Boots and jeans that look great together

Fashion Photo Session In Paris - January 2021
Thinking of trying wide-leg jeans? For that fashion foray, a funky pattern or chunky ankle boot will help balance out the bold silhouette.  Edward Berthelot/Getty Images

Labor Day weekend has come and gone, which means fall is officially here. Whether that means returning to school, the office or simply preparing for the incoming sweater weather, a solid autumn wardrobe can help ease the transition into this new season. And there’s no better place to start than the fall essentials: a great, reliable pair of boots and jeans.

From chunky ankle boots to a suede thigh-high boot, and from cropped flare jeans to baggy mom jeans, the ease of having interchangeable, stylish staples for the season should never be underestimated. Looking to make those summer skinny jeans last into fall? Try a unique take on the classic knee-high riding boot. Thinking of testing the waters on a wide-leg silhouette? For that fashion foray, a bold mid-calf boot will serve you well.

When in doubt, Chelsea boots pair well with practically everything, and have a timeless style.

With that perfect pair of boots and jeans in your fashion arsenal, this season should be jam-packed with style success. Here are 24 pairs of 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.


90’s ultra high rise straight jeans in light ripped wash

90's ultra high rise straight jeans in light ripped wash
Abercrombie & Fitch

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

90’s ultra high rise straight jeans in light ripped wash, $30 (reduced from $99)


90’s ultra high rise straight jeans in dark wash

90's ultra high rise straight jeans in dark wash
Abercrombie & Fitch

Or let this cool and casual simple straight-leg style replace your favorite skinny jeans.

90’s ultra high rise straight jeans in dark wash, $99


Vagabond Shoemakers MYA stretch bootie

Vagabond Shoemakers MYA stretch bootie
Nordstrom

These sock boots pair perfectly with straight-leg jeans.

Vagabond Shoemakers MYA stretch bootie, $160


Everlane Glove boot

Everlane Glove boot
Everlane

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

Everlane Glove boot, $120


Skinny Jeans

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


Good American Good Legs skinny jeans 

Good American Good Legs skinny jeans
Good American

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.

Good American Good Legs skinny jeans, $99


Spanx ankle skinny jeans

Spanx ankle skinny jeans
Spanx

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

Spanx ankle skinny jeans, $128


Vince Camuto Alimber knee-high boot

Vince Camuto Alimber knee-high boot
Nordstrom

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

Vince Camuto Alimber knee-high boot, $229


So Much Yes black suede over-the-knee boots

Lulus So Much Yes black suede over-the-knee boots
Lulus

Have an Ariana Grande Sweetener-era moment this fall with these over-the-knee suede boots that’ll go well with skinny jeans. 

So Much Yes black suede over-the-knee boots, $58


Baggy Jeans

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


90’s Cheeky jeans

Everlane '90s Cheeky Jean
Everlane

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

90’s Cheeky jeans, $88


BDG high-waisted baggy jeans

BDG high-waisted baggy jeans
Urban Outfitters

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

BDG high-waisted baggy jeans, $69


Madden Girl Tornado bootie

Madden Girl Tornado bootie
DSW

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

Madden Girl Tornado bootie, $70


Dr. Martens Leona 7-hook boots

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

Make a punk-rock-inspired statement with these platform boots.

Dr. Martens Leona 7-hook boots, $119 – $186


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.


Transcend – Claudine coated double button high waist ankle flare jeans

Paige Transcend - Claudine coated double button high waist ankle flare jeans
Nordstrom

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

Transcend – Claudine coated double button high waist ankle flare jeans, $149 (reduced from $249)


Mother The Hustler Frayed Ankle Jeans

Mother The Hustler Frayed Ankle Jeans
Nordstrom

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

Mother The Hustler Frayed Ankle Jeans, $248


Tan crocodile pointed-toe mid calf boots

Tan crocodile pointed-toe mid calf boots
Lulus

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

Tan crocodile pointed-toe mid calf boots, $58


My Generation tan snake high-heel mid-calf boots

My Generation tan snake high-heel mid-calf boots
Lulus

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

My Generation tan snake high-heel mid-calf boots, $48 


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.


Banana Republic high-rise light wash bootcut jean

Banana Republic high-rise light wash bootcut jean
Banana Republic

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. 

Banana Republic high-rise light wash bootcut jean, $35 (reduced from $70)


Levi’s 70’s high flare jean

Levi's 70's high flare jean
Shopbop

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

Levi’s 70’s high flare jean, $98


Veronica Beard wide-leg jean

Crosbie Veronica Beard wide-leg jean
Shopbop

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

Veronica Beard wide-leg jean, $298


Anne Klein Prescott bootie

Anne Klein Prescott bootie
DSW

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

Anne Klein Prescott bootie, $80


Journee Signature Carmela western bootie

Journee Signature Carmela Western bootie
DSW

Cowboy boots definitely put the boot in bootcut. These western booties will bring some cowboy flair with a much shorter ankle cut.

Journee Signature Carmela western bootie, $65


Mags tortoise patent ankle booties

Mags Tortoise Patent ankle booties
Lulus

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

Mags tortoise patent ankle booties, $58


Cambridge Select lug sole platform ankle bootie

Cambridge Select lug sole platform ankle bootie
Cambridge Select via Amazon

These chunky platforms have comfortable and thick block heels and will elevate any style of jean.

Cambridge Select lug sole platform ankle bootie, $35 and up 


Everlane Italian leather square toe Chelsea boot

Everlane Italian leather square toe Chelsea boot
Everlane

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

Everlane Italian leather square toe Chelsea boot, $195


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