Boot season is arguably the best season. And knowing how to style boots with your dresses opens up a whole new world of styling possibilities, which is why I'm here to break down all the ways you can wear them with mini dresses, midi dresses, maxi dresses, sweater dresses, denim dresses... you get the point.
For all the types of dresses that exist, there are equally as many types of boots: knee-high, thigh-high, ankle, lug-sole, combat, cowboy, square-toed, suede. Again, you get it. Because the countless combinations can be overwhelming, the easiest place to start is looking at what formulas street-style stars have been tapping.
No matter your aesthetic, I can guarantee you'll find an outfit below you'll want to replicate this season. From frilly lace dresses and suede boots to classic LBDs and cowboy boots, I've covered a wide styling spectrum and shopped out similar pieces so you can recreate the looks for yourself.
Bohemian Vibes
Bring on the romance with a lacy, tiered mini dress in a neutral hue. A long pendant necklace is a must for any sort of boho look and the burgundy boots add some color while still complementing the rest of the ensemble.
Amber Sceats Owen Necklace
Tularosa Lyla Mini Dress
Dolce Vita Auggie Boots Wine Leather
Tonal Gradients
You can never go wrong when you mix different shades of brown. The cowboy boots, the plaid dress, and the layered necklace all work so well together. When you throw on an eye catching tan jacket, the whole look is complete.
Steve Madden Dean Jacket
Isabel Marant Etoile Naerys Dress
Tecovas Annie Boots
A Great Statement Coat
Another classic is a little black dress with black boots. So simple and chic, right? But if you're looking to jazz things up a bit with some color, throw on a coat that's impossible to miss like this yellow one that coordinates with those fall leaves.
Miss Selfridge Faux Leather Trench
Misng Square Neck Bodycon
wetkiss Black Knee High Boots
Winter Whites
Not wearing white after Labor Day is one of those fashion "rules" that's basically no longer a rule. A cream long-sleeve maxi dress definitely brings the drama. Plus, this style looks stunning with suede boots and a woven bag to really lean into the fall vibes.
Princess Polly Snyder Open Back Long Sleeve
Sam Edelman Sylvia Knee High Boot
A Layered Mini
A mini dress with a low-cut neckline is made to layer. Wear a striped button-down underneath to add extra interest, and then add brown knee-high boots to balance things out just right.
Banana Republic Cotton Poplin Swing Mini Dress
Dolce Vita Virona H2O Boots Dk Brown Suede
Sweater Dress + High Socks
This outfit is proof that your socks don't have to hide behind your boots. Hike them up above your footwear to give them their own moment. These sheer navy ones complement the black boots and grey cable knit sweater dress to create the perfect cool-toned ensemble.
H&M Rib-Knit Dress
Steve Madden Lytton Boot
Leopard Print
Lug-sole combat boots are a nice contrast to the the glamorous vibe of a leopard-printed maxi and chainmail crossbody bag. Basically, it's the wrong shoe theory proving itself yet again.
WuDiaoer Metal Sequin Purse
Never Fully Dressed Satin Cowl Neck Maxi Dress
DREAM PAIRS Knee High Boots
Denim + Silver Details
Denim might seem like a casual material, but when you pair it with silver boots and statement drop earrings, it becomes instantly elevated. Add some sunnies, and everyone will be asking, "Who is that?"
Heaven Mayhem Wing Earring Silver
Cream + Snakeskin
These snakeskin-printed boots are practically made to be worn with a cream dress, so this is your sign to try it out yourself. A black sling bag with silver hardware completes the effortless vibe, and keeps all eyes on the shoes.
Madewell Crescent Sling Bag
Endless Rose Oversize Long Sleeve Rib Sweater Minidress
& Other Stories Kitten Heek Leather Knee Boots
Green on Green
This gives a whole new meaning to the phrase, "Going green." Wearing a midi dress and jacket in similar shades makes getting dressed super easy... without sacrificing style, obviously. Black boots and a black bag are classic accessories that complement your whole ensemble, and then you can double down in the jewelry department with gold earrings and a chain necklace.
Lost Pattern "Modular" Silk Skinny Scarf Green
Vagabond Shoemakers Blanca Leather Bootie
Mixing Brown and Black
To all the moms who told us growing up that you can't mix black and brown (just me?), I present this look. A lacy mini dress in a warm espresso shade provides a nice contrast to the jet-black leather jacket and calf-high boots.
Quince 100% Leather Cropped Zip-Front Jacket
NIA Bailey Dress
Coconuts by Matisse Autumn Engineer Boot
Suede Accessories
For an absolutely luxurious look, pile on the neutrals and textured fabrics. The texture of this neutral dress plays nicely with the suede bag and boots.
Zara Split Leather City Bag
H&M Rib-Knit Dress
Circus NY by Sam Edelman Yulia Pointy Toe Knee High Boot
Eclectic Grunge
50 percent grunge, 50 percent Western, 100 percent chic. A strapless midi dress might seem like it screams summer, but when you tie a plaid shirt around your waist and throw on some tan booties, the look transitions seamlessly into fall.
Uniqlo Flannel Boxy Cropped Shirt
Enza Costa Cotton Resort Strapless Dress
Belted Dress + Slouchy Boots
I'm all about belts at the moment. Whether it's built into the dress or added on top, they completely transform a silhouette. This edgy mini looks great with semi-slouchy boots, and you can always add a jacket if you're taking the look from day into night.
Petal & Pup Hailey Denim Mini Dress
Marc Fisher Paityn Boots
Bold Prints
If your dress hits just above the knee, knee-high boots are actually a fab and unexpected choice. This buffalo plaid definitely turns heads, so if you're opting for a printed style, a solid-colored boot keeps all the emphasis on the dress.
JW Pei Hana Mini Faux Suede Tote Bag
Hill House Home The Rennie Dress
Schutz Raffaela Up Mid Suede Boot
I'm Cosmopolitan's Associate Fashion Editor and write about any and all trends, major celeb fashion moments, and why wide-leg jeans are basically the best. I originally moved to New York City to audition for RENT, only to find out that the play closed 10 years ago.
