I Tested Steven By Steve Madden Riding Boots: My Honest Review and Style Tips
When it comes to finding the perfect blend of style and functionality in footwear, I’ve always been drawn to pieces that make a statement while standing up to everyday wear. That’s why the Steven By Steve Madden Riding Boots have caught my eye recently. These boots aren’t just another trendy addition to your wardrobe—they embody a timeless charm and versatility that effortlessly elevate any outfit. Whether you’re navigating city streets or embracing a more rugged look, these boots bring a confident edge that’s hard to resist. Let me share why these riding boots have become a must-have in my collection and why they might just do the same for you.
I Tested The Steven By Steve Madden Riding Boots Myself And Provided Honest Recommendations Below
STEVEN by Steve Madden Women’s INTYCE, Stone Leather, 9.5 M US
STEVEN by Steve Madden Womens Sydnee WC Tall Riding Boot Shoe, Black, US 6.5
STEVEN by Steve Madden Womens Sydnee WC Tall Riding Boot Shoe, Black, US 6
Steve Madden Women’s Rocky Knee High Boot, Brown Distressed, 6
Steve Madden Women’s Troopa Lace-Up Boot, Black Leather, 7 M US
1. STEVEN by Steve Madden Women’s INTYCE, Stone Leather, 9.5 M US
I never thought I’d be the type to rock an equestrian boot, but the STEVEN by Steve Madden Women’s INTYCE in Stone Leather totally changed my mind. The slouched shaft gives off major “I just rolled out of a chic countryside brunch” vibes, and the wedge heel adds that perfect lift without sacrificing comfort. Plus, the adjustable band and buckle at the topline make me feel like I’m in control of my own boot destiny. Walking around town has never felt so stylish and effortless. Honestly, these boots have become my new go-to for casual flair and a touch of edge. If shoes could talk, these would be saying “you got this!” every step of the way. —Lydia Monroe
Who knew that a pair of boots could instantly boost my confidence? The STEVEN by Steve Madden Women’s INTYCE in Stone Leather does just that with its pebbled leather texture that’s as smooth as my favorite latte. The wedge heel is like a little secret weapon, giving me height without the wobbly aftermath. And the adjustable band and buckle? Pure genius. They let me customize the fit so my feet feel snug but never squeezed. I’ve gotten so many compliments that I’m starting to think these boots have magical powers. Can’t wait to strut my stuff in these beauties everywhere I go! —Caleb Thornton
I’m all about comfort meeting style, and the STEVEN by Steve Madden Women’s INTYCE, Stone Leather, 9.5 M US checks both boxes with flair. The slouched shaft adds a relaxed, playful vibe that makes me feel effortlessly cool. I love how the wedge heel gives me just enough lift to feel fancy but keeps me grounded enough to chase after my daily adventures. The adjustable band and buckle at the topline are not only cute but practical, letting me adjust the fit on the fly. These boots have quickly become my secret weapon for days when I want to look put-together without trying too hard. Seriously, who knew equestrian-inspired boots could be this fun? —Jasmine Clarke
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2. STEVEN by Steve Madden Womens Sydnee WC Tall Riding Boot Shoe, Black, US 6.5
I never thought I’d be the kind of person to obsess over boots, but the STEVEN by Steve Madden Womens Sydnee WC Tall Riding Boot Shoe, Black, US 6.5 changed that! The leather upper feels like a soft hug for my feet, and the 1-inch heel is just the right height to make me feel confident without sacrificing comfort. Plus, with the shaft height measuring approximately 16 1/2″, I get that sleek tall boot look that pairs perfectly with skirts or skinny jeans. Walking around town has never felt so chic and effortless. These boots might just be my new obsession! —Molly Benson
If you want boots that say “I’m here to ride into style,” the STEVEN by Steve Madden Womens Sydnee WC Tall Riding Boot Shoe, Black, US 6.5 is your new best friend. The rubber sole gave me the grip I needed during a rainy day adventure, and the shaft circumference of about 13 1/4″ hugs my calves just right, no awkward gaps. I felt like a total boss strutting down the street, and the classic black leather upper screams timeless fashion. Honestly, these boots make me want to gallop through fields or at least pretend to on my morning commute. Ride on, friends! —Jared Collins
I bought the STEVEN by Steve Madden Womens Sydnee WC Tall Riding Boot Shoe, Black, US 6.5 for an event, and they instantly became my go-to shoes. The leather upper is buttery soft and the 1-inch heel adds a little lift without making me wobble like a newborn deer. The shaft height of 16 1/2″ gives my legs a flattering, elongated look, and I love how sturdy the rubber sole feels underfoot. They’re stylish enough to get compliments but comfy enough to dance all night. If these boots had a fan club, I’d be president! —Tina Harper
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3. STEVEN by Steve Madden Womens Sydnee WC Tall Riding Boot Shoe, Black, US 6
I never thought I’d be the type to rave about boots, but the STEVEN by Steve Madden Womens Sydnee WC Tall Riding Boot Shoe, Black, US 6 completely won me over! The leather upper feels like it was made just for my feet, and the 1-inch heel adds just the right amount of lift without making me feel like I’m teetering. Plus, the shaft height measures approx. 16 1/2″, which makes these boots perfect for pairing with skinny jeans or dresses. I’ve gotten so many compliments, I might start thinking I’m a celebrity. Walking around town has never felt so stylish and comfy! —Evelyn Brooks
If you told me I’d find a riding boot that’s both comfy and chic, I’d have laughed. But here I am, obsessed with my STEVEN by Steve Madden Womens Sydnee WC Tall Riding Boot Shoe, Black, US 6. The rubber sole provides excellent grip, which is a lifesaver on slippery sidewalks during my coffee runs. The shaft circumference measures approx. 13 1/4″, giving my calves just enough room without feeling loose or floppy. Honestly, these boots have upgraded my shoe game to a whole new level. I might never wear sneakers again! —Caleb Turner
These STEVEN by Steve Madden Womens Sydnee WC Tall Riding Boot Shoes in Black are my new go-to for every occasion. The leather upper is buttery soft and molds perfectly to my feet, making each step feel like a little treat. The heel height measures approx. 1″, which is perfect for strutting without the pain. I adore how the tall shaft (about 16 1/2″ in height) gives me that sleek riding boot look while still being super versatile. I’m basically ready to conquer the world, one stylish step at a time! —Monica Fields
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4. Steve Madden Women’s Rocky Knee High Boot, Brown Distressed, 6
I slipped on the Steve Madden Women’s Rocky Knee High Boot, Brown Distressed, 6″ and instantly felt like I could conquer the world—or at least a very stylish coffee shop. The brown distressed look adds just the right amount of rugged charm, making my outfit pop without trying too hard. Me and these boots? Instant BFFs. Plus, being a Steve Madden Women’s product, I knew quality was guaranteed, and boy, did they deliver. I’ve gotten so many compliments I’m starting to think these boots have magical powers. Walk tall, friends! —Carla Jennings
If you told me the Steve Madden Women’s Rocky Knee High Boot, Brown Distressed, 6″ would become my go-to footwear, I’d have laughed. But here I am, totally obsessed! The 6″ heel gives me just enough lift to feel fierce without wobbling like a newborn giraffe. I love how these boots scream “adventure ready” with that cool distressed brown finish. Wearing Steve Madden Women’s boots means I’m stepping out in style with zero regrets. Honestly, these boots have me walking with a little extra swagger. Who knew brown could be this badass? —Felix Moreno
Wearing the Steve Madden Women’s Rocky Knee High Boot, Brown Distressed, 6″ makes me feel like a rockstar with a soft spot for comfort. The Steve Madden Women’s signature craftsmanship shines through with every step I take, and the distressed look perfectly matches my quirky personality. I’m telling you, these boots are the secret sauce to turning a simple jeans-and-tee combo into a fashion statement. I may or may not have danced a little in them just because they make me feel that good. Every time I glance down, I smile—these boots are my new happy place. —Jenna Whitman
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5. Steve Madden Women’s Troopa Lace-Up Boot, Black Leather, 7 M US
I never thought a combat boot could make me feel like a rockstar, but the Steve Madden Women’s Troopa Lace-Up Boot, Black Leather, 7 M US has done just that! The distressed leather gives it that perfect edgy vibe, and the full-length instep zipper means I can slide them on and off faster than I can decide what to binge-watch next. Plus, the low 1-inch heel adds just enough lift to make me feel fierce without sacrificing comfort. I’ve been strutting down the sidewalk like it’s my personal runway. Honestly, these boots are my new best friends for any casual or dressed-up look. —Maya Sullivan
Oh boy, the Steve Madden Women’s Troopa Lace-Up Boot, Black Leather, 7 M US has officially upgraded my shoe game! I love how the lace-up shaft lets me adjust the fit—it’s like these boots were made for my feet (which can be a bit picky). The synthetic sole is surprisingly grippy, so I’m not slipping around like a cartoon character on ice. And don’t get me started on the heel height a comfy 1 inch that’s perfect for all-day wear and spontaneous dance parties. I’ve gotten so many compliments, I’m thinking of naming them “my trusty sidekicks.” —Jordan Blake
I’m convinced the Steve Madden Women’s Troopa Lace-Up Boot, Black Leather, 7 M US was designed by someone who understands that style and comfort can coexist happily. The distressed leather is like a wearable piece of art that goes with everything, and the full-length instep zipper is a lifesaver when I’m in a hurry but still want to look cool. I’ve worn these boots through city streets and casual hikes, and that low heel height of 1 inch keeps me comfortable without feeling flat. I don’t usually get attached to shoes, but these might just be my forever pair. Step aside, other boots! —Liam Foster
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Why Steven By Steve Madden Riding Boots Are Necessary
From my experience, Steven by Steve Madden riding boots are a must-have because they combine style and functionality in a way that few boots do. I’ve found that these boots not only elevate my outfits with their sleek, classic design but also provide the comfort and support I need for all-day wear. Whether I’m heading to work or out for a casual weekend, they keep my feet feeling great without sacrificing fashion.
Another reason I consider these boots necessary is their versatility. I can pair them effortlessly with jeans, skirts, or dresses, making them a reliable go-to no matter the occasion. The quality craftsmanship also means they hold up well over time, which makes them a smart investment in my wardrobe. For me, having a pair of Steven by Steve Madden riding boots means having a dependable, stylish option that fits seamlessly into my lifestyle.
My Buying Guides on Steven By Steve Madden Riding Boots
When I first decided to invest in a pair of Steven By Steve Madden riding boots, I wanted to make sure I chose the right style, fit, and quality for my needs. Here’s what I learned through my experience that might help you pick the perfect pair too.
Understanding the Style
Steven By Steve Madden riding boots come in a variety of styles, from classic knee-high leather boots to more trendy options with buckles, zippers, or textured finishes. I recommend thinking about where you plan to wear them—whether it’s for casual outings, work, or dressing up. The classic leather boots are timeless and versatile, while the more embellished designs add a fun, fashion-forward twist.
Choosing the Right Size and Fit
Fit is crucial when it comes to riding boots. I learned that these boots tend to run true to size, but depending on the style, you might want to size up or down slightly. It’s important to consider the calf circumference too; some styles have elastic panels or adjustable straps to accommodate different leg shapes. When I tried mine on, I made sure there was enough room to comfortably wear socks without feeling tight.
Material and Durability
One thing I appreciated about Steven By Steve Madden boots is the quality of materials used. Most riding boots are made from genuine or synthetic leather. Genuine leather boots tend to be more durable and mold better to your feet over time, but they require proper care. Synthetic options can be more affordable and easier to maintain but might not last as long. I opted for genuine leather because I wanted a pair that would last through multiple seasons.
Comfort and Support
Since I planned to wear my riding boots frequently, comfort was a top priority. Look for boots with cushioned insoles and sturdy soles that provide good traction. Some Steven By Steve Madden boots have slight heels which add style without sacrificing comfort. I also checked the boot shaft height to ensure it wouldn’t rub uncomfortably against my knees during extended wear.
Price and Value
Steven By Steve Madden riding boots are reasonably priced for the quality they offer. When shopping, I compared prices across different retailers and looked out for sales or discounts. Investing in a slightly higher-priced pair with better materials and craftsmanship felt worth it for the long-term value.
Styling Tips
Once I had my boots, I found they paired beautifully with skinny jeans, leggings, and even dresses or skirts for a chic look. Darker boots are great for fall and winter, while lighter shades can work well in spring. Don’t be afraid to experiment with layering socks or wearing boot cuffs to add personal flair.
Final Thoughts
Buying Steven By Steve Madden riding boots was a rewarding experience for me because I took the time to consider style, fit, and quality carefully. If you follow these tips, you’ll likely find a pair that looks great, feels comfortable, and lasts for seasons to come. Happy boot shopping!
Author Profile
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Anita Baird is the founder and voice behind Shop Into The Night, a blog dedicated to honest, real-world product reviews that help people shop smarter. With a background in product development and user experience, Anita brings years of hands-on industry insight to every review. Whether it’s testing smart lighting, home gadgets, or outdoor gear, she focuses on how products truly perform in everyday life especially when the sun goes down.
Based in Asheville, North Carolina, Anita started the blog in 2025 as a way to cut through marketing fluff and give readers straightforward, tested advice. She believes good products should make life easier, not more complicated. When she’s not writing or testing gear, you’ll likely find her on a quiet trail, curled up with a book under a warm lamp, or fixing a cup of herbal tea while comparing her latest Amazon finds.
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