What to Wear With Leggings In The Winter: 12 Easy Outfit Ideas
Photo Credit:@camillemontagnac
Let me start with a confession: leggings are the one item I refuse to overthink. They’re comfortable, they’re practical, they work for school drop-off, busy mornings, errands, work-from-home days — everything.
The real question isn’t if you should wear leggings. It’s what to wear with leggings so the outfit feels intentional instead of “I ran out the door in a panic.”
After hearing so many readers ask about which long sweater to wear with leggings and what are some cute outfits to wear with leggings, I decided to break down the formulas that actually work in real life not the runway versions that require five layers and a prayer.
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Read This:
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1. Long Sweater + Black Leggings + Tall Boots
This is the blueprint for winter. The long sweater adds coverage, the boots add structure, and suddenly your leggings look like an outfit — not pajamas.
MANGO
Taldote Turtleneck Long Sleeve Sweater Dress
$48.99
Lands' End
High Rise Serious Sweats Fleece Lined Pocket Leggings
$41.97
Söfft
Taryn Knee High Boot
$259.95
2. Oversized Button-Down + Leggings + Ballet Flats
The balance is what makes this look good: structured on top, soft on the bottom. Perfect for casual office days or lunch runs.
Amazon
Oversized T Shirts Button Down
$32.99
Amazon
CRZ YOGA Butterlift Workout Leggings
$32.00
Amazon
Knit Ballet Comfortable Dressy Slip On Flat
$32.99
3. Puffer Vest + Leggings + Base Layer
Think “morning walk, but make it chic.” Add sneakers and a crossbody and you’re done.
LAMARQUE
Melicia | Reversible Puffer Vest
$295.00
Amazon
Long Sleeve Shirts
$19.99
Amazon
High-Waisted and Wide Leg
$29.99
4. Blazer + Leggings + Sleek Turtleneck
A power move. This is your “I have meetings but still want to be comfortable” look. Works with ankle boots or loafers.
Kenneth Cole
Oversize Luxe Twill Jacket
$159.00
BP.
Turtleneck Rib Top
$29.50
Amazon
No Front Seam Straight Leggings
$35.99
5. Denim Shirt + Leggings + Shearling-Lined Clogs
A little rustic, a little cozy, and extremely cute. This is an unexpected cute outfit to wear with leggings that always looks stylish.
Amazon
Lioness Women's Off Duty Denim Shirt
$79.00
Commando
Control Top Faux Leather Leggings
$128
Tory Burch
Mellow Faux Shearling Lined Mule
$325
6. Long Cardigan + Leggings + Simple Tee
Soft, easy, and foolproof. Go monochrome to look instantly put together.
Amazon
Oversized Long Cardigan
$52.99
Amazon
Stretch Skinny Capri Pants
$16.97
Madewell
Perfect Crewneck T-Shirt
$45.00
7. Athleisure Set + Wool Coat
This trend isn’t slowing down. Throwing a tailored coat over activewear makes the whole outfit feel elevated.
Amazon
2 Piece Seamless Ribbed Workout Sets
$45.95
Amazon
Cardigan Sweater Open Front
$49.99
8. Hoodie + Leggings + Statement Jacket
A moto jacket, bomber, or sherpa jacket works best here. It’s casual but edited.
Favorite Daughter
The Collegiate Graphic Hoodie
$118.00
Maris Ponte Leggings
LE BOP Maris Ponte Leggings
$138.00
Amazon
Leopard Long Wool Trench Coat
$65.99
9. Chunky Knit + Leggings + Chelsea Boots
This is the winter classic. It’s warm, comfortable, and looks good on every body shape.
Amazon
Turtleneck Oversized Sweater
$46.99
Commando
Faux Leather Flare Leggings
$148
Nordstrom
Darian Water Resistant Chelsea Boot
$129.95
10. Tunic Top + Leggings + Knee-High Boots
If you love coverage but still want definition, this is the sweet spot. Add a belt if you want more structure.
Free People
Chelsea V-Neck Tunic Sweater
$198
Lysse
Lyssentials High Waist Denim Leggings
$98
Circus NY by Sam Edelman
Billie Knee High Boot
$189.95
11. Quilted Jacket + Leggings + Platform Sneakers
A little sport, a little street. Perfect for transitional weather.
Caslon®
Quilted Leather Jacket
$299
Amazon
High Waisted Stretchy Jeans Jeggings
$39.95
adidas
Gazelle Bold Platform Sneaker
$120
12. Long Sleeve Bodysuit + Leggings + Oversized Scarf
This is your “errands but cute” look. The bodysuit smooths the base, the scarf adds interest, and the leggings keep everything easy.
Princess Polly
Mayok Rib Bodysuit
$50.00
Hue
Crosshatch Slit Hem Denim Leggings
$68.00
Amazon
Pashmina Shawl Wrap Scarf
$22.99
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