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*2023*What to wear with riding boots?18 wearable combo!

*2023*What to wear with riding boots?18 wearable combo!

Fashion comes and goes, but riding boots are here to stay.

Days have gone by when you can only look poised and elegant in the classic brown equestrian boots.

These days, riding boots are unbelievably versatile to style as they have been redesigned in a wide range of modern designs and body-flattering fits.

From off-duty ensembles to timeless preppy styles, riding boots will never fail to give your look an exquisite sense of stylish twist.

So ladies, if you are ready to embrace their new elements like comfy chunky soles, ahead are the 7 outfit combos to pull off riding boots this season.

Enjoy ladies!


what to wear with riding boots, riding boots outfits ladies
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Feeling casual but want to make it fashionable?

Pair riding boots with skinny jeans just to make you look stylish even in the simplest look.

With knee-high boots, it’s always body-flattering to pair a long shirt or tunic to elongate your figure visually.

For a weekend coffee-run look, pair a chambray shirt with black tights and boots to complete a tasteful look.

For extra sassiness, perhaps it’s time to dig out your leopard print handle bag for a pop of fun.


what to wear with riding boots, riding boots outfits ladies
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For the breezy fall season, it can’t be more autumny to pair a billowy maxi chiffon dress with a pair of sleek brown riding boots.

For an extra layer of warmth, either you top it with an oversized blazer or longline cardigan is equally flattering.

When the days are chilly, the combos with riding boots can be truly endless.

To pull off riding boots in a modern way, pair them with an oversized sweater dress with a pair of retro round sunglasses.

You know, it’s always fun to add some retro flare to the high street look.


what to wear with riding boots, riding boots outfits ladies
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Both inspired by the equestrian theme, preppy fashion, and riding boots are bound to work wonders together.

When it comes to elegant fashion, it’s way more than wearing a long beige trend coat and a classic Chanel bag.

For a timeless posh look, pair the riding boots with a heavy weave oxford shirt and dress pants for a sculpted silhouette.

If you want to glam up the look, add a faux leather belt and a sleek blazer just add a dash of sophistication to your style.

Or else, throw yourself a checked beret to bring out the old days’ charm.


what to wear with riding boots, riding boots outfits ladies
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Want to show some character with your riding boots? Perhaps it’s time to be more experimental with all sorts of sock pairings.

I don’t know about you but sometimes I just feel riding boots look too sharp to wear.

That said, team them with a nice pair of white cable knit thigh-high socks just instantly change to style connotation for the good. It just looks softer with a dash of feminine vibes.

Want to embrace schoolgirl fashion with over-the-knee socks and riding boots?

Let’s complete another Gossip Girl look with a white dress shirt and a mini pleated skirt. (Good old memories, anyone? xo)


what to wear with riding boots, riding boots outfits ladies
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This season, riding boots are making a comeback and it’s not hard to see all these fashionistas wearing them with all kinds of stylish twists these days.

With the latest chunky sole and clean-cut design, the boots themselves just look edgy and boyish in nature.

Whether you pair them with a faux leather biker jacket or an oversized trench coat, this just looks one-of-a-kind.

Among all the looks, my favorite combo is teaming black riding boots with a military jacket. With a sleek high bun and sunglasses, it just looks so. damn. cool.


what to wear with riding boots, riding boots outfits ladies
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Want to look effortlessly chic with minimal effort? While it sounds too good to be true but it’s totally possible if you style them in a monochrome way.

As some of the riding boots can look chunky (especially the one with round toes design), wearing similar hues for the overall outfits can elongate your figure visually and make you look so put-together.

But of course, monotone isn’t about wearing only one color but instead, one color tone.

That said, for a beige monochrome, you can always style beige and dark brown together for a layered look.

To avoid being top-heavy, I will always wear darker shades for the bottom.


what to wear with riding boots, riding boots outfits ladies
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As a petite girl, I must say not every riding boot flatters my body.

Sometimes, I can feel quite overwhelmed with some pairs so here are a few tips to share.

First thing first, always opt for a pointy toe instead of the round toe design as the V-shape can always elongate your legs even more.

I know it sounds not a big deal, but trust me that can make a difference.

Second, always pair your boots and pants with a similar shade.

Even if you are not a fan of the monotone pairing, at least don’t wear your boots and bottoms with contrasting hues as that can visually cut off your leg and make you look shorter. ( Trust me, the result can be brutal.)

As for the dresses, always make sure to allow a peek of your knee area for a flattering effect.

And lastly, if you are extra petite and feel like your riding boots are dragging you know, go for the short boots version – it’s equally fabulous!


So ladies, here are the 7 outfit tips if you wonder what to wear with riding boots. Let’s have a quick recap first.

  • Pair riding boots with jeans for a casual ensemble
  • Wear riding boots with a dress
  • Pull off riding boots in preppy style
  • Pair riding boots with thigh high socks
  • Stay cool in riding boots
  • Go monochrome when in doubt
  • Riding boots tips for petite girls

If you are looking for more styling tips, check out the articles below to unlock some new combos! See you there loves!

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