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. Some quick and simple combinations include Westen 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, adaptable examples of how to wear boots with dresses.
Lug-Sole Boots and Slip Dress
Though definitely a nod to the '90s, the combination of a silk slip dress and heavier boots has staying power. Wear it in warmer weather or layer in a long-sleeve tee or turtleneck, and take this outfit well into chillier temperatures, too.
Western Boots and Nap Dress
As much as we love a frock intended for sleeping, the look feels surprising right at home with a Western boot. We especially like a taller style that contrasts a short hem of the smock-detail mini dress.
Over-The-Knee Boots and Swing Dress
Even if you’re not the twirling type, a swing dress will make you want to give it a go with its playful, bouncy hemline. The best way to complement this silhouette is with a flat, tall, and minimalist boot—anything with a spindly heel or delicate is a bit too obvious for our taste.
Sleek Neutrals and Pastoral Prints
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.
Printed Booties and Shirtdress
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.
Lace-up Boots and Tiered Midi
Avoid looking like you're wearing a uniform with a single color, from dress to boot. Keep it elegant and go for dresses, tights, and boots in the same color family—for example, layers of darks and lights in the same color family.
Cutout Boots and Knit Dress
If your ideal dress hugs your frame, opt for a modern knit design such as this cardigan-style one. Complete the ensemble with the ultimate transitional-season boot that has cutout details along the sides.
Flat Boots and Mini Dress
Meet your new every day, any day, two-piece uniform: a button-up chambray mini dress with sleek, black ankle booties with the most subtle square-toe stitching detail. Don’t be surprised if you end up reaching for this denim look more often than for your favorite jeans.
Two-Tone Boots and White Dress
You probably already own one part of this dress-and-boots look. To achieve it, pick your favorite lightweight white dress and give it a unique spin with vintage-inspired colorblock boots.