Like clockwork, fall always manages to make us reassess our relationship with the world around us. You could blame it on the changing colors of leaves, but in reality, it always has to do with our sudden awareness that it's time to overhaul our closets—sweaters must come out of storage, last year's coat might need replacing, and we definitely need to ditch a few things. That realization can spark two emotional responses in people: excitement and/or anxiety. Yes, transitioning your wardrobe into a new season allows you to get creative with your clothing. On the other hand, choosing what trends to adopt, what to buy, or what to wear can be a stressful process, even for the most stylish people. But what if we told you there was no need to put so much pressure on the process?
The easiest place to start is from the ground up, quite literally. While there's no shortage of investment-worthy shoes, for brevity, we've chosen to focus on one style that fashion people are spotted wearing season after season: riding boots. Without fail, these boots manage to gallop back into relevancy every year because of their functionality, versatility, and timeless silhouette. Of course, that's not to say that this style hasn't been perceived as "stuffy" at times, but with the proper styling, it's proven to be a solid staple that can make your transition into the new season a walk in the park.
In the vein of proving just how vital these boots are to navigating cold-weather dressing, we scoured the worldwide internet to round up 21 riding-boot outfit ideas. Plus, we shopped out the key pieces you'll need to re-create each look for yourself to remove some of the work required to transition your wardrobe. Whether you're just curious about how to style riding boots or want simple ways to look stylish throughout the fall and winter, we've got you covered.
WEAR: Scarf Coat + Crossbody Bag + Sweater + Leggings + Riding Boots
Styling Notes: One of the perks of opting for riding boots over any other type of footwear? They elevate even the most "casual" items. Case in point? The outfit above. You can dress up your leggings by throwing on a coat with a built-in scarf, a crossbody bag, and riding boots.
Meet the coat that's made for the Toteme fan girls with a tight budget.
It's never a bad idea to stock up on leggings!
So sleek!
WEAR: Sunglasses + Leather Jacket + T-Shirt + Waistcoat + Miniskirt + Riding Boots
Styling Notes: Another reason this footwear is so popular with the fashion set? Functionality. Unlike other styles, riding boots can easily be paired with just about any staple. For example, the waistcoat you wore throughout the summer can feel fall-forward simply by pairing it with a miniskirt, leather trench coat, and riding boots.
Aritzia's trench is sublime.
PSA: Waistcoats are something you can wear year-round, not just in the summer.
Of course, Tory Burch would create the perfect pair of riding boots.
WEAR: Light Jacket + Mock-Neck Top + Shorts + Tights + Riding Boots + Handbag
Styling Notes: Not to sound like a broken record, but these boots can help you transition some of the warm-weather items in your wardrobe into the colder months easily. Take a cue from the look above by pairing your favorite shorts with a sweater, light jacket, tights, and riding boots.
Nothing screams "old money" like a camel cashmere turtleneck.
Sheertex's tights are worth every cent.
Mango never misses a beat.
WEAR: Sunglasses + Knit Polo + Moto Jacket + Leather Bermuda Shorts + Riding Boots
Styling Notes: Although riding boots have long been associated with preppy fashion aesthetics, you can make them feel a bit more trend-forward with creative styling. Try pairing this footwear with a leather moto jacket, leather shorts, and cool shades for an edgier take on these timeless boots.
Moto jackets are still having a moment (and we're not mad about it).
Opting for leather shorts will ensure you can show off your riding boots.
The hardware detail on these adds just the right dash of edginess to this otherwise traditionally "preppy" footwear.
WEAR: Double-Breasted Coat + Chunky Cable-Knit + Jeans + Riding Boots + Woven Handbag
Styling Notes: If you're more of a minimalist, a more modest way to up the ante of these boots is with color-blocking. Rather than matching with your riding boots, opt for a coat in a contrasting color with a mismatched cardigan styled over it. Playing with colors will allow your boots to pop without doing too much.
I am happy to report this coat is well worth the space in your wardrobe.
Just think of all the ways you can wear this handbag!
These dark-brown riding boots are divine.
WEAR: Blazer + Crewneck Sweater + Skinny Jeans + Riding Boots + Handbag
Styling Notes: For those who can't possibly fathom wearing more than one color, don't fret. Rather than playing with multiple hues, just pick one to incorporate into your signature all-black looks this fall. A black blazer, sweater, skinny jeans, and riding boots can feel "colorful" simply with the addition of a contrasting cardigan and handbag.
Black blazers can be worn year-round.
Layer this cardigan over your shoulders to nail the equestrian-inspired look.
Great boots at a good price point. Need we say more?
WEAR: Dainty Earrings + Tie-Up Top + Baggy Jeans + Riding Boots
Styling Notes: Let's be honest: Styling knee-high boots can be challenging, especially when choosing the right denim to wear with them. While most might opt for skinny fits, if you're not a fan, draw inspiration from the look above. A more straight-leg or baggy jeans tucked into riding boots with a tie-up top can give off saddle-girl energy.
Cottagecore, but make it chicer.
Every ranch-ready look includes a great pair of jeans.
You'll live in these boots.
WEAR: Sculptural Earrings + Bomber Jacket + Sweater + Culottes + Riding Boots
Styling Notes: An additional alternative to skinny jeans? Culottes. If you can't possibly will yourself to squeeze into a pair of skinny jeans this winter, this breezier bottom is the solution to showing off your boots. And if you're worried these pants aren't "cool," simply take inspiration from the look above and pair them with sculptural earrings, a sweater, and a worn-in leather bomber jacket.
These dome-shaped earrings will elevate all your ensembles.
The worn-in effect makes this vegan-leather bomber look designer.
Toteme's riding boots are at the top of our wish list.
WEAR: Shoulder Bag + Chunky Turtleneck Sweater + Miniskirt + Riding Boots
Styling Notes: When in doubt, the simplest way to style these boots is to forgo pants altogether. Try pairing a simple black miniskirt with an oversize turtleneck, shoulder bag, and riding boots for an easy (yet elegant) way to wear this footwear.
So cozy.
Insider hack: Shop for skirts made from wool blends to be able to wear them during the winter months.
The lug sole on these boots ensures they won't slip while walking in winter storms.
WEAR: Sunglasses + Trench Coat + Striped Top + Leather Shorts + Tights + Riding Boots
Styling Notes: When it comes to these boots, you really don't have to do too much for them to look good. In fact, they look best when paired with other basics—e.g., the outfit idea above. Try styling your riding boots with a trench coat, striped top, leather, and shorts for a simple yet utterly stylish fall ensemble.
Trench coats are meant to be worn with riding boots.
Never has a top been more French-coded.
Considering Ralph Lauren's long history of drawing from equestrian apparel, these boots are the ideal investment.
WEAR: Longline Coat + Knit Dress + Riding Boots + Structured Handbag
Styling Notes: Again, the beauty of these boots is that they really do the heavy lifting of elevating any fall look. Rather than focusing on getting overly creative with your styling, make the focal point of your outfit fabulous accessories. Riding boots can really shine when paired with a well-crafted structured handbag and a longline coat.
NGL, I think about this bag on a daily basis.
Longline coats will be in well into the new year.
Jimmy Choo just gets it.
WEAR: Long Wool Coat + Crewneck Sweater + Matching Skirt + Riding Boots + Woven Handbag
Styling Notes: Anyone who lives in a colder climate is acutely aware that once temperatures drop, so does the desire to dress up. If it's freezing out, all you want to wear is the coziest possible 'fit—thankfully, riding boots are up for the task. Pairing this boot style with a matching sweater set, long coat, and woven handbag will ensure you're as cozy and chic as possible.
Aritzia's coats are arguably the best on the market.
Don't forget to buy the matching sweater ($680)!
Three words: Hermès riding boots.
WEAR: Shaggy Fur Coat + T-Shirt + Cardigan + Pleated Miniskirt + Riding Boots + Mini Bag
Styling Notes: For the maximalists reading this story, consider this your sign that riding boots can be incorporated into your wardrobe, too! Sure, this footwear is a bit "simpler," but that can change when styled with a few statement items. You can make this staple shoe stand simply by pairing it with a shaggy fur statement coat and logo-adorned mini bag.
We wouldn't judge you if this shearling coat has you salivating.
Oh, she's cute.
The curved top of these boots is super chic.
WEAR: Chunky Necklace + Maxi Sweaterdress + Riding Boots
Styling Notes: As mentioned before, color can transform these boots from "plain" to punchy—a point proven by the outfit above. Pairing your riding boots with a vibrant maxi sweaterdress and chunky chain necklace is a surefire way to make this staple footwear go the extra mile.
Just what your knitwear has been missing.
Hot, hot, hot.
Your search for the perfect wide-calf boot is officially over.
WEAR: Sunglasses + Turtleneck + Jumpsuit + Riding Boots + Handbag
Styling Notes: Instead of using bright colors to make these boots feel bold, there's a simpler way to get the same result: texture. Pay attention to materials, as pairing your riding boots with a leather jumpsuit and bag with heavy hardware is just as eye-catching as any brightly colored frock.
This jumpsuit did not need to go this hard.
It's the chain detail for me.
The hardware elevates these boots even more.
WEAR: Sunglasses + Oversize Leather Coat + Shoulder Bag + Shirtdress + Riding Boots
Styling Notes: It's worth reiterating: Playing with color and texture can make these boots feel less timeless and more trend-forward. Even the brown riding boots in the back of your closet can feel brand-new again simply by pairing them with a matching oversize leather coat, shirtdress, and contrasting colorful green bag.
Proof that chic coats don't have to cost a fortune.
Forget the search for greener pastures when you can just get this cute bag.
Giddyup.
WEAR: Sunglasses + Layered Chain Necklaces + Sheer Top + Bralette + Miniskirt + Riding Boots
Styling Notes: Yes, playing with color, texture, and general styling can transform these otherwise traditional boots, but for the risk-takers, it might not be enough. Enter the outfit above into the chat. You can spice up this "simple" footwear by pairing it with chains layered on top of a risqué sheer top finished with a miniskirt and black sculptural shades.
You'll wear these for years to come.
Green not your color? You can also shop this sheer mesh top in 19 other shades.
Not all riding boots have to be flat.
WEAR: Shoulder Bag + Oversize Knit Jumper + Knee-Length Socks + Riding Boots
Styling Notes: While there's nothing wrong with having a little sheer separate moment, it's not exactly cold-weather-friendly. Luckily, there are other options! You can feel just as spicy if you style an oversize knit jumper as a dress and finish off the look with knee-length socks that peek out of your riding boots.
Pro tip: Don't be afraid to size up your jumper to be able to style it as a dress.
As an adult, it now makes sense to me why socks are the most coveted holiday gift.
Give your rainboots an upgrade.
WEAR: Long Scarf + Hoops + Tank Top + Miniskirt + Shoulder Bag + Riding Boots
Styling Notes: One more way you can add a little saucy feel to this otherwise seemly shoe style? Opt for a thin-strap tank top paired with a miniskirt, long scarf, hoop earrings, and shoulder bag. It will honor this footwear's timelessness while still being a tantalizing look all around.
Lean into the equestrian theme by pairing your riding boots with a saddle bag.
Ninety Percent's staples are a worthwhile addition to any wardrobe.
Riding boots are already rich-looking, but the chocolate-brown suede on this pair adds another level of decadence.
WEAR: Sunglasses + Hoops + Oversize Cardigan + Cropped T-Shirt + Shorts + Riding Boots
Styling Notes: Averse to taking risks? We get it. Rather than embracing opaque materials, playing with hemlines, or wearing vibrant colors, dial it back a bit. The beauty of riding boots is that they're meant to feel like you're not caught up in the hustle and bustle of the city (or trends) and instead live on a simple ranch out in the country. Embrace that vibe fully by going cottage-core inspired with your look—pair a chunky knit cardigan with a cropped T-shirt, sleep shorts, and riding boots.
You'll never regret investing in classic frames.
It doesn't get cozier than Naked Cashmere's knitwear.
You can also shop these boots in tan, olive, camel, black, and camel.
WEAR: Sunglasses + Printed Dress + Riding Boots
Styling Notes: Hopefully by now, we've given you enough tips on how to style riding boots. But should you still be indecisive about what to wear, consider this final outfit idea all you need. Whether you're out in the fields or the fragrance aisle at Sephora, you can't go wrong with wearing your riding boots with a printed dress and tinted sunglasses.
Colorful shades will add a cool factor to all your fall outfits.
The floral print on this dress will pair perfectly with riding boots.
The simple silhouette of these boots will allow you to wear them for seasons to come.
This post was originally published at an earlier date and has since been updated.
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