Let's Talk About Leggings—Here's What to Wear With Them in 2024
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 looks that make leggings actually look chic. From wearing them with a midi skirt to teaming them with knee-high boots and a blazer, here are nine outfits that have unintentionally persuaded me to wear leggings.
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.
SHOP THE LOOK:
These breathable and lightweight leggings from Free People are great for those who are always on the go.
A cap is a streetwear staple and this one from Jacquemus oozes subtle luxury.
I own a pair of Nike's P-6000's and they are the comfiest trainers I have tried.
2. Stirrup Leggings + Jumper + Trainers
Style Notes: My mum definitely wore them in the '80s with court heels, and now, stirrup leggings are back. Tanice shows how to make them feel fresh with cool kicks and a bold knit. I'm completely sold.
SHOP THE LOOK:
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.
SHOP THE LOOK:
From the gym to running errands, this Booty Boost style from Spanx is a great transitional pair of leggings - they even have a hidden pocket in the waistband.
Peaked lapels elevate any blazer, just like this one from & Other Stories.
These leather ankle boots have a slight equestrian feel to them, with their contrasting wooden block heel and comfortable insoles.
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.
SHOP THE LOOK:
If you're looking for a body-hugging option to lounge in, these thermal ribbed leggings from SKIMS might just be the answer.
Mango is known for its expensive-looking outerwear and this woven biscuit-coloured design encaspulates exactly that.
This lightly padded cross-body bag is perfect for quickly chucking bits and bobs in before heading out the door.
Accessories are a great way to add a pop of colour to your wardrobe.
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.
SHOP THE LOOK:
Following the recent clog trend, these Chloe Marcie sliders sport a designer-engraved buckle embellishment and a cosy shearling lining.
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.
SHOP THE LOOK:
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.
Loafer season is back in full swing and what better way to hop on the trend than with this Prada patent leather option?
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.
SHOP THE LOOK:
This stretchy style from Lululemon boasts the much-loved contoured effect of leggings.
Mirror Lina's look with this high-neck jumper from Mango.
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.
SHOP THE LOOK:
You'll get so much wear out of these faux leather leggings from Commando.
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.
SHOP THE LOOK:
Do I even need to say anything about this relaxed-fit poplin shirt?
This piece was published at an earlier date and has since been updated
Next Up: 6 Simple Winter Outfits That Are the Epitome of Timeless
Harriet Davey is a freelance fashion editor who has been part of Who What Wear's extended team since 2017. She previously worked in print at Look magazine and has since worked across print, digital and social for many other titles, including British Vogue, Stylist, Grazia, Refinery29 and Marie Claire. Also a stylist, Harriet has had the pleasure of producing cover shoots and editorials along with commercial shoots for brands including Boux Avenue, Watches of Switzerland, Benefit Cosmetics and Revolution. To add to this, Harriet also works in live TV styling for ITV’s This Morning.
Back to Who What Wear. With hundreds of published stories on site, Harriet knows what the WWW reader wants. Keeping up to date with the latest It buys and runway trends, she can guarantee to keep you one step ahead of the most stylish people.
When not writing or styling, Harriet loves to go shopping (yes, more fashion). If she’s not in a local Hackney bar or restaurant, you can find her forever searching for her next holiday destination.
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