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
Listen to Monica and buy the Reebok Classics.
For under $100 and years of style, you can't go wrong with these.
She's a skater girl.
The trendy "dad" shoe fashion girls can't stop wearing.
Admit it—your current Converse look like dirt.
Straight fire.
The wisest $40 you ever will spend.
Sporty and stylish all at once.
Sneaker-heads only.
The perfect cool but casual sneakers, if you ask me.
We stan. Get it?
Sneakers with just the right amount of chunk.
These sneakers look like they came back from the future.
What is it about designer sneakers that always makes them so tempting?
These are my personal favorite weekend sneakers.
I hear they are worth the splurge.
Wear these with sweats and a baby tank for a Hailey Bieber inspired look.
Quite the classic.
Because what's one more pair of white sneakers?
These days, the more retro the sneaker, the better.
These will go with everything, I promise.
Affordable and cute.
If you've never owned a pair of these, the time is now.
Lastly, a pair of Prada sneakers that I wish I owned.
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.
-
My Stylish 56-Year-Old Mom Is a Picky Shopper—31 Chic Under-$100Replica Store Finds She Approves OfCollarless blazers, Fair Isle knits, and Levi jeans inside.
-
If You're Going to Wear Leggings to the Airport in 2026, Pair Them With This Expensive-Looking ShoeIt's giving aspirational.
-
Introducing the Prettiest Legging Color Trend of 2026, as Worn by Maya HawkeBetter than black.
-
If You're Going to Wear a Sweater and Sneakers With Leggings This Winter, Choose Them in This Pretty Color TrendJ.Lo knows a good legging hue when she sees one.
-
Forget *It* Styles: These Back-to-Basics Sneakers Make Black Leggings Look Cool and ClassicThese shoes have been around for over 15 years.
-
Hold the Hoodies and Puffers—L.A. It Girls Are Wearing *This* Anti-Trend Item With LeggingsIf anyone knows a good legging outfit, it's Kaia Gerber.
-
If Chic Jeans-and-Boots Outfits Are the Goal, Don't Miss These Standout Picks From Zara, Madewell, andReplica StoreBring on a stylish fall-and-winter closet.
-
My Honest Take on the Winter It Boots Every Fashion Person Is Talking AboutFrom Khaite to Free People.
