6 Late Summer County Fair Outfits to Rock Your Red Cowboy Boots
Late summer is the perfect time for county fairs - think warm days, fun rides, and, of course, all the deep fried treats you can eat. And nothing says “county fair ready” quite like bold red cowboy boots. I styled six fun outfits around my favorite pair to show you how versatile they can be, whether you’re riding the Ferris wheel, snacking on deep fried Oreos, or snapping cute Instagram pics.
Red cowboy boots aren’t just eye-catching, they’re practical, durable, and bring an instant festival vibe. They pair effortlessly with denim, skirts, and dresses, adding a pop of color to every look. Plus, they’re perfect for stomping around the fairgrounds in style.
And fun fact - I’ve actually owned a pair of red cowboy boots almost my entire life, starting with a tiny pair I wore ALL the time when I was about 5. I vividly remember kicking my sister in the shin with them - sorry Stacey, love you! I bought the pair in these photos in 2008. They were already vintage, being sold in a boutique that one of my friends was doing her college internship at. I can’t believe that was 17 years ago!
Outfit 1: Denim Mini Dress with Western Accessories
This denim mini dress outfit is a perfect late summer county fair look with red cowboy boots and western accessories.
Channel classic Western vibes with a denim mini dress paired with your red cowboy boots. Add a statement western-style belt to cinch the waist and a coordinating hat for extra flair. This look is playful and flattering and the bold boots tie the outfit together, making it festival-ready from head to toe.
(Red cowboy boots: thrifted in 2008; these have high ratings and have sold over 4k // Denim dress: Zara // Handbag: thrifted Kelly inspired crossbody bag; similar here // Double buckle belt: Amazon 2020, no longer available; similar here // Hat: old, TJ Maxx; similar here, here and here - Claudia used to intern for me ages ago and now she makes truly beautiful hats, check them out and her bio! She is amazing! // Ring: Marc Jacobs daisy perfume ring)
Outfit 2: Denim Skort & Statement Shirt
This eyelet shirt is a great feminine piece to pair with a denim skort!
For a fun, playful vibe, match a mini skort with a fun top, like this eyelet one. Add a statement belt or accessories to tie the look together for the perfect fair photos next to the Ferris wheel or a cotton candy stand.
(Top: old Zara; similar here // Skort: Zara)
Outfit 3: Casual Denim, Tank & Flannel
Keep it cool and effortless with classic denim shorts or jeans (or in my case, a denim skort!), paired with a simple tank top. Add a flannel shirt either worn or tied around your waist, for an easy, laid-back vibe that screams “this isn’t my first county fair!” This outfit is comfortable, practical, and gives your red cowboy boots center stage without overdoing it. Bonus: tie the flannel around your waist for photos or wear it if the evening turns chilly.
(Tank: Uniqlo bra top - I couldn’t find it online but I collect their bra tops because they are truly the best. Here’s the link directly to all of their bra tops. // Flannel: thrifted, similar here with great reviews but check your local thrift shops first and don’t forget to check the men’s section! // Sunglasses: local find; similar here)
Outfit 4: Patterned Dress with a Pop of Red
Lightweight printed dress with red cowboy boots screams understated sexy!
Pair a breezy printed dress with your cowboy boots for a flirty, feminine vibe. Perfect for enjoying live music at the fair or indulging in a funnel cake without worrying about ruining your look. Add a red lip to tie in the cowboy boots! P.S. the slit on this Massimo Dutti dress is what sold me - it’s understated sexy and it’s only noticeable when you walk.
(Dress: Massimo Dutti // Bag: Saint Laurent Emmanuelle small fringed bucket bag, vegan faux suede leather option here - someone in the review added a gold chain strap to it which is totally inspiring me!)
Outfit 5: Casual Denim & Red Boots
These red cowboy boots pair perfectly with casual denim and deep fried fair snacks.
A classic choice—denim shorts and a simple tucked-in tee or blouse. This combo keeps you cool and comfortable while letting your boots steal the show. Add a wide-brim hat for extra sun protection and style points.
(T-shirt: Rebellious One graphic tee from the BX // Denim shorts: thrifted)
Outfit 6: Layered Look for Cooler Evenings
Love that the red in the sweater ties in with the red cowboy boots.
Late summer evenings can get a little chilly. Throw on a casual dress with a denim or utility jacket. Your red boots will keep the outfit lively and bright, even as the sun goes down.
(Sweater: thrifted; Jeans; Zara, couldn’t find them online but they are recent!)
There you have it - six fun, festival-ready outfits all starring my trusty red cowboy boots. Whether you’re strolling through corn mazes, snapping photos with giant stuffed prizes, or indulging in fair snacks, these looks will keep you stylish and comfy all day long.
Which outfit is your favorite? Comment below and share your county fair style tips!
