Fashion’s love affair with leggings plays out like a dramatic Netflix rom-com; there have been highs, which, of course, bring with them the lows, but in the end, you know they’re meant to be together. After reaching something of a sartorial peak in the ’80s and early ‘90s, leggings fell out of favour, replaced by other stylish trouser options, such as low-rise jeans, parachute pants, and pedal pushers. What a time it was to get dressed! Then, we witnessed a legging resurgence in the early ’00s by way of leather-look styles and jeggings. Now, however, we’ve settled into a significantly chicer leggings moment, where black and tonal leggings reign, and people are styling them for all occasions in a variety of sleek ways.
While I could fill an entire gallery with impressive leggings outfits for you to peruse, I know your time is precious. So I’ve whittled down seven outfits that perfectly illustrate how to wear leggings now and in the most stylish ways possible. From casual get-ups you can throw on at whim to elevated looks that can carry you into evening territory, these ensembles cover all your leggings bases. Scroll on to see them.
Style Notes: Keep things simple with a monochrome palette involving a knit, tailored coat, and knee boots.
A classic coat you’ll wear for life.
As versatile a jumper as I’ve ever seen.
I swear by these leggings.
The thin heel makes these knee boots feel so current.
Style Notes: Leggings look their sleekest with classic wardrobe items—cue a camel blazer, Breton stripes, and never-date Converse.
Seriously affordable.
Our editors continue to be infatuated with the Breton knit.
The front splits will showcase a standout shoe moment.
Converse kicks never date.
Style Notes: For a look that can take you from work to a dinner date with ease, you can rely on an crisp white shirt, staple black leggings, and glossy knee boots.
In my opinion, this is the perfect length for wearing with leggings.
Ribbed leggings make for a chic change to basic jersey.
Mock croc textures never go out of style.
Style Notes: Split-hem leggings are ideal for showcasing a standout shoe moment, so what better way to wear your box-fresh kicks? Throw in a leather biker and you’ve got the perfect downtime outfit mix.
I love this vegan leather biker.
These leggings come in an extended size range.
If you want your outfits to look current, just add a pair of New Balance.
Style Notes: We all rely on the failsafe combination of jeans and a nice top, but leggings and nice tops are just as amenable.
This colour is so beautiful.
This will work with so many outfits.
These leggings are thicker than your average, making them ideal if you want to stay toasty.
Fashion’s favourite mule.
Style Notes: Leggings are the perfect canvas to interesting layering combinations. Take Sarah’s blazer/hoodie combination, which strikes the perfect balance between casual and polished. The boots and leggings also echo this sentiment.
A true classic.
If you’re looking for a premium hoodie, it’s gotta be Pangaia.
A soft cotton pair at a very reasonable price.
The perfect black knee boot does exist.
Style Notes: A follow-on from the above look, leggings and sweatshirts go hand-in-hand as a solid low-key outfit option, which you can then elevate with a classic bag and pearly earrings.
Anine Bing creates some of the coolest sweatshirts around.
This bag will never not be on my wish list.
High-waist leggings create the sleekest silhouette.
This story was originally published at an earlier time and has since been updated.
