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No matter what’s happening in their personal lives, Meghan Markle and Kate Middleton can agree on one thing: skinny jeans look great with riding boots. A few weeks ago, the Duchess of Sussex took to Instagram, sharing a sweet video of her family having fun at a pumpkin patch. Eagle-eyed fashion fans quickly clocked her CO Leather Riding Boots, which she styled over a slim pair of pants. The outfit formula is one that Middleton has relied on for over two decades, often breaking out her own brown Penelope Chilvers boots and rocking them with tried-and-true denim.
There’s no denying that the combo is a classic — one that transcends time and flatters everybody. So, if you’re wondering how to wear skinny jeans in 2026, take a tip from the royals and invest in some knee-length riding boots. Not only will they complement staples like skinnies and leggings, they’ll add interest to dresses and skirts, and (if you’re feeling daring) create a cool look when worn with shorts and tights. You also don’t have to break the bank when shopping for a new pair — we’ve found 13 must-have styles at different price points, allowing everyone to get in on this trend.
13 Pairs of Riding Boots To Style With Skinny Jeans
1. Standout Style: Sometimes the shoes make the outfit, and that’s especially true when it comes to Dream Pairs’ block-heeled boots. Between the eye-catching buckle and quilted back, they’ll really pop against your jeans-and-tee look.
2. Kate’s Favorite: The Princess of Wales was first spotted wearing her Penelope Chilvers tassel boots in 2004, and since then, has paired them with a variety of slim-fitting pants. While a splurge for many, the design has stood the test of time and is clearly worth the investment!
3. Sleek and Chic: Those who prefer something simple will have no problem styling Sam Edelman’s Equestrian Boots. While on-trend, they’re basic in the best way and will complement a variety of denim washes while still working with dresses and skirts.
4. Pop of Color: If you’re looking to spice up your cold-weather wardrobe, trade your typical brown and black styles for a deep burgundy shade. It’s a way to work color into your wardrobe while remaining neutral.
5. Luxe for Less: There are tons of deals to be had right now, especially at Walmart. For just $21, you can score a stylish pair of Time and Tru riding boots that reviewers swear are super comfy and “look a lot more expensive than they are.”
6. Meghan-Approved: The former Suits actress may have completed her fall outfit with a $1,195 pair of CO boots, but this pick from the same brand is super similar — and over $800 less.
7. Super Comfy: Need something you can sport all day? Dr. Scholl’s has you covered. The brand makes its own version of riding boots with extra cushioning in the soles, so you won’t have to worry about your feet aching after hours of standing or walking.
8. Wide Calf: Nothing is more annoying than ordering a pair of boots only to find they won’t zip over your leg. Save yourself the trouble with Kelly & Katie’s Shry Boot, available in both standard and wide sizes.
9. Worth the Splurge: There’s a reason Stuart Weitzman shoes constantly pop up on the red carpet. The label knows how to make quality footwear that’ll last for years to come, and while its over-the-knee boots have been a mainstay in celebrity wardrobes, the Soluxe Celia Knee High Boot is a worthy competitor — just look at that dainty chain detail!
10. Stylish Suede: Elevate your sweaters and seasonal staples by choosing faux suede rather than leather. While under $100, this pair “exceeded” shoppers’ expectations. Many note they are cozy, comfortable and “look even nicer than the pictures.”
11. Make It Moto: If slim-fitting riding boots aren’t quite your style, you can always go with their equally trendy relative, the moto boot. A bit more rugged and boxier, it’ll slip on over your skinnies without issue, and amp up your outfit in a cool, model-off-duty way.
12. Lug Sole: Add interest to your outfit with a lug sole option. Not only does the thicker heel play around with proportions and balance out skinny pants, but this one has a stretchy back, so you won’t have to worry about it feeling too tight.
13. Currently Trending: Something we love about riding boots is that they never go out of style. However, if you’d like to give your shoe collection a modern update, say yes to banana boots. The bold color choice has seen a surge in popularity, and reviewers compare this pick to one from Frye that’s a lot pricier.
