If I'm honest, I've never really been into leggings. Although, you would think I'm lying if you saw how many activewear styles I have, sat there ready and waiting in case I ever set foot in the gym I pay monthly for. But when it comes to leggings to wear as part of a daily uniform, I've always avoided them—until now, that is. And it's thanks to all of the outfit inspo on Instagram.
While it's tricky to find a pair that doesn't bag at the knees and sag at the crotch, so many brands—including Commando, Spanx and Toteme—have nailed it with well-fitting styles. It's all about getting the right thickness, too. Unlike opaque tights, you don't want them to be sheer, as this is what can make them look cheap and scruffy. Instead, thicker (more luxe) materials with details such as stirrups, split hems and a second-skin fit are what to look for.
Sure, it's easy to wear leggings off-duty with an oversized sweatshirt and trainers, but as someone who is often overdressed, I'm all for the outfit ideas that make leggings actually look chic. From wearing them with roll neck to teaming them with knee-high boots and a blazer, here are nine outfits that have unintentionally persuaded me to wear leggings.
9 Winter Leggings Outfits That Will Look So Chic In 2025:
1. Leggings + Crewneck + Blazer
Style Notes: Kim styles the perfect off-duty look with a crew-neck jumper, chunky trainers and a covertly casual cap, whilst also layering a boxy blazer over top. This is one I want to recreate.
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A cap is a streetwear staple and this one from Jacquemus oozes subtle luxury.
Arket's Hopsack blazer is a firm favourite amongst our editors.
What's not to love about a grey marl sweatshirt?
These breathable and lightweight leggings from Free People are great for those who are always on the go.
I've heard Nike's P-6000's and some of the comfiest trainers around.
The puzzle bag is still going strong in fashion insider's wardrobes.
2. Leggings + Hoodie + Trainers
Style Notes: Okay, so this is the most obvious way to wear leggings, but if it isn't broke, hey? Adding a hoodie and trainers is an easy way to go about running errands, heading to a gym class or out for a long walk with the added layer of a maxi coat.
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Grab in a size up to make sure it's a good length over the leggings.
Uniqlo's Heattech will keep you so warm all winter.
To carry everything in.
Big fan of this colourway.
3. Leggings + Blazer + Knee-High Boots
Style Notes: I've seen so many people wearing knee-high boots over leggings or skinny jeans again. A glossy pair of rider boots with a wool blazer à la Anouk is always a good idea.
Peaked lapels elevate any blazer, just like this one from & Other Stories.
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From the gym to running errands, this style from Spanx is a great transitional pair of leggings––they're super high waisted for extra comfort.
I've been thinking about these for a long long time.
Throw in everything and go.
4. Leggings + Double-Breasted Coat + UGG's
Style Notes: Borislava shows us that the UGG hype is still in full swing with this dressed-down number. Paired with a knit beanie, handy cross-body bag and relaxed-fit coat, this look champions smart-casual.
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Accessories are a great way to add a pop of colour to your wardrobe.
COS is known for its expensive-looking outerwear and this biscuit-coloured design encaspulates exactly that.
If you're looking for a body-hugging option to lounge in, these thermal ribbed leggings from SKIMS might just be the answer.
It also comes with a cross-body strap.
No explanation needed.
5. Leggings + Quilted Jacket
Style Notes: Marilyn styles the sell-out Frankie Shop quilted jacket (you know the one) with a classic pair of leggings and clogs. While I'm not sure about clogs for myself, this outfit certainly makes me want to go wild and try them out.
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Quilted jackets are still a winter hero item.
Nail your capsule wardrobe with these timeless TOTEME leggings.
Chloé made us do it.
6. Grey Leggings + Leather Jacket + Midi Skirt
Style Notes: While most people swerve away from grey sweat-showing leggings when working out, they totally work for the day. The more layers the merrier for winter, and Linne makes a strong case for a midi skirt over her pair.
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The cult style is also now available in khaki.
You can't go wrong with a classic roll-neck.
Mango makes such effortless pieces and this wool midi skirt is one of them.
Not only are these leggings great for layering and lounging, but they're also made using a thermal fabric to keep you warm during the cooler weather.
Loafers will see you through all seasons.
7. Leggings + Knit Roll-Neck Jumper + Chunky Boots
Style Notes: This outfit screams winter in the city. Focused totally on practicality and layering, Lina opts for a knitted roll-neck jumper underneath a smart wool blazer, before completing the outfit with a camel coat.
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Yes to everything about this caramel wrap coat.
Padded shoulders, notched lapels, front flap pockets? I'm sold.
Mirror Lina's look with this high-neck jumper from H&M..
This stretchy style from Lululemon boasts the much-loved contoured effect of leggings.
I think there's something so chic about a chunky knee-high boot.
8. Leggings + Faux-Fur Coat + Chunky Boots
Style Notes: As a big fan of Janka's fun looks, I appreciate this from top to toe. While leggings are the simple base to this whole outfit, it's all about keeping the rest of the vibe big, bold and cosy.
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Faux fur coats are having a moment.
You'll get so much wear out of these faux leather leggings from Commando.
A staple.
9. Split Leggings + White Shirt + Heels
Style Notes: If in doubt, keep it simple. An oversized crisp white shirt is the perfect companion to a pair of leggings. And this split-front style is the attention-to-detail iteration that minimalists swear by.
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Do I even need to say anything about this relaxed-fit poplin shirt?
A split hem brings so much more to a pair of regular leggings.
I always have a pair of Manolo Blahnik's heels on my wishlist.
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