The Word Is Out: Never Wear These Shoes With Leggings

There is no denying that leggings have become a streetwear staple in the wardrobes of nearly every It girl in existence. Remember the great debate of whether or not leggings were pants? Well, that's been put to rest, as celebrities like Gigi Hadid and Chrissy Teigen not only wear them on the regular, but they style them in ways unthinkable. In case you weren't aware, Gigi and Chrissy have the same stylist, Monica Rose, and during a three-day trip hosted by Reebok, I had the opportunity to interview the genius herself.
Curious to pick her brain on all things legging- and sneaker-related, I first asked Monica what the best sneakers to wear with leggings are. She said, "I think a [Reebok] classic leather is good to wear. I just think it's such a comfortable shoe. When I wear them, I'm excited for work and excited to be comfortable. But for leggings, I think any sneaker really goes with them." If you aren't familiar with the Classic Leather sneakers Monica speaks so highly of, don't worry, we shopped out the best colors below.
In addition to the best sneakers to wear with leggings, I asked Monica what the one item was she would never style with leggings. Without hesitation, she clearly stated to consider leaving your thigh-high boots at home. If Monica Rose, the mastermind behind some of the most memorable looks in fashion right now, says she would never put thigh-high boots with leggings, that means the powerful clan that is Monica's clients won't be wearing that boot style with leggings anytime soon.
Go on to shop the sneakers Monica Rose says look the best with leggings, including the Reebok Classic Leather style.
Shop Sneakers That Look Good With Leggings
Up next, find out how to find the perfect swimsuit, period.
This press trip was paid for by Reebok. Editor's opinions are her own.
This post was originally published at an earlier date and has since been updated.

Lauren Eggertsen is currently the editorial director of Who What Wear and has worked at the company for over nine years, where she started as an associate editor and has since worked her way up. Lauren has worked in the Los Angeles and New York Who What Wear offices but currently calls L.A. home. Here, she leads and manages Who What Wear's editorial team and oversees all editorial content. Lauren's role also includes helping to set the fashion direction for all original photo shoots and often styles many celebrity cover shoots, including big names like Kaia Gerber, Normani, and Sabrina Carpenter. She has also attended multiple fashion weeks, including New York, London, Milan, and Paris, where her style has been featured on sites such as Vogue, Harpers Bazaar, and Elle.
-
Whenever I'm in Paris, I See This Boot Trend Styled With Minidresses in Every Vintage Shop and Local Bistro
Sorry, ankle boots, but it's not you.
-
Everyone in Los Angeles Knows This Shoe Trend Makes Denim Shorts Look Way Cooler
Denim shorts never looked so good.
-
Spotted at Wimbledon: The Anti-Summer Shoe Trend You Don't Usually See in the Stands
Never too hot for these.
-
Believe Me—You'll Still Want These 36 Items in 2026 (and '27 and '28)
Timeless with a capital T.
-
The $140 Boots London Fashion Girls Take Out of Storage Every Summer to Wear With Shorts and Dresses
From Kate Moss to Daisy Edgar-Jones.
-
Put a Hold on Your Black Leggings—This Fresh Color Trend Is the One You'll See Everywhere This Summer
The "just right" shade that feels fresh and elegant for 2025.
-
Hold the Sneakers: *This* Is the Stylish Shoe Trend Fashion People Are Wearing With Leggings to Pilates
Kendall Jenner is leading the way.
-
Stop With the Ankle Boots—Miniskirts Should Only Be Worn Like *This* in 2025
Period.