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13 Cute Dresses With Boots Outfit Ideas

Done right, this look is effortlessly chic.

Street Style - Berlin - May 31, 2019
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If you're like me, you know that a quality pair of boots are a year-round wardrobe essential. While you might believe they're only meant to be worn over your old faithful pair of jeans in the winter months, consider styling your boots with a flirty dress this season. Not only does the look super thrown-together (in a cool way, of course), but you get more wear out of the items in your closet. Check out our favorite ways to wear the unexpected pairing, and you'll forget why you packed your boots away in the first place.

Celebrity Sightings In Paris -  September 25, 2017
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Add Some Edge

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

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Smooth Black Combat Boot
Dr. Martens amazon.com
$140.00
$106.58 (24% off)
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Mini Silk Slip Dress
Nudwear shopbop.com
$150.00
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Street Style: June 16 - Milan Men's Fashion Week Spring/Summer 2020
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Keep it Cowgirl

Cowboy boots are one of this summer's most unexpected trends. Choosing a stylish color lets your fashion girl shine through.

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Tall Buckled Boots
Toga Pulla shopbop.com
$690.00
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Pink Floret Button Down Cover Up
Maaji shopbop.com
$43.00
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Celebrity Sightings in New York City - September 6, 2016
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Go See Through

For the days when you want to make a real statement, consider wearing a shoe that shoes a bit more skin. Thankfully, you don't have to go full Kim K to achieve the same look.

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Blaire 100 Boots
Malone Souliers shopbop.com
$318.00
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Oversized Mini Dress
Asos DESIGN us.asos.com
$32.00
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Celebrity Sightings in Los Angeles - June 29, 2019
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Play With Textures

Jenner's patent leather boots look fresh and unexpected when paired with a breezy silk mini dress. Keep the look all one color to for bonus cool points.

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Square Toe Knee High Boot
PRADA nordstrom.com
$1,200.00
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Belted Satin Playsuit
Fleur du Mal net-a-porter.com
$297.00
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Street Style - LFW September 2018
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Make any Outfit Weatherproof

We've all seen the photo of Kate Moss trekking through the mud at the Glastonbury Festival in her rain boots and slip dress, looking incredible. If it ain't broke, don't fix it.

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Original Tall Black Rain Boots
Hunter amazon.com
$99.91
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Vienne Dress
Ulla Johnson shopbop.com
$330.00
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Celebrity Sightings in New York City - April 22, 2019
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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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Knee High Slouch Boots
Olivia and James amazon.com
$299.99
$199.99 (33% off)
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Oversized Denim Shirt Dress
Missguided Tall us.asos.com
$45.00
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RBC Hosted "Her Smell" Cocktail Party At RBC House Toronto Film Festival 2018
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Show Some (Selective) Skin

Bored of your classic LBD look? Wear your favorite 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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Lancaster Over-The-Knee Suede Boots
Aquazzura saksfifthavenue.com
$870.00
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Vesper Tall Square Neck Mini Dress
Vesper Tall us.asos.com
$79.00
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Celebrity Sightings In New York City - May 09, 2019
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Pop of Color

Has following a Spice Girl's fashion advice ever been a bad idea? Victoria Beckham (AKA Posh Spice) lives up to her title in a pair of cherry red peep-toe heels with an otherwise simple outfit.

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Porto Boot
ALEXANDRE BIRMAN nordstrom.com
$950.00
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Striped Cutout Handkerchief Dress
BCBGMAXAZRIA bloomingdales.com
$278.00
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Street Style - Paris Fashion Week Womenswear Fall/Winter 2019/2020 : Day One
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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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Beha Almond Toe Booties
rag & bone bloomingdales.com
$525.00
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Olivia Button-Down Midi Dress
leRumi bloomingdales.com
$148.00
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Street Style - New York City - July 2017
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Cut it Out

Cut out booties: They're just like sandals, but better.

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Black Ceinture Leather Ankle Boots
Balenciaga farfetch.com
$1,390.00
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Leopard Silk Slip Dress
Fleur du Mal saksfifthavenue.com
$279.00
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