10 Fashionable Ways to Wear Boots With Dresses (2024)

Style
Shoes

A foolproof outfit formula.

Gina Marinelli

Gina is a freelance writer and editor covering fashion, beauty, and entertainment. She's written for The Zoe Report, Glamour, Coveteur, MTV News, and Insider.

Byrdie's Editorial Guidelines

Updated on 09/11/23 03:02PM

10 Fashionable Ways to Wear Boots With Dresses (2)

As cliché as the phrase might be, we want our wardrobes to work smarter, not harder. That means shopping thoughtfully for pieces that complement each other and offer tons of variety as far as styling is concerned. For this reason, the dress-and-boots combination will forever be a favorite for anyone whose agenda is having pulled-together looks that require minimal energy.

The pairing of dresses and boots is about as easy as wearing jeans and a T-shirt but feels slightly more elevated. "One trick I love is making sure the top of the boot is covered by the dress," says Elisabeth Kassab, a professional stylist and personal shopper, "For example, if I was wearing a midi or maxi length dress, I would pair it with a tall boot tucked underneath.This is chicer and more put together than having the top part stick out. "

Some quick and simple combinations include Western boots with sweet, smocked minis or lug soles with a '90s-reminiscent slip dress, but the options extend well beyond these.

Ahead, we’re breaking down 10 foolproof, stylish recommended adaptable examples of how to wear boots with dresses.

Meet the Expert

Elisabeth Kassab is a personal shopper and professional stylist based out of Michigan and New York.
Jeni Paolella is a celebrity personal stylist and lifestyle reporter based out of Connecticut.

01of 10

Lug-Sole Boots and Slip Dress

10 Fashionable Ways to Wear Boots With Dresses (3)

Though definitely a nod to the '90s, the combination of a silk slip dress and heavier boots has staying power. Kassab loves this combo for its masculine feminine mix."I love the grunge of the shoe paired with the delicateness of a slip," she says.

Wear it in warmer weather or layer in a long-sleeve tee or turtleneck, and take this outfit well into chillier temperatures, too.

02of 10

Western Boots and Nap Dress

10 Fashionable Ways to Wear Boots With Dresses (4)

Paolella finds this pairing both sexy and approachable. A pair of Western boots like the Ganni Embroidered Leather Knee Boots ($825) ground an airy nap dress like the Hillhouse Matilda Dress ($198).

"This is a timeless pairing and tell the story of a woman who is approachable and fun, carefree and sexy at the same time," says Paolella.

03of 10

Over-The-Knee Boots and Mini Dress

10 Fashionable Ways to Wear Boots With Dresses (5)

Consider this your excuse to bust out your micro-mini dress. Over the knee boots like the Schutz Kaolin Stretch Patent Boot ($198) usually signal short hemlines, but take a hint from the photo above and choose a baggy silhouette. A flash of upper thigh adds some sex appeal to the look and the loose fitting fabric keeps the look both casual and comfortable.

Sleek Neutrals and Bold Prints

10 Fashionable Ways to Wear Boots With Dresses (6)

Who doesn’t love a print comprised of lush florals? Keep the iconic spring dress trend feeling modern with a classic tan bootie that has a streamlined silhouette. This look transitions seamlessly into summer, too.

05of 10

Printed Booties and Shirtdress

10 Fashionable Ways to Wear Boots With Dresses (7)

A crisp shirt dress is timeless and great for most professional settings, should you need that. We suggest pairing it with a chunky, printed bootie that’ll add a bit of pizazz to the timeless style.

06of 10

Lace-up Boots and Voluminous Midi Dress

10 Fashionable Ways to Wear Boots With Dresses (8)

Apply wrong shoe theory to your outfit formula. Instead of wearing a feminine sandal or sleek heel, pair your favorite flowy dress like the By Anthropologie Short Sleeve V-neck Button Front Midi Dress ($170) with a chunky, lace-up boot like Madewell Rayna Lace Up Boot ($160).

07of 10

Suede Knee High Boots and Knit Dress

10 Fashionable Ways to Wear Boots With Dresses (9)

If you have a penchant for knit dresses, we get it the DISSH Sienna Olive Knit Midi Dress ($150) has been on wishlist for ages, a suede knee high boot, like the Staud Wally Suede Knee High Boots ($495), is the perfect cozy fall companion.

08of 10

Flat Boots and Mini Dress

10 Fashionable Ways to Wear Boots With Dresses (10)

Meet your new every day, any day, two-piece uniform: a mini dress and flat boots. Don’t be surprised if you end up reaching for this low maintenance look more often than for your favorite jeans.

09of 10

Leather Boots and Oversized Blazer

10 Fashionable Ways to Wear Boots With Dresses (11)

The suiting trend is not going anywhere. If you need a look to transition from summer to fall, pair an oversized blazer dress like the HM Boulce Weave Jacket Dress ($90) with a bold, leather boot.

10of 10

Rain Boots and Sweater Dress

10 Fashionable Ways to Wear Boots With Dresses (12)

Regardless of what trends may say, rain boots will never go out of style especially during fall and spring months. This year, bust our your favorite rubber boots and wear with a lightweight sweater dress for a practical yet sophisticated look. We love the Hunter Short Waterproof Rainboot ($150) and the Reformation Evan Cashmere Sweater Dress ($189).

42 Makeup Ideas to Wear With a Black Dress