5 Things You Should Never Wear With Leggings

For a bit of stretchy fabric you wear to the gym, leggings have become something of a hot potato in recent times. There was the brouhaha caused when United Airlines banned two teenage girls in Denver from boarding a flight for wearing leggings. More column inches than you might have expected were dedicated to whether this decision was sexist—a United spokesman said “absolutely not”—and whether it is, in fact, appropriate to sport leggings out and about when you certainly have no intention of breaking into burpees or jumping jacks.

If you’re familiar with the off-duty wardrobes of supermodels (Kendall Jenner, Gigi Hadid, Miranda Kerr, Gisele Bündchen, and so on), then you’ll know that leggings are the backbone. Jenner wears hers with hi-vis yellow jackets and Louis Vuitton bags while Kerr favours the leathery kind that fits like sausage casings. Man Repeller founder Leandra Medine wears her white Outdoor Voices pair with mules from The Row and a quilted satin jacket that wouldn’t look out of place on HRH, as well as with New Balance trainers and a sparkling Chanel bag.


The Style Stalker; PICTURED: Caroline Daur wearing stirrup leggings (and getting it right) at London Fashion Week

Medine’s styling proves that if you treat them like jeans, pretty much anything is fair game. You can’t go (far) wrong with plain black leggings—Nike Epic Lux Running Tights (£80) are a winner, as are the Varley Hillcrests with mesh inserts (£90). Another point worth mentioning is that stirrup leggings really are a gift to legs. They look more like trousers than leggings—confusing but true—and seem to work with everything from roomy double-breasted blazers to ruffled floral dresses and polo neck jumpers (Balenciaga’s stirrups will set you back £545 while H&M has a brilliant patterned pair in grass-green for £35). If the word “stirrup” has made you even more nervous, here are five commandments to memorise before approaching leggings this season.

NO: Leggings With Denim Shorts

It takes a real pro to tuck leather leggings under skintight denim shorts and still be able to walk, but the models at Alexander Wang’s spring 2018 show in New York managed it with aplomb. Still, for us mortals, it’s worth bearing in mind that one bottom half is probably enough if you don’t want to get gawped at going about your business.

YES: Leggings With Long Layers


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If you still want some coverage, step away from the Daisy Dukes and invest in a long-line sweater to neatly skim over your leggings.

NO: Leggings With Shearling Boots

Sienna Miller just about got away with wearing cropped leggings with Ugg boots and a bowler hat, but then she does have the fact that she’s Sienna Miller on her side. Sadly, the rest of us will look like we’ve stepped out of a Tardis and emerged in the early noughties—never a good thing.

YES: Black Leggings With Black Ankle Boots


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The most slimming option on the planet. Fact.

NO: Leggings Worn Under Dresses

You can blame the weather for this one. Raise your hand if you’ve wanted to get one last wear out of your favourite summer dress, but there’s been a nip of cold in the air. Now keep it up if you reached for leggings. Totally understandable decision, but leggings under dresses tend to look like you’ve got changed in the dark unless you’re of Amazonian height. Next time, try opaques.

YES: Leggings Under Coats


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A little peekaboo legging (especially when worn with kitten heels) feels delightfully '80s, which in turn is so right for now.

NO: Leggings With Slippers

Leandra Medine Instagrammed herself wearing knee-length leggings, a bandana scarf and Natasha Zinko’s fluffball slippers. The photo’s caption: “I consider this outfit my greatest accomplishment of 2017.” More than 11,000 likes later, it’s tempting to dust off your home slippers and take them for a spin outside, but we bet you only get as far as the recycling bins.

YES: Leggings With Heels


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No chance of going to the gym in these…

NO: Old, Worn-Out Leggings

This sounds like a no-brainer, and yet it's hard to get rid of those comfy black jersey leggings when they’ve been so faithful, so supportive and so easy to wear over the years. Truth is the more tired-out the fabric, the less likely it’ll be to do good things for your legs and bum—plus, who doesn’t enjoy buying a new pair?

YES: Leather Leggings (for a Change)


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If you’re feeling really adventurous when it comes to purchasing new leggings, we’d recommend going for red and for leather—very A/W 18.

Next up: your ultimate guide to this season’s ankle boots.