5 Things Our Editors Never Wear With Leggings, Plus 5 They Always Do

Given their form-fitting silhouette, it's safe to say leggings come with a set of rules that exceeds those of other articles of clothing. But given how comfortable and cool leggings have the potential of being, we'd say that putting a little extra thought into your legging look is worth the effort.

The legging trend has been back with a vengeance for a couple of years now and we've grown accustomed to seeing celebrities and catwalk show-goers wearing them instead of trousers—and in some instances, as a carefully considered extra item. (Who'd have thought that leggings with a skirt or sexy, suede boots could be so desirable?)

To achieve the most forward look, there are certain pieces that we'd personally recommend skipping when donning the athleisure staple. Of course, style is personal, so there's no right or wrong answer when it comes to styling leggings. But if you're interested in how our editor's are currently styling theirs, then keep on scrolling. 

Read on to find out which five styling options our editors are less intrigued by right now, and what they're reaching for instead. 

Wouldn't Wear: Shacket

Wear: Oversized Blazer


(Image credit: @simplytandya)

"If I'm going to wear leggings out and about (and not for exercise purposes), I'd prefer to find a way to dress them up rather than lean into casual. This is purely a personal preference, but I really like the slightly '80s idea of an oversized blazer with leggings. You can make this work with heels, flats or trainers."—Hannah Almassi, Editor in Chief. 

Wouldn't Wear: Ballet Flats

Wear: Loafers


(Image credit: @symphonyofsilk)

"As much as I'm enjoying the ballet flats trend, when it comes to styling leggings, I always opt for loafers. The combination of delicate ballerinas and leggings can feel a bit on the nose, so a pair of chunkier, more structured loafers add a much needed contrast."—Emily Dawes, Affiliates Editor

Wouldn't Wear: Crop ToP

Wear: Long Top


(Image credit: @taniceelizabeth)

"The combination of a crop top and leggings has never appealed to me, perhaps because it's so predictable. To take my leggings further, and add a more directional feel, I opt for longer layers on top to remove the sporty feel."—Joy Ejaria, Social Media Editor.

Wouldn't Wear: Denim Jacket

Wear: Moto Jacket


(Image credit: @nlmarilyn)

"The denim jacket and leggings formula feels predictable at this point, but the emerging trend of moto jackets, especially vintage look ones lend themselves so well to a leggings outfit formula that it would be wrong to deny the pairing."—Remy Farrell, Shopping Editor. 

Wouldn't Wear: Mary Janes

Wear: Point Toe Shoes


(Image credit: @rosiehw)

"When styling leggings for dressier occasions than running errands, pointed heels are my go-to. Though Mary Janes are definitely one of the trending shoes du jour, the leg lengthening effect of a sharp, pointed-toe heel should not be overlooked."—Maxine Eggenberger, Deputy Editor. 

Next Up, The Autumn/Winter 2023 Fashion Trends That Really Matter

Florrie Alexander
Acting Affiliates Editor

Florrie embarked on her fashion journey while studying French and History at university. Whilst studying in Aix-en-Provence, she began to write her dissertation on the history of fashion and the influence of Haute Couture, and landed her first role at Harper’s Bazaar. Following this, she interned for various publications including Elle, Grazia and Marie Claire before joining the fashion team at Conde Nast Traveller. There, she contributed to international photoshoots, styled pages and covers, and produced engaging digital content.

During a freelance period, Florrie honed her skills in editorial work in various digital and print publications including Vogue Italy and Departures magazine, as well as styling e-commerce photoshoots and personal shopping. Florrie actively pursues an in-depth understanding of fashion and jewellery, and after styling a jewellery cover shoot at Conde Nast Traveller chose to complete the De Beers Diamond Foundation course. Florrie first joined Who What Wear UK as a freelancer before becoming the Commerce Writer, blending both editorial and commercial content. Now, as the Acting Affiliates Editor, she monitors current trends, new-in styles, wardrobe heroes and how best to style them. In her downtime, Florrie can be found in her hometown of London, usually with a coffee in hand.