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Quick! What’s your hardest-working accessory for the fall and winter seasons? If you thought of boots, then ding ding ding! You are in the right place. From ankle to cowboy to over-the-knee, the versatility of a good can take an outfit the extra mile. Yet, there’s one style that has stood the test of time and trends—the riding boot. A perfect knee-high boot that combines traditional design and comfort for a style that still feels fresh season after season, the riding boot is your fall-season companion.
While the riding boot is steeped in a more classic style, it’s anything but blah. Playing with proportion, and differing lengths in jackets and pants, a pair of riding boots can transform an outfit or be the missing piece in your look. From downtown cool to street style-meets-prep, the riding boot fits snuggly into a diverse set of fashion profiles.
For a refresh and re-education in wearing these knee-high boots, we’ve pulled together 10 ways a pair of riding boots can complete your look.
Tuck Your Jeans In
Tucking your jeans into your boots may not be a new style trick, but with this season’s wide-leg jeans trend, you get a brand-new silhouette. Your jeans give off a blouson effect when tucked into knee-high riding boots, which adds subtle interest to your look. To keep your outfit grounded, an oversized blazer keeps with the traditional style of the riding boot for a casual ensemble.
A Cowboy Style
Inject some Western sensibility into your look with a cowboy-style riding boot. After all, both are a nod to horseriding, so have some fun with it! An A-line skirt and colorful top keep your look from veering too hard into the stables with a modern feminine approach.
With a Midi Skirt
Combining two fall favorites, a midi skirt and knee-high boots, equals an outfit made for showing off. A midi skirt has that perfect swingy effect as you walk that contrasts so nicely with a stiff pair of leather riding boots. The perfect mix of soft and hard we love so much in our outfits, you’d be hard-pressed not to smile when wearing a tried and true combination.
With Soft Leggings
Riding boots were originally worn with jodhpurs, tight-fitting and reinforced pants that held up when horseback riding. And while the idea of donning fitted pants with riding boots seems appropriate, these rigid pants are totally lacking in the comfort department. For a similar look without the constraint, leggings make a comfortable and chic alternative. You can dress them up or down with a button-up shirt and blazer or white tee and leather biker jacket. No stiff pants are required!
Shorts and jacket
Just because the temps are changing doesn’t mean you can’t enjoy wearing shorts into the early days of fall. For those perfect days full of sunshine and a light breeze, pairing shorts with knee-high riding boots strikes the balance between fashion and function. Your legs get a little more coverage and you get to show off your styling prowess. A lightweight trench coat is there for you if a chill hits the air.
A Mini Skirt
Similar to shorts and boots, a mini skirt is a great companion for your riding boots. When you need a look that’s dressier than shorts, but still want to keep things comfortable a cozy sweater is the perfect addition. A black leather trench adds a layer of warmth and gives your look cool style points.
Lot of Cargo
Do something unexpected and tuck a pair of cargo pants into your riding boots for a look that nods to the trend’s roots. It’s a great way to show off your boots and wear a pant other than jeans. Lean into the provincial aesthetic with a structured peacoat and cable knit sweater for cozy fall vibes.
With a Casual Suit
Suiting has made a comeback in that it no longer screams office workwear. Seen on countless celebs, a suit vest and matching shorts look even cooler with a pair of riding boots. While your first inclination might be to wear pumps or ballet flats, a riding boot is a fun style surprise. In a way, the riding boot relaxes an already relaxed silhouette that comes off confident and stylish.
With Bermuda Shorts
Bermuda shorts made a big comeback this summer and it’s so easy to wear them into fall so don’t pack them away just yet! The long shorts paired with riding boots give your legs coverage for those cooler days, but the look reads more versatile than just wearing pants. Since the days are getting chillier, a graphic sweatshirt or sweater keeps you warm and looking cool.
Collegiate Prep
Don’t be afraid to fully lean into the collegiate look with a luxe pair of brown riding boots. Skinny jeans and a tweed blazer give off professorial sensibilities while balanced with a baseball cap and graphic sweater. What prevents this look from drifting into stuffy territory is the balance of an oversized jacket and large handbag to give a playful take on the traditional uniform.