What to Wear with Riding Boots: 5 Stylish Outfit Ideas for Cool Weather
Wondering what to wear with riding boots this season? I’ve got you covered with five stylish riding boots outfits you can easily recreate from your wardrobe.
Thanks to fashion’s love affair with the English countryside (Ralph Lauren, Hermès anyone?), riding boots are trending again. As the favorite tall boot for many, their elevated style and low (or no) heel make them a timeless essential for fall and winter. Throwing them on with skinny jeans was the go-to a few years back. But, with relaxed silhouettes now ruling, how do you style riding boots these days?
In this post, I share five chic riding boots looks for cooler days. Think effortless pairings with jeans, dresses, and skirts, for whatever the day demands. Each includes a simple outfit formula, styling notes, pro tips, and shoppable alternatives, so you can unlock how versatile these equestrian staples really are.
Ready to learn how to style riding boots like a pro? Let’s step in!
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Everyday Comfort: What to Wear with Riding Boots and Jeans (Casual)
Pair your go-to denim with riding boots for effortless cold-weather layering.
Outfit Formula:
- Oversized knit
- Layering turtleneck
- Wide leg jeans
- Riding boots
Styling Notes:
A casual winter outfit is instantly elevated with the added structure of the riding boots. I French-tucked my sweater to add shape while balancing proportions, so my pants (and legs) look the longest while remaining cuffed. A not-so-basic look for weekend errands or relaxed gatherings.
Styling Tip:
Thick structured denim is best for rolling up pant hems and showing off your boots.
Shop Similar:
Playful Pairing: Riding Boots and Skirts
Riding boots with skirts mix playful with classy for a chic transitional outfit.
Outfit Formula:
- Suede midi skirt
- Knit top + matching scarf
- Riding boots
- Tweed jacket
Styling Notes:
For this stylish riding boots outfit, I chose an A-line skirt with enough room for my boots without them catching on the fabric. I matched a collar scarf and knit top for a layered look, while a tweed jacket makes this look perfect for fall outings or a day at the office.
Styling Tip:
Match your boots to your skirt to “elongate” your legs. Layer with thick wool tights for warmth on cooler days.
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Classic Touch: Dressy Riding Boots with Jeans
Elevate denim for work or weekends with refined touches in dressy riding boots.
Outfit Formula:
- Belted blazer
- High neck blouse
- Black jeans
- Riding boots
Styling Notes:
Black jeans get elevated in this smart casual outfit with riding boots. I chose slim, slightly cropped barrel-leg jeans that tuck easily into the boots, with a bit of bunching around the thighs (the only kind I welcome!). The belted blazer and sheer blouse add a modern touch to this effortlessly chic classic.
Styling Tip:
Add a newsboy cap for countryside chic, perfect for outdoor activities. Layer with a turtleneck in winter for added coziness.
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Effortless Elegance: Riding Boots and Dresses
A knit dress (or sleek LBD) teams up with riding boots for a cozy feminine twist.
Outfit Formula:
- Knit dress
- Cardigan
- Riding boots
- Leather shoulder bag
Styling Notes:
I layered a thick wool cardigan over a knit black dress, which I usually style for summer as a tank dress (love a piece that gives multi-season wear!). A fringe hobo bag in faux leather adds dimension and a touch of boho. Chocolate brown riding boots and a gold necklace add unexpected warmth to this all-black outfit–ideal for a cozy work outfit or date night.
Styling Tip:
Pair matching wardrobe essentials, like a sweater and knit skirt, to create a similar look. Add a statement belt to make it personal and define your waist.
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Office Chic: What to Wear with Riding Boots and Pants
Swap ankle boots for an updated take on 50-degree (and below) workwear with riding boots and pants.
Outfit Formula:
- Button-down shirt
- Sweater vest
- Slim Trousers
- Riding boots
Styling Notes:
Equestrian boots provide an updated edge to this layered work outfit with a sweater vest and collared shirt. I used slim trousers that comfortably tuck into the boots for a sleek, polished aesthetic. Contrasting neutrals tie together with a patterned neck scarf for a chic statement.
Styling Tip:
Mix and match neutrals for quick, easy capsule outfits on rushed mornings. Try thick materials, like wool and corduroy, on cold winter days, or lightweight blends for transition weather.
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How To Style Riding Boots for Everyday Chic
The secret to styling riding boots outfits for everyday chic lies in these easy tips:
- Match boots with pants, skirts, or tights to elongate your legs.
- Opt for slim, cropped, or tapered styles, or a wide-calf boot, for easy tucking.
- Layer socks over tights on cold-weather days.
- Maintenance hack: Wipe wet boots down to preserve leather; condition each season for casual wear.
- Invest in quality to instantly elevate your budget pieces (high/low aesthetic)
These outfits will take you from fall to spring, with simple material or layer swaps to suit the weather. Riding boots are one of my favorite wardrobe heroes for their effortless ability to take an outfit from basic to stylish. What’s your favorite boot pairing this season? Let me know in the comments!
