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

"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

"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

"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

"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

"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