Your Guide to Pairing Jeans with Boots This Fall

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24 Boots and Jeans That Look Great Together

It's taken a few days to get used to it, but it's time to say 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.

Or try this textured sock-like style of shoe for a more unique style.


A little bit of stretch combined with a looser fit around the thigh, this ankle jean is the casual straight-leg style to replace your favorite skinny jeans. 


These booties with a sock-like fit pair perfectly with straight leg jeans.


Tik Tok seems to love these light wash straight leg jeans, grab yourself a pair for spring.



Skinny Jeans

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

Have an Ariana Grande in her sweetener era moment this fall with these over-the-knee suede boots that’ll go great with skinny jeans.


Khloe Kardashian certainly knew what she was doing with Good American’s best-selling pair of skinny jeans. These stylish jeans have a gap-proof waistband and are made with super stretch denim for extra comfort.


This boot, with its subtle crocodile print pattern, brings a fresh take to the classic fall knee-highs.


These skinny jeans from Spanx prioritize a sleek silhouette with a pull-on design and stretch denim that’s made for comfortable motion.


Baggy Jeans

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

Dr. Martens Leona 7-hook boots
Dr. Martens via Amazon

Make a steampunk-inspired statement with these platform boots.


These straight leg, high rise jeans are made from premium non-stretch Japanese denim and have that perfect 90’s inspired look without being too baggy.


These chunky ankle boots are timelessly trendy and totally made to be worn with your best pair of baggy jeans.

$70 AT DSW

These baggy jeans can easily be your go-to for a comfortable and casual denim 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. 

Or try these sleek and bold snake print boots for a fierce fashion choice.


These ultra soft cropped flare jeans are cut with transcend denim that has a leather-like coating and subtle shine for a unique look.


These vegan leather crocodile embossed boots will fill the notorious ankle gap caused by cropped flare jeans with some wild style.


These frayed ankle jeans with a ragged hem and subtle flare add a bit of edge to a classic denim look.


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. 

Balance out that bell bottom with a boldly patterned choice in bootie like these spotted leather ones from Anne Klein.

$80 AT DSW

These flare jeans are unabashedly groovy and a total statement piece for your wardrobe.


These Chelsea boots are endlessly chic and utterly timeless, you can keep them as a staple in your fall wardrobe for years to come.


These wide leg jeans have just a touch of flair to them for those immaculately subtle retro fashion vibes.


These chunky platforms have comfortable and thick block heels and will elevate any style of jeans with total flair.


These bootcut jeans are perfect for anyone who isn’t ready to strut down the street in bell bottoms, but still wants some vintage flair for their ‘fit.


These chic patent tortoise patterned booties have a rounded toe and block heels and will look fabulous peeking out from underneath your flair jeans.


Cowboy boots definitely put the boot in bootcut, these western booties will bring some cowboy flair to your ‘fit with a much shorter ankle cut for convenience.

$65 AT DSW


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