riding boots outfit

New Ways on How To Wear Riding Boots With Your Wardrobe in 2024

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As the sun rises on a fresh new year, we often crave to spice up our wardrobes with something new. Much like fashion trends, shoe styles ebb and flow like the ocean tides. What’s considered the hot trend one moment can quickly fade away the next, but the real gems are the ones that stand the test of time, emerging through every fashion tide looking even more stylish. Riding boots, though seemingly outdated to some at present, fit that description perfectly.

Now, if you’re sitting there wondering if those dusty riding boots sitting in your closet can come in handy again, you’ve come to the right place! It’s time to shed some love on this often-overlooked piece of footwear. Sure, they might not currently be stealing the spotlight on every fashion runway or being toted as the “must-have” shoes of the season, but these enduring classics have their unique charm.

Over the years, I’ve shown you how to wear everything from knee-high boots to cowboy boots to ankle boots, but the style of boot to consider wearing again for 2024 is nothing new – it’s the humble riding boot. Below are 8 outfit ideas that will make you love riding boots as much as I do. You might even start wearing them more than your short boots!

1. wool coat + black leggings + oversized sweater + hoop earrings

how to wear riding boots

coat | sweater | boots

One of the easiest ways to style riding boots is with leggings. They’re very easy to tuck in the boots, creating a sleek and streamlined look. As a bonus, black leggings that match black riding boots can offer a very coordinated finish.

As for the top, I layered my camel belted wool coat over a grey oversized sweater for a preppy autumn style. I kept my accessories simple and chic by popping on hoop earrings for a put-together finish. Sometimes simple jewelry is best.

Doesn’t the overall look scream “chic countryside”? Just picture yourself wearing this outfit while you pick apples on a cold autumn day or stroll through the city of London on your next adventure.

Who This Outfit Is Ideal For: This first outfit is perfect if you want to switch up your usual leggings and sneakers. The riding boots will instantly dress up your leggings and make your outfit look more expensive. This outfit idea is also great for anyone who loves a cozy yet chic style.

2. checked blazer + checked mini skirt + white button-down + long socks + black oversized sunglasses

riding boots outfit

blazer | skirt | top | boots

For a super chic look, you can never go wrong with a coordinating set, especially in a timeless print. The coordinated set exudes an effortless elegance, while the checked or plaid pattern never goes out of style.

I offset the print with a white button-down shirt to keep my look balanced. The shirt also helps to maintain the sophisticated appeal of the blazer and skirt set.

I teamed up the outfit with black riding boots to take the look to a whole new level. For a layered look, riding boots pair perfectly with long white socks for a preppy finish!

Who This Outfit Is Ideal For: If you have been wearing heels with your blazers and skirts in 2023, and you want to embrace a different style in the new year, try riding boots. They are equally timeless and can offer an elevated look too. This outfit idea is also great for transitional dressing. A blazer mini skirt and riding boots are perfect for those in-between-season days when it’s not too cold or hot.

3. black blazer + oversized sweater + leggings + sunglasses + belt + earrings

how to wear riding boots

blazer | sweater | boots

Wondering how to wear riding boots in a modern way? The answer lies in an oversized blazer. The classic combo of a blazer and boots is a surefire way to nail chic winter dressing.

And although most people consider leggings indoor lounge clothes (I do too sometimes), they can be worn sophisticatedly with riding boots with a long enough top – and an oversized blazer is perfect for this.

For a smart layered look, wear your blazer over an oversized sweater. To stop the outfit from looking frumpy, team it up with a black belt to accentuate your waist and give your look some visual appeal.

As for the accessories, follow the black color scheme of the outfit by popping on black oversized sunglasses for a cool look.

Who This Outfit Is Ideal For: This third look is a fail-safe way to cool winter dressing. Do you plan to have brunch with your best friends? Why not try this classy outfit? It’s also ideal for anyone who loves “cool” and (slightly) trendy outfits.

Do you need more fall and winter outfit ideas? I have a free Classic Fall Capsule Shopping List for you – sign up here to get the list!

4. jacket + leggings + quilted bag + sunglasses

riding boots outfit

coat (similar) | boots

A jacket in a cozy fabric is perfect for creating a winter outfit you’ll want to wear all season long. Take your oversized fall or winter jacket and pair it with sleek black leggings for a fitted finish.

Accessorize your posh winter outfit with a quilted bag and black oversized sunglasses for a flawless look. Go the extra mile and rock a red lip to make your outfit stand out!

Who This Outfit Is Ideal For: Do you want to look like a “rich wife” at a fancy ski resort? This outfit has your name all over it. The neutrals, simplicity, and class of the clothing items will help you achieve that aesthetic.

5. black shorts + white turtleneck + blazer + sheer black tights

riding boots outfit

blazer | shorts | turtleneck | boots

Leggings and skirts are not the only bottoms that look perfect with riding boots. Try something different and opt for a classic pair of shorts! They are a great way to show off your shoes (and legs – if that’s your thing). Add an extra dose of glamour to the shorts by pairing them with black sheer tights.

I opted for a white turtleneck to brighten up my outfit for a balanced look. The turtleneck is also a perfect top for dressing in cold weather. And, of course, I had to complete my look with black oversized sunglasses for a cool finish!

Who This Outfit Is Ideal For: It’s perfect if you need a fashionable work-inspired outfit for transitional dressing, grabbing lunch, or going on a coffee date.

6. sweater + black skirt + scarf + sheer black tights

riding boots outfit

sweater | skirt | boots | scarf (similar)

Do you like slightly trendy looks? Then this outfit is worth copying and saving to your Pinterest fashion board!

Any mini black skirt works when it comes to learning how to wear riding boots. The shorter length gives the boots an update, while the sheer tights elevate your outfit and add additional coverage.

The oversized scarf adds that current and trendy accessory and complements the other neutrals in the outfit.

Who This Outfit Is Ideal For: Are you looking for the perfect late spring or early fall outfit? This cozy and chic look is what you need to stand out in style.

7. trench coat + jeans + white button-down shirt + black sunglasses

how to wear riding boots

coat | shirt | boots

A trench coat is a longstanding fashion staple and I can always rely on it to create the best looks. So, of course, I had to use it when styling my riding boots!

I layered my khaki hue coat over a white button-down shirt for an instant chic look. Next, I paired skinny jeans with my boots because skinny jeans are easy to tuck in. To complete the outfit, I accessorized with my trusty sunglasses and gold hoop earrings.

Simple, easy, and timeless. Those are the best looks!

Who This Outfit Is Ideal For: This is a great outfit option if you are looking for a sophisticated daytime look to rock for casual days.

8. striped cardigan + white button-down shirt + black skirt + tights + bag

riding boots outfit
How to wear riding boots

cardigan (similar) | top | skirt | boots

Doesn’t this third outfit idea just scream old money? It is so effortlessly classy and oozes an expensive look. I layered on a white and black striped cardigan over a white button-down for a simple and elegant look.

Next, I accompanied the layered tops with a black skirt and sheer tights to give the outfit the right amount of elegance and fun.

Who This Outfit Is Ideal For: Plan on going on a lot of date nights with your significant other in the new year? This look is the perfect evening outfit idea.

Reasons To Wear Riding Boots in 2024

If you are still not convinced to add riding boots to your 2024 closet, here are some reasons that changed the way I view riding boots. Because if I’m being honest, I was curious too whether they could work with my style or not. Would they make me look like a horse rider? Would the boots make my outfit costume-y? Or dated?

Thankfully, after playing around with a wide variety of pieces in my wardrobe, I’ve discovered that it’s possible to give riding boots a fashionable and modern update.

Classic style: As you all know, I am not a big fan of fashion trends. I like my clothes to endure fashion cycles because it saves me money from constantly updating my wardrobe. So it didn’t take a long time for me to realize that riding boots align with my fashion taste. They have a classic appeal that transcends fashion trends.

If you also have a timeless and enduring fashion aesthetic, I recommend giving this shoe style a try!

Versatility: I love footwear that can work well with a wide variety of looks – it makes it well worth the purchase. Thankfully, riding boots are very versatile. I can easily dress them up with a skirt or a black blazer or dress them down with leggings. They’re also great when paired with my long socks and tights.

Equestrian elegance: The equestrian-inspired design of the classic riding boot can be elegant and chic. The clean lines and sturdy structure contribute to the refined appearance. The design makes it perfect for instantly elevating all my ensembles from ordinary to fancy. 

Good quality materials: I don’t only put much attention into the look of shoes but also how they’re made. You can find riding boots made out of high-quality leather, ensuring durability and the ability to wear them for many years.

And once you find a pair you love in one color you can get them again in a different color to shake up your wardrobe. Perhaps brown next time?

Seasonless appeal: Did you know these boots can work well for any season? Yes, including summer! Though it’s true that riding boots are perfect for the winter months. They look amazing for cold weather dressing and pair effortlessly with cozy sweaters and coats.

Spring is also a great season for rocking riding boots. You can pair them with a flowy dress, breezy skirts, and cardigans.

Fall is the ultimate season for wearing riding boots as they perfectly pair with skinny jeans, trench coats, and layered outfits.

And for summer? You can style them with some shorts for a chic and casual look.

Riding boots are perfect for all-year fashion!

Different occasions: Another reason riding boots are a good option is because you can wear them for many occasions. About to run errands? Grab riding boots. Date night with husband? Throw on riding boots. Brunch with gal pals? You guessed it: Grab your riding boots! They’re sleek and comfortable, bringing me to my next point.

Comfortable design: Thanks to the flat heel, riding boots can be one of the most comfortable boots you’ll wear. The boots are sturdy yet comfortable, which makes them practical while maintaining a chic appearance.

Timeless investment: A pair of high-quality boots can be one of your best fashion investments. They’re durable and will remain in style year after year. (Style and fashion are different, by the way.)

Key Tips for Styling Riding Boots:

Keep it simple: When it came to styling my riding boots, I made sure to keep my outfits simple. I stuck to clean lines and versatile designs that are tried and tested.

Stick to neutral colors: White, black, grey, and beige clothing items played an important role in styling riding boots. They are complementary colors, so it made styling my boots very easy.

Incorporate a lot of classic designs: Riding boots look effortlessly chic when they are worn with classic designs. Avoid styling them with too many fads to try to give them an updated look, though a contemporary piece or two can certainly help bring the overall outfit into today’s fashion!

Accessories are your friend: Riding boots have a simple yet timeless appeal. To maintain the sophisticated aesthetic with accessories that are equally as classic, I recommend oversized sunglasses, a scarf, tights, and a quilted bag.

A good makeup look: Learning how to wear riding boots involves not only wearing the right clothes but also focusing on your makeup. Opt for classy makeup like bold red lipstick or lip gloss, and go for a foundation with a skin-like finish. These details will match the elegant appeal of the riding boots.

An effortless hairstyle: Don’t forget your hair! Try effortless and classy hairstyles to go with the fancy aesthetic of your riding boots.

Wear your boots with confidence: To pull off the riding boot style, you need to wear them with confidence!

Learning how to wear riding boots in a modern and chic way is easier than you think. With classic and versatile clothes and accessories, as well as a neutral color palette, you will become a pro at styling riding boots in no time!

We’re still in the winter season, aka, “boot season,” so this next post will help you master the styling of boots with jeans. Up Next: Your Guide on How To Wear Ankle Boots (and More) With Jeans, Plus Tips for Always Getting It Right


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making mychicobsession.com a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.