Labor Day weekend has passed, which means fall has officially arrived. That it means going back to school,or just to prepare for the arrival of sweater time, a solid fall wardrobe can help ease the transition to this new season. And there’s no better place to start than the fall essentials: a great pair of reliable boots and jeans.
From chunky ankle boots to suede thigh-high boots, and cropped flared jeans to baggy mom jeans, the ease of having interchangeable and stylish basics for the season should never be underestimated. Looking to make those summer skinny jeans last through fall? Try a unique take on the classic knee high riding boot. Thinking of testing the waters on a wide-legged figure? For this foray into fashion, a bold mid-calf boot will come in handy.
When in doubt, Chelsea boots pair well with just about anything and have a timeless style.
With that perfect pair of boots and jeans in your fashion arsenal, this season should be filled with style success. Here are 24 pairs of boots and jeans that go well together.
Straight leg jeans
Straight leg jeans can be a real puzzle when it comes to choosing a matching shoe style, but sock-style ankle boots are a simple and stylish solution. The fitted ankle boots slip easily under the hem of straight jeans.
Ultra High Rise ’90s Straight Jeans in Light Wash
Tik Tok seems to love these slightly faded straight leg jeans, grab one for fall.
Ultra High Rise ’90s Straight Jeans in Ripped Light Wash, $ 30 (was $ 99)
Ultra High Rise 90s Straight Jeans in Dark Wash
Or let this simple, relaxed straight-leg style replace your favorite skinny jeans.
Ultra High Rise 90s Straight Jeans in Dark Wash, $ 99
Vagabond Shoemakers MYA Stretch Boot
These sock boots go perfectly with straight jeans.
Vagabond Shoemakers MYA Stretch Bootie, $ 160
Everlane Glove Boot
Or try this sock-shaped textured shoe style for a more unexpected look.
Everlane Glove Boot, $ 120
Skinny jeans are the perfect opportunity to pull the boots out to the knee for maximum comfort and maximum style.
American Good Legs 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 space-proof waistband and are made from ultra-stretch denim for added comfort.
Good American Good Legs skinny jeans, $ 99
Spanx ankle skinny jeans
These skinny jeans from Spanx favor a sleek silhouette with a pull-on design and stretch denim designed for comfortable movement.
Spanx ankle skinny jeans, $ 128
Vince Camuto Alimber Tall Boots
This boot, with its subtle crocodile print pattern, brings a touch of freshness to classic fall knee socks.
Vince Camuto Alimber Knee Boot, $ 229
So Much Yes black suede over-the-knee boots
Experience a moment from the Ariana Grande Sweetener era this fall with these suede over the knee boots that will look great with skinny jeans.
So Much Yes black suede over-the-knee boots, $ 58
Baggy jeans justify a thicker boot to complete a ’90s grunge-inspired look.
Naughty 90s jeans
These high waisted straight leg jeans are made from premium non-stretch Japanese denim and have a ’90s-inspired look without being too baggy.
Naughty ’90s jeans, $ 88
BDG High-Rise Loose Jeans
These loose jeans can easily be your go-to for a comfortable and relaxed denim look.
BDG high-rise baggy jeans, $ 69
Madden Girl Tornado Boot
These chunky ankle boots are in timeless fashion and designed to be worn with your best pair of baggy jeans.
Madden Girl Tornado Boot, $ 70
Dr. Martens Leona 7 Hook Boots
Make a punk-rock inspired statement with these platform boots.
Dr. Martens Leona 7-Hook Boots, $ 119 – $ 186
Cropped flared ankle jeans
Cropped ankle flare jeans, while adorable, leave some ankle room in the open. This is where mid-calf ankle boots come in – fill that bare ankle space with a bold pattern that makes an elegant statement.
Transcend – Claudine double button coated high waist flared ankle jeans
These super-soft cropped flare jeans are cut from denim with a leather-like coating and subtle sheen.
Transcend Claudine Coated Double Button High Rise Flare Jeans, $ 149 (was $ 249)
Mother The Hustler Frayed Ankle Jeans
These frayed ankle jeans with a ragged hem and a subtle touch add a touch of originality to a classic denim look.
Mother The Hustler Frayed Ankle Jeans, $ 248
Pointed-toe mid-calf ankle boots in tan crocodile
These crocodile-embossed vegan leather boots will close the notorious ankle gap caused by cropped flare jeans with wild style.
Pointed-toe mid-calf boots in beige crocodile, $ 58
My Generation Tawny Snake High Heel Mid-Calf Boots
Or try these stylish and daring snake print boots for a fierce fashion choice.
My Generation Beige Snake High Heel Mid-Calf Boots, $ 48
Jeans with a little more flare in the leg open up a world of boot possibilities. A cowboy-inspired boot gives a nice nod to bootcut style, while a uniquely patterned ankle boot that pops out under a wide leg is sure to be a fierce fashion hit, and you really can never go wrong with it. a Chelsea boot.
Banana Republic Light Wash High Rise Bootcut Jeans
These bootcut jeans are perfect for anyone who isn’t ready to strut the street in bell bottoms, but still wants a vintage touch.
Banana Republic High Rise Light Wash Bootcut Jeans, $ 35 (was $ 70)
Levi’s 70’s flared jeans
These Flair jeans are decidedly groovy and a centerpiece of your wardrobe.
Levi’s 70s high flare jeans, $ 98
Wide jeans veronica beard
These wide leg jeans have just a touch of flair for an impeccably subtle retro fashion feel.
Wide Leg Veronica Beard Jeans, $ 298
Anne Klein Prescott Boot
Balance this bell bottom with a choice of boldly patterned ankle boots, like these speckled leather styles from Anne Klein.
Anne Klein Prescott ankle boot, $ 80
Western ankle boot Journee Signature Carmela
Cowboy boots definitely put the boot in the bootcut. These western ankle boots will bring a cowboy touch with a much shorter ankle cut.
Journee Signature Carmela Western Boot, $ 65
Mags tortoiseshell patent ankle boots
These chic patent turtle pattern ankle boots have a rounded toe and block heels and will look fabulous looking under your Flair jeans.
Mags patent tortoise ankle boots, $ 58
Cambridge Select platform lug sole ankle boots
These chunky platforms have comfortable, chunky block heels and will enhance any style of jeans.
Cambridge Select lug sole platform ankle boots, $ 35 and up
Everlane Square-Toe Chelsea Boot in Italian Leather
These Chelsea boots are endlessly chic and totally timeless, you can keep them as a staple in your fall wardrobe for years to come.
Everlane square-toe Chelsea boot in Italian leather, $ 195
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