The Shoes We Never Wear With Cropped Leggings


(Image credit: AKM-GSI )

As you know, cropped leggings serve a variety of purposes. For starters, they're the perfect length if you're on the petite side, and of course they keep everyone cool during particularly sweaty workouts. It's why, just like you (and our favorite legging-loving celebrities), we're reaching for cropped leggings more often than not these days. But with cropped leggings comes a whole new set of challenges. Given that they can cut at an awkward place for many, they aren't the most versatile when it comes to shoes that complement them—at least in the eyes of our editors.

While we certainly stand by the "to each her own" philosophy, in case you're faced with a cropped legging–and–shoe pairing conundrum, we're here to share with you the shoe styles we avoid wearing with leggings (and what styles we turn to instead). So without further ado... Below, find out which shoes we never wear with cropped leggings, and shop cool cropped leggings at the end.


"Since I only wear cropped leggings to and from the gym, I stick with sneakers or comfortable slides. I don't see myself wearing any sort of boots with cropped leggings (unless it's a pair of Uggs and I'm back home in Kansas and it's snowing out—don't judge)." — Michelle Scanga 

Michelle's Pick


"I would never wear ankle boots with cropped leggings. Considering where the leggings end and the boots start, your leg will be visually chopped up in too many places. I prefer to wear sleek slides with my cropped leggings. I am loving this modern shearling pair from Parme Marin. These shoes make my cropped leggings feel just a tad more polished, whether I'm heading to and from Pilates or out running errands." — Lauren Eggertsen 

Lauren's Pick


"I definitely could never do stilettos of any height with cropped leggings. If I'm wearing them to a class that requires bare feet or a shoe change (e.g., barre or Spin), I'll choose a pair of classic sneakers to put on before and after class so that I look at least a little pulled together." — Allyson Payer

Allyson's Pick


"I'm personally not a fan of pool slides, which feel too chunky for me. Instead, I'd rather put on a pair of embellished slides, which are more flirty and suit my style better but are just as easy to slip on and off." — Erin Fitzpatrick

Erin's Pick


"I would never wear any type of ankle boots with cropped leggings. Besides the fact that the hem of the leggings and the top of the booties will likely meet at an awkward point on the leg, I'd much rather stick to the practical and sportier vibes that leggings suggest. These light, perforated slip-on sneakers would be a perfect match." — Gina Marinelli

Gina's Pick


"I reserve cropped leggings for the gym, so I would never pair them with sandals. The only shoes I'll wear with them are for working out. Right now, my favorite style is Nike's lightweight Roshe sneakers." — Kristen Nichols

Kristen's Pick


"I'd never wear high heels; that's so awkward. Instead, I always wear sneakers or Birkenstocks—comfortable, sporty, and cool." — Aemilia Madden 

Aemilia's Pick


This post was originally published at an earlier date and has since been updated.

Allyson Payer
Senior Editor

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.