10 Chic Ways to Pair Boots With Dresses

A foolproof outfit formula.

Woman wearing red dress and black boots

Getty Images / Westend61

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.

01 of 10

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.

Recycled Rubber City Boot
Ganni Recycled Rubber City Boot $245.00
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Vee Midi Slip Dress
Abacaxi X Svnr Vee Midi Slip Dress $425.00
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02 of 10

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.

 X Toe Elastic Wide Calf Western Boot
Ariat Heritage X Toe Elastic Wide Calf Western Boot $200.00
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The Athena Nap Dress
Hill House Home The Athena Nap Dress $100.00
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03 of 10

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.

Leather Knee-High Boots
Khaite Derby Leather Knee-High Boots $1,460.00
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Second Date Dress
Wray Second Date Dress $246.00
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04 of 10

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.

Pack Boots
Simon Miller Pack Boots $590.00
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Printed Relaxed Midi Wrap Dress
& Other Stories Printed Relaxed Midi Wrap Dress $149.00
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05 of 10

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.

Python-Effect Leather Boots
Paris Texas Python-Effect Leather Boots $645.00
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Relaxed Shirtdress With Belt
Eloquii Relaxed Shirtdress With Belt $120.00
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06 of 10

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. 

Gamin Lace-Up Boots
Jeffrey Campbell Gamin Lace-Up Boots $170.00
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Gingham Seersucker Ruffle-Sleeve Tiered Midi Dress
Madewell Gingham Seersucker Ruffle-Sleeve Tiered Midi Dress $148.00
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07 of 10

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.

Darcy Leather Buckled Booties
Allsaints Darcy Leather Buckled Booties $298.00
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Button-Up Long Sleeve Knit Midi Dress
Fourteenth Place Button-Up Long Sleeve Knit Midi Dress $59.00
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08 of 10

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.

Square-Toe Leather Ankle Boots
Neous Menea Square-Toe Leather Ankle Boots $640.00
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Chambray Buttoned Denim Mini Dress
Whistles Chambray Buttoned Denim Mini Dress $140.00
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09 of 10

Buckle Boots and Handkerchief Hem

We prefer to enjoy a pretty, handkerchief hemline with a tougher, buckle-detail moto boot. They make for the most unlikely yet perfect pair.

Buckle Ankle Boots
Mango Buckle Ankle Boots $60.00
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Sing Dress
Studio 189 Sing Dress $525.00
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10 of 10

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.

Twice As Nice Ankle Boots
Alohas Twice As Nice Ankle Boots $227.00
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Embroidered Cotton Dress
Violeta by Mango Embroidered Cotton Dress $130.00
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