Now that Labor Day weekend is behind us, it’s time to say goodbye to summer and hello to fall. As we’re crafting that perfect autumnal wardrobe, it’s important to secure some staples that will unfailingly pair well together in any look– specifically, boots and denim.

Whether you want short and chunky ankle boots or some over-the-knee riding boots, cropped flare or baggy jeans or mom jeans, make sure you can style your wardrobe endlessly and interchangeably this fall to maximize your fashion potential. 

Trying to channel the powerful energy of Ariana Grande all through the coming fall season? Try her classic thigh-high suede boots worn over a pair of super flattering skinny jeans. Looking to ease your way into a wider-leg jean? Some statement ankle booties will make the transition a lot less daunting and a whole lot more stylish. Are you looking for a pair of boots made for walking? Something with little to no heel like a sleek and simple Chelsea boot might be right for you, and luckily it goes with practically every pair of jeans on this list. 

Whatever your style, there’s a pair of boots and jeans that are perfect for one another (and you) just waiting to elevate your fall wardrobe. Here are 24 boots and jeans that look great together.

Straight Leg Jeans

Straight leg jeans can cause quite the conundrum when it comes to selecting a style of shoe to match, but sock-style booties are a sleek and simple solution. Form-fitting ankle booties will slide right under them hem of straight leg jeans with ease.


Skinny Jeans

Skinny jeans are the perfect opportunity to break out the knee-high boots for maximum coziness and maximum style. 

Baggy Jeans

Baggy jeans definitely warrant an extra chunky boot to complete the 90’s grunge-inspired look. 

Cropped Ankle Flare Jeans

Cropped ankle flare jeans, while adorable, leave quite a bit of ankle space out in the open. That’s where mid calf booties come in– fill that bare ankle space with a bold pattern that makes a stylish statement. 

Flare Jeans

Jeans with an extra bit of flare in the leg open up a world of possibilities when it comes to boots. A cowboy-inspired boot gives a proper nod to the bootcut style, while a uniquely patterned ankle bootie peeping out from underneath a wide leg is sure to be a fierce fashion hit, and you can truly never go wrong with a Chelsea boot. 

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