How To Make Cowboy Boots Work With All Your Fall Outfits

While not everyone is a fan of trends coming back, sometimes they can bring about a new modern twist. As we've seen with a lot of trends recently, comeback trends have been remixed to fit with a modern era. Cowboy boots are not an exception in this case.


Although many of us equate cowboy boots with a stellar western Halloween costume, they are coming back in full force. Not just for Wild West black and white movies anymore, cowboy boots are the chicest new footwear trend to hit street style looks. While it may seem like cowboy boots have come out of thin air to appear on our social media feeds, there's nothing surprising about their newfound popularity. Style content creator, Vanessa Chen, tells Nylon, "[These styles] offer a kind of escapism where people can detach and express themselves outside of their current environment or situation. Simply put, people just want styles that are fun, dramatic, and don't take themselves too seriously."

Even though this fun and unique footwear is nowhere near the classic-ness or minimalist of nude pumps, they are a must-have for your fall wardrobe. In the end, the difference between it looking costume-y and chic lies in your styling.


Style with tailored pieces

Everyone loves a good balance. That's why when it comes to styling your cowboy boots, you'll want to go with something opposite to the fun and uniqueness of your boots. Style your boots with tailored pieces to add an aura of sophistication and seriousness to your fall outfit. Although it seems like these two pieces wouldn't make a great pair, they are an unexpected combination you need in your wardrobe this fall.


Sugar Love Chic shows us how a colorful blazer can be the perfect combo with a neutral pair of cowboy boots. Whether you decide to finish this off with a pair of denim jeans or trousers is up to you, but there's no denying this is an exciting match. If you're afraid of cowboy boots overshadowing your look, this is a great way to have them blend in and let your blazer shine.

If you need more inspiration, no need to look further than the style icon that was Princess Diana. Princess Diana was always a fan of styling sports chic with a bit of uniqueness. That's why the late Princess Diana helped elevate her red cowboy boots with an all-white look and dark grey blazer. Finishing off this iconic look was a casual baseball cap. Although all of these pieces separately may not seem to work together, her dark grey blazer brought the look together to create a chic look we all need to recreate.


Wear with a miniskirt

While miniskirts may not be your typical fall attire, they will be one of the hottest items for the season. Whether you add in tights or not, miniskirts and cowboy boots are a pair to keep your eye on. Miniskirts of all varieties are a great option, especially tennis skirts. With the increased popularity of tenniscore, tennis skirts will be everywhere this season. Imani Randolph shows us how a white mini tennis skirt, brown sweater, and matching white cowboy boots are fall outfit must-haves.


Thanks to brands like Miu Miu, ultra miniskirts are going nowhere this fall season. If you want to mix both top trends, take a cue from singer Dua Lipa. Lipa paired black cowboy boots with a matching orange knit set, including a miniskirt. This particular combination will help you elongate your legs even more, and with the help of your cowboy boots, you are ready for a chic fall night.

Grab a shirtdress

Classic dresses in the fall season include sweaters and knit dresses. Instead of pairing your cowboy boots with these classic pieces, opt for a chic shirtdress that will make your cowboy boots look stylish and casual. To elevate your cowboy boots, opt for a matching ensemble. Going with a white shirtdress, white cowboy boots, and a white purse exudes luxury and chicness. Dressing in monochrome is an easy way to elevate your look and make it seem more expensive.


Another way to use a shirtdress to accent your cowboy boots is by styling your shirtdress with accents in the same color as your boots. Like content creator and Gisou founderĀ Negin Mirsalehi, grab a white shirtdress but add touches of brown accessories that will complement your classic brown cowboy boots. While these add more rustic touches to your look, your white shirtdress will keep your outfit elevated and chic. To keep your ensemble appropriate for the changing fall weather, you can also choose to layer your shirtdress with a sweater vest or chunky sweater on top. This will keep you extra warm during the fall season.

Reach for a mini dress

Like with miniskirts, a mini dress is a great way to show off your legs and create some more length. As well, the mini dress and cowboy boot combination is one way that you can take your boots out for a stylish night on the town. Giza Timonier shows off her black printed mini dress, black cowboy boots, and a dark blazer over top as a chic way to take your boots out for the night. This is the perfect way you can also look stylish but add more comfort to your footwear. Depending on the cowboy boots you wear, they can be the perfect alternative to uncomfortable heels.


Another way you can take advantage of these two pieces is by playing with the colors and heights. Although cowboy boots are typically mid-calf in length, @katesusanin shows us how a pair of tall cowboy boots can be just what you need. Instead of your average mid-calf cowboy boots, tall boots take up some of that extra space your mini dress gives you. Still giving you the desired length, tall boots help cover some more skin on an extra chilly night. Kate paired her white boots with a matching white mini-dress, creating a chic monochrome look.

Have fun with all denim

One of the best ways you can have fun with your cowboy boots is by embracing their western nature. Although some want to counteract the western style of cowboy boots, another way to style your boots is by playing off of that style. Vale from Fashion and Cookies shows us how chic a denim maxi dress and cowboy boots combo can be. Vale played up this western chic outfit by pairing a denim maxi dress with her brown cowboy boots with blue detailing. Finishing off her look was a hat, crossbody bag, and sunglasses. Although fully western-style, nothing about this outfit seems gimmicky or like a Halloween costume. Instead, this is a chic way to have a bit of fun with your cowboy boots.


If you want something more street style, @justine___va paired a denim jumpsuit, wide-brim hat, and color-contrasting cowboy boots. Within the western-chic look, this outfit is ready for the runway. Instead of feeling overwhelmed by cowboy boots, both content creators embraced the vibe and went full-western in their attire.