Skinny jeans will never go "out," and that's a fact. Just take a look at any one of the handful of celebrities who seem to cling to the perennial denim staple. Season after season, we turn to these style stars to inform us of the freshest ways to style our skinnies, and according to them, all signs point to one boot trend in particular—riding boots—as the best boots to pair flawlessly with classic skinny jeans.
Kate Middleton has long been a fan of these flat, knee-high boots, and there are plenty of her outfits to get inspired by. They also happen to be approved by Mary-Kate Olsen. (When MK and Ashley wear something cool, you know we're quick to follow suit.) We spotted riding boots all over recent runways from a whole host of brands, such as Brandon Maxwell, Celine, and Bally, so if you're looking to get in on the trend, there's certainly no lack of options. Keep scrolling to see how Middleton and Olsen wear the equestrian trend, to see how they're styled on Instagram, and to shop the best riding boots for yourself.
On Celebrities
On Middleton: Penelope Chilvers Long Tassel Boots ($695)
This is a casual outfit formula Middleton tends to repeat often, involving a utility jacket, skinny jeans, and, of course, riding boots.
You'll wear these for years to come.
The sleekest riding boots for the city.
We've noticed how she sticks to dark neutrals with this combo. Black jeans and brown leather boots look so polished together.
It simply doesn't get any chicer than this Totême pair.
These have plenty of glowing reviews on Nordstrom.
Photographed at a horse show, Olsen wore traditional boots made for competition, but the equestrian trend can be worn well beyond the saddle.
The hardware on these feels especially fresh.
A pair of riding boots that are timeless and of-the-moment.
Angelina Jolie wore Tod's Timeless Boots ($1295) to run some errands in Los Angeles.
These boot come in wide-calf sizing ensuring that they'll fit like a glove.
Classic riding boots with a little edge.
On the Runway
Brandon Maxwell's F/W 20 runway show proved they're the perfect match for your skinny jeans.
The chain detail elevate this simple pair.
These are especially traditional.
Another recent example of the equestrian trend on the runway could be found in Celine's F/W 22 collection—a barn jacket was styled with skinny jeans and two-tone riding boots.
The perfect amount of height.
An A+ pair from Free People.
Riding boot styles were spotted in full force at Gucci's F/W 24 runway show, styled with (drumroll, please) hot pants. It's not skinny jeans, but another example of how the equestrian trend continues evolving.
The most coveted boot of the season.
Sublime. No notes.
If you wanted recent proof that the skinny jeans and riding boots pairing is back, look no further than Bally's F/W 24 runway show. The over-the-knee version of the riding boot silhouette shown in the show proves that we're strapped-into this trend.
Why not opt for an over-the-knee version while you're at it?
These affordable boots also come in tan and white, BTW.
On Instagram
A minimalist's dream pair.
These have so many positive reviews.
Riding boots have always been a great way to elevate basic black skinny jeans (see above).
Go posh with your styling by pairing your riding boots and skinny jeans with a blazer and turtleneck. It's a look that Kate Middleton would surely wear.
Simple perfection.
These Nordstrom favorites have a fair number of good reviews.
Grab a boxy blazer to re-create this casual and chic ensemble.
An investment pair you won't regret.
No one does equestrian boots like Frye.
Riding boots are a favorite among women in Paris, too.
Mango never misses the mark.
Another waterproof pair for the win.
This story was published at an earlier date and has since been updated.
-
I Thought I Hated Skinny Jeans, But These 5 Shoe Styles Make Them Feel Cool AgainMy redemption plan? Shoes.
-
If the Latest Shoe Trends Speak to You, You Better Listen—3 Standout PicksThese are already starting to sell out.
-
Sorry, But the UK Is Ahead of the U.S. With Trends—Here's What's Coming Up NextThe looks I see every time I leave the house.
-
These Are the Flat Boot Styles Trending in EuropeSo good, I want them all.
-
So *This* Is How to Make Bootcut Jeans Look Fresh in 2025It's clearly Canadian.
-
3 Chic Winter Pieces That Are Perfect for Mastering the Viral "Olsen Tuck" TrendPhoebe Philo is also known for doing this.
-
I've Lived in NYC and Boston—Here's Everything I Think Is Chic for WinterStay warm without sacrificing style.
-
New Yorkers Know That Wearing This Flat-Shoe Trend With Midi Skirts Makes Them Look CoolerYou can be the judge.
