to a sweater draped over the shoulders, an easy pop of texture or color, and an extra layer of warmth all in one. What makes them especially worthy of investment is their versatility: wear one draped around the shoulders or tied over the head as a makeshift hat. Paired with a glossy puffer, aviator sunglasses, and snow boots, the result feels effortlessly après-ski—without the fuss.

S13

Kylie Glossy Puffer Jacket

2 colors available

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H&M

Garter-Stitched Triangle Scarf

2 colors available

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Cougar

Savvy Boots

2 colors available

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AIRE

Whirlpool Sunglasses

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4. With a trench coat and sneakers

You can absolutely keep things casual—after all, they’re still leggings—but adding structure with a statement trench coat and being intentional about your color palette makes all the difference. I love this look because it veers away from the typical all-black formula, offering a softer, more elevated take. Layer a polished white tee with a hoodie underneath for depth, then finish with a chunkier sneaker (my personal rule for slimmer leggings), tall socks, and a subtle pop of color or metallic for interest.

Oak + Fort

Oversized Trench Coat

7 colors available

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Old Navy

Full-Zip Hoodie Sweatshirt

8 colors available
sizes S – 4X

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Calia

Inspire High Rise 7/8 Legging

3 colors available
sizes XXS – 3X

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Saucony

Ride Millennium Sneakers

4 colors available

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5. With a turtleneck and fur coat

Let your fur coat do all the talking and keep the base simple with a monochrome turtleneck and leggings. A shorter, textured silhouette feels especially effortless here, while details like toggle closures add subtle interest without overwhelming the look. Finished with stirrup leggings and square-toe flats, the outfit feels intentional yet understated. And if you don’t own a fur coat, a colorful or textured statement coat delivers a similar impact with the same ease.

Lovers & Friends

Rhoda Faux Fur Jacket

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Quince

Cashmere Fisherman Turtleneck Sweater

8 colors available

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Quince

Andy Polarized Acetate Sunglasses

5 colors available

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Cole Haan

Nicolette Ballet Flats

3 colors available

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6. With a blazer and knee-high boots

There’s nothing easier—or chicer—than pairing leggings with knee-high boots. To balance the proportions, add volume and structure up top: while an oversized blazer and tee work on their own, layering a sweater in between adds depth and intention. Finish with an overcoat for warmth, and you’ve got a leggings look that works for just about any occasion.

Quince

Italian Wool Long Blazer

4 colors available

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AQUA

Cashmere V-Neck Sweater

4 colors available

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Steve Madden

Dantelle Boots

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DeMellier

The Miami Bag

8 colors available

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Shop Our Favorite Leggings

Spanx

Full-Length Leggings

7 colors available
sizes XS – 3X

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Eloquii

Miracle Flawless Legging

sizes 14 – 32

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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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Old Navy

High-Waisted Jersey Leggings

9 colors available
sizes XS – 4X

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GAP

Full-Length Leggings

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LANDS’ END

High Rise Ponte Polished Leggings

2 colors available
sizes 2 – 26 W

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437

Cloud High-Rise Leggings

10+ colors available

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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.

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