How to Style Riding Boots: 10+ Outfit Ideas for Every Occasion

The fall season sparks a change in every aspect, including the items you reach for when putting together an outfit. One of my personal favorites? The different types of shoes that can be added back into rotation.

While ballet flats, chunky loafers, white sneakers, and ankle booties are all expected fall shoe choices, there’s one other style that often seems to be left out: riding boots. You might think that knee high boots are an aggressive choice to wear in autumn weather, but the reality is that there are ways you can style them to accommodate both mild temperatures and more tough, winter conditions. This makes a strong case for adding a pair to your closet, since they can be worn throughout multiple seasons, as well as styled for various occasions.

With that being said, I know firsthand that riding boots can be an intimidating piece to start incorporating into your outfits. They typically make a more bold statement and they can feel like they pull a lot of “attention” your look. If you’re a more minimalist dresser, this can seem like a big step outside of your comfort zone — but don’t let it stop you from playing around with this classic staple!

Here, I’m sharing exactly how to style riding boots, whether you’re looking for something cozy and practical or more feminine and flirty.

How to Style Riding Boots

Riding Boots and Denim Shorts

Riding boots often get nixed from the wardrobe lineup when it’s a transitional season. However, if this outfit proves one thing, let it show you that you can easily incorporate tall boots into warm-to-cool weather looks. They’re great to pair with staples like denim shorts, offering a chic and fun look that can be worn from day to night.

Style Tip: For a more casual riding boot outfit, opt for shoes that have a more western feel. These are a tried-and-true favorite that I’ve had in my closet for years (and yes, they are worth the investment!)

Riding Boots and a Skirt

Craving a preppy and polished look? Channel your inner school girl vibes with a mini skirt, riding boots, and a v-neck sweater. This outfit was made for the fall season, but it could also be worn into the winter as well as in late spring. Accessorize with a pair of chunky gold earrings to break up the otherwise monochromatic look.

Style Tip: Make this outfit winter-appropriate by wearing tights underneath the skirt. You could also opt for a long skirt altogether (perhaps a silk slip skirt) if you want more coverage.

Riding Boots and a Sweater Dress

I always say that midi dresses are a practical and cute option to wear throughout all seasons, and coming in a close second would be sweater dresses. You can find everything from lightweight knit dresses to warmer wool and turtleneck styles. Depending on the elements, you could wear a sweater dress on its own or add a layer, like this sherpa jacket (which is such a good Amazon find!)

Style Tip: For an unexpected and well-styled touch, slip into a pair of stockings and have them peek out of the tops of your boots.

Riding Boots and Black Leggings

If the concept of wearing riding boots is on the more intimidating side, this is a greater “starter” outfit option. Not only do the black leggings make it ultra-comfy, but they provide a sleek and versatile base layer that you can pair several tops and accessories with. To replicate this look, opt for a polo sweater as your top of choice (with or without a tank underneath), a tote bag, and some simple black boots.

Style Tip: Wear an oversized sweater or top with leggings to provide more coverage and to ensure that you feel confident when you’re out and about.

Riding Boots and a Wool Coat

This is another cute sweater dress outfit that pairs perfectly with knee-high boots. I’d wear this for anything from brunch with friends to a work meeting. It would also make an on-theme choice to pack for a fall trip to Paris (so chic!) For cooler temps, add a wool coat on top — you could also drape it over your shoulders for a sophisticated and useful touch.

Style Tip: Wearing a belt with a sweater dress not only adds a unique element, but it can also help define your waist and give your look a more flattering shape.

Riding Boot Outfits

Looking for more outfit inspiration? I’ve worn so many riding boot outfits over the years and thought I’d round some of the photos up so you have plenty of options to choose from. As you can see, they pair well with a variety of pieces and can work throughout several seasons.

I hope this post helped you figure out how to style riding boots. If you have any additional ideas, please leave them in the comment section below!