Everyone has different priorities when it comes time to get dressed—for some, it's all about ease. For others, looking good tops the list, whatever the cost. There are occasions where it's understandable to sacrifice practicality for style, but personally, I know that if I’m uncomfortable, it really doesn’t matter how head-turning my outfit is. My focus will rest on the hemline that keeps creeping up, or my pinky toe being steadily squished by the too-tight pair of heels. Even if I look outwardly on-point, the minor annoyance that lost to my vanity will be what I remember most.
If you similarly put comfort first, you probably own at least one pair of leggings. The WFH surge of 2020 saw most people give in to their unparalleled softness and ease. I know I was reaching for my H&M pair on an almost-daily basis.
But now that fashion has gone back to normal—or settled into a ‘new normal’, at least—the question arises: how can we hold onto our beloved leggings? This vital item deserves a spot in your everyday clothes roster, so I've turned my attention to outfit options for the here and now. With colder weather around the corner, we also have to factor cover-ups into the mix; thankfully, leggings lend themselves well to layered looks. Scroll on to see some of the best autumn-appropriate outfits styled around simple black leggings.
1. Button-Down Shirt + Pumps
Style Notes: A button-down shirt is timeless, and 2022 has seen it become the go-to cover-up over vest tops and racerbacks. Add leggings and ballet pumps and you've got yourself a super comfy, effortless outfit.
Shop the look:
Blue and white stripe works every time.
Soft and flattering; an irresistable combination.
A slightly smarter legging option.
Join the ballet flat renaissance.
2. Trench Coat + Trainers
Style Notes: Trench coats are ideal for autumn layering. Whether you're walking the dog or meeting your friends for lunch, a longline design and chunky kicks will make you feel suitably casual but stylishly put-together.
Shop the look:
Perfect for British weather.
This mid-rise cut is ideal for tucking T-shirts into.
There's something so fresh about white and beige paired together.
Always on the go? Meet your new best friend.
3. Oversized Jumper + Loafers
Style Notes: Striped knitwear is everywhere, so why not lean into the cosy styling and pair yours with some stirrup leggings? A pair of thick-soled loafers will smarten up the ensemble.
A sell-out style from & Other Stories—so don't sleep on it.
Stirrup leggings are so on-trend.
The loafer of the moment.
A flash of gold will instantly lift your look.
4. Layered Skirt + Heels
Style Notes: There's quite a lot going on in this outfit, but that's what makes it interesting. Play around with proportions and layer a skirt or dress over your leggings to make them night-out appropriate.
Corset-style tops aren't going anywhere.
I love the idea of this skirt with a navy turtleneck.
For regular leggings-wearers.
I'm all for a monochrome outfit, but sometimes a pop of green is just what you need.
5. Shearling Jacket + Uggs
Style Notes: On those chilly autumn days, choose ultra-snug items. If you're on the fence about UGGs, this outfit would also work with a pair of Birkenstock clogs.
Just enough shearling to keep you warm.
The satin waistband makes this pair extra-comfortable.
Like resting your feet on a cloud.
A staple addition to your accessories repertoire.
6. Knee-High Boots + Boxy Blazer
Style Notes: It's a known fact that blazers elevate every item—and leggings are no exception. Tuck them into sleek knee-high boots and finish off the outfit with gold-toned accessories.
Aligne's sustainably-made outerwear has reached cult status.
This hard-wearing pair will last for the long-haul.
I've been seeing lots of heeled knee-high boots, but this flat version feels more practical.
Charles & Keith always masters the LBB (little black bag).
Next up, the biggest autumn/winter 2022 fashion trends to know.
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No Trainers Needed—This Flat Shoe Trend Makes Leggings Look So Much PrettierBranch out.
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It’s Leggings-and-Flats Season—These Are the Combinations That Look the Chicest Right NowI've done the research.
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Claudia Winkleman's Leggings on The Traitors Are the Exact Pair Our Editors Have Been Buying for YearsEveryone should know about these.
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Move Over, Skinny Jeans, This "Dated" Trouser Trend Just Made an Unexpected Return for 2025It's got the A-list talking.
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Gwyneth Paltrow Just Wore the Leggings and Anti-Flat Shoe Combo I Never Expected to See Her InThis wasn't on my 2024 bingo card.
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Kendall Jenner Just Made Her Legging and UGGs Outfit Look Much Chicer Thanks to the Knit I Always See on ParisiansBalletcore for 2024.
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Hold the Jeans—Celebrities Have Confirmed They're Be Wearing Leggings and Boots All Winter LongI'll be doing the same.
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European Women Rely on This Elegant Coat Trend to Look Polished in Winter—18 of the Best for Every BudgetA modern classic.
