14 Dresses With Boots Outfits

(Image credit: Getty Images/Edward Berthelot)

published 23 April 20

A quality pair, or two, of boots are our year-round wardrobe staples. We have our shearling ankle boots with skinny jeans for winter, but for the warmer months, we turn to a classic white bootie—or perhaps a more colorful option—to wear with our flirty summer dresses. Some shoes, however, like the timeless combat boot, are season-less and work with any outfit. So, for spring/summer 2020 we encourage you to bring out all your favorite boots and add them to your sandal/sneaker rotation. If you need ideas on how to wear them, from patent leather to the platform to even waterproof styles, we have that covered too. (If you're obsessed with black ankle boots and need ideas for outfits around those specifically, we got those as well.) Ahead, we rounded up a few of our favorite street style (and celeb) ensembles featuring the tried-and-true dress with boot combination. Consider this your summer look to master.

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Aim High

Platform boots were all over the fall/winter 2020 runways. They give you that added height to any outfit, but still support and cushion the soles of your feet. Take inspo from Alyssa Coscarelli and style your chunky footwear with a romantic corset dress.

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Jeffrey Campbell Mexique Boot

These platform boots are the perfect affordable and easy-to-style introduction to the trend. The shoe is also giving us major Bratz doll vibes.

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Brock Collection Floral Moiré Bustier Dress

On our wishlist is to own something from Brock Collection, like this bustier minidress.

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Buckle Up

Large buckles always add an elegant touch to any look (just think back to the classic Manolo Blahniks). Try pairing a chic buckle boot with a sequin dress for your not-so-serious going-out look.

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Roger Vivier Viv Two-Tone Western Booties

These buckle boots give me 17th century vibes with a contemporary feel for 2020. They'll go with everything from dresses to jeans.

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Ganni Sequin Minidress

A sequin minidress fit for a night out with the girls. You can easily make this daytime appropriate with a pair of minimalist white kitten heel sandals.

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Go for the White Boot

In the winter, we wear our favorite black boots to death. In the summer, we have the white boot. This shoe looks best when paired with a brightly colored dress because the outfit truly screams summer. Plus, this effortless outfit requires little time to throw together.

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Dorateymur Stainless Ankle Boots

The most interesting part about this ankle boot is the heel. This will be your go-to footwear for the season.

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Staud Tangier Ruched Cutout Dress

Raise your hand if, when you don't know what to wear, you just throw on a maxi dress. This one with a cutout in the middle is our pick for easy dressing.

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Lace Me Up

Knee-high lace boots might take a while to slip on, but the end result is definitely worth it. To get street style star Reese Blutstein's look, rock your lace-up shoes with a knee-length dress and an oversize beige trench coat.

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Frye Veronica Combat Tall

Swap your classic ankle combat boots for this one with a higher shaft.

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Sea Olive Puff Pleated Sleeve Cotton Midi Dress

Complete your Reese Blutstein-inspired ensemble with a puff-sleeve dress.

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Play With Textures

Kendall Jenner's patent leather boots look fresh and unexpected when paired with a breezy silk minidress. Keep your outfit to only one color: our pick would obviously be black too.

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Prada Square Toe Knee-High Boot

These 3.25-inch heel boots will give you a boost in height to make your legs look miles long.

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Fleur Du Mal Sleeveless Minidress

A cowl neck LBD that will never go out of style.

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Add Some Edge

There's nothing like a pair of chunky black boots to add some edge to a floral minidress. Leather jacket and amazing genetics: optional.

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Dr. Martens Smooth Black Combat Boot

If you're shopping for your first pair of combat boots ever, you need some Dr. Martens in your life. If not, you still need some Dr. Martens.

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LoveShackFancy Belle Smocked Floral Mini Dress

A pair of combat boots will easily turn this sweet and feminine look into a cool-girl ensemble for summer.

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Waterproof Your Look

Water-resistant boots aren't only for fall/winter weather. For sudden rain storms in the spring and summer (how does the saying go...April showers bring May flowers?), be prepared with a sleek and dark-colored rain boot that will match your more summery frocks.

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Hunter Original Tall Black Rain Boots

For those unexpected rain showers in the summer, simply slip into these Hunter boots.

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Pretty Little Thing White Cotton Poplin High Neck Smock Dress

The boots will work well with this high-neck long-sleeve minidress.

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Sparkle and Shine

Silver boots are the fun, do-anything friend you wish you had. Pair them with a denim outfit like Olivia Culpo did for a night out with your girls.

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Simon Miller Glitter-Effect Boots

If you are looking to make a statement, try these glitter boots for next outing (hopefully it soon). You will get plenty of compliments.

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Ulla Johnson Wren Stretch Denim Dress

Make a bold style statement in this structured shoulder denim dress.

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Ride 'Em Cowgirl

Cowboy boots add that unexpected western vibe to a dress for summer, especially when everyone else is in sandals or sneakers.

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Toga Pulla Tall Buckled Boots

The upgraded cowboy boot you need in your closet. It's worth investing in a pair like this to wear all year long.

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Free People Whistler Button Down Dress

This shirtdress has a flowing silhouette if you prefer clothes that aren't as formfitting. You can wear it with cowboy boots or leave it unbuttoned and styled with denim shorts and a ribbed tank.

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Show Some (Selective) Skin

Bored of your classic LBD look? Wear your favorite black dress with a pair of super sexy thigh-high boots. Less (skin) is more this summer. Plus, your legs will stay warm if the temperature suddenly dips.

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Jeffrey Campbell Parisah Over the Knee Boot

Is it just us or do all celebs and models own a pair of these? Try an over-the-knee boot to make you feel like a star.

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Anemone Tie-Back Washed-Georgette Mini Dress by Anemone

The perfect LBD for the days when you just want to throw on anything and still look good.

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Go Nude

Follow Mrs. Bieber's lead for a boot outfit that makes your legs look miles long.

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Dear Frances Spirit Boot

You can never go wrong with a nude pair of boots. They will pair nicely with an endless amount of pieces.

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Zimmermann Super 8 Mini Silk Wrap Dress

This blue hue is the perfect color to introduce to your spring/summer wardrobe.

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Keep It Monochrome

An all-white look feels super sleek and refreshing for summer. Save this for your next business meeting to elevate your office attire.

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Jimmy Choo Mavis 100 Boots

These white knee-high boots will look great underneath a trench coat or maxi dress.

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BB DAKOTA I Spy Textured Twill Trench Coat

A classic trench coat that you can also rock as a dress for seasons to come.

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Keep It Short

Ankle boots are a perennial staple because they go with everything in your wardrobe. Case in point: this summery white mini dress on Margot Robbie.

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Alexander Wang Kori Ankle Booties

Simple and chic, these Alexander Wang boots with an edgy heel goes with everything.

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Diane von Furstenberg Martina Silk Chiffon Ruffle Mini Dress

Ruffles and polka dots, yes please. You will want to live in this minidress from summer into fall.

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Play With Prints

Snakeskin is everywhere regardless of the season, and there's no better way to wear it than with your go-to little black dress. Take a page out of Sofia Richie's playbook and go all in with a knee-high style.

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