Labor Day weekend has come and gone, which means fall is officially here. Whether that means returning to school, 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
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 dark wash
Or let this cool and casual simple straight-leg style replace your favorite skinny jeans.
Vagabond Shoemakers MYA stretch bootie
These sock boots pair perfectly with straight-leg jeans.
Everlane Glove boot
Or try this textured sock-like style of shoe for a more unexpected look.
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
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.
Spanx ankle skinny jeans
These skinny jeans from Spanx prioritize a sleek silhouette with a pull-on design and stretch denim that’s made for comfortable motion.
Vince Camuto Alimber knee-high boot
This boot, with its subtle crocodile-print pattern, brings a fresh take to the classic fall knee-highs.
So Much Yes black suede over-the-knee boots
Have an Ariana Grande Sweetener-era moment this fall with these over-the-knee suede boots that’ll go well with skinny jeans.
Baggy jeans warrant an extra chunky boot to complete a 90’s grunge-inspired look.
90’s Cheeky jeans
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.
BDG high-waisted baggy jeans
These baggy jeans can easily be your go-to for a comfortable and casual denim look.
Madden Girl Tornado bootie
These chunky ankle boots are timelessly trendy and made to be worn with your best pair of baggy jeans.
Dr. Martens Leona 7-hook boots
Make a punk-rock-inspired statement with these platform boots.
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
These ultra-soft cropped flare jeans are cut with denim that has a leather-like coating and subtle shine.
Mother The Hustler Frayed Ankle Jeans
These frayed ankle jeans with a ragged hem and subtle flair add a bit of edge to a classic denim look.
Tan crocodile pointed-toe mid calf boots
These vegan leather crocodile embossed boots will fill the notorious ankle gap caused by cropped flare jeans with some wild style.
My Generation tan snake high-heel mid-calf boots
Or try these sleek and bold snake print boots for a fierce fashion choice.
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
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.
Levi’s 70’s high flare jean
These flair jeans are unabashedly groovy and a statement piece for your wardrobe.
Veronica Beard wide-leg jean
These wide leg jeans have just a touch of flair to them for an immaculately subtle retro fashion feel.
Anne Klein Prescott bootie
Balance out that bell bottom with a boldly patterned choice in bootie, like these spotted leather ones from Anne Klein.
Journee Signature Carmela western bootie
Cowboy boots definitely put the boot in bootcut. These western booties will bring some cowboy flair with a much shorter ankle cut.
Mags tortoise patent ankle booties
These chic patent tortoise patterned booties have a rounded toe and block heels and will look fabulous peeking out from underneath your flair jeans.
Cambridge Select lug sole platform ankle bootie
These chunky platforms have comfortable and thick block heels and will elevate any style of jean.
Everlane Italian leather square toe Chelsea boot
These Chelsea boots are endlessly chic and utterly timeless, you can keep them as a staple in your fall wardrobe for years to come.