How to Wear Boots with Dresses: 6 Ways

TOMS booties shown.

When it comes to the ultimate fashion necessity, boots reign supreme. Warm, comfortable, cute, and versatile, these shoes for women facilitate the wardrobe transition from fun in the sun to sweaters and pumpkins with ease.

Plus, boots tend to pair well with everything in your closet, from jeans and leggings to skirts and rompers. When it comes to how to wear booties with jeans and pants, you could probably do that in your sleep. But, what about dresses? 

We think dresses and boots go together like bread and butter. This powerhouse style duo can even keep you wearing your favorite summer dresses longer into fall with a little bit of creativity and a touch of layering. 

To learn more about how to wear boots with dresses, look no further. Below, you’ll find our most cherished boot styles to pair with dresses and the best ways to wear them for a knockout fit. 

#1 Cutout Wedge Bootie

A stacked wedge bootie gives you the effortless combination of height, support, and style that will complement any outfit—including dresses. Add a side cutout into the mix, and you have transitional footwear perfection. 

The Kallie Wedge Bootie in a light, neutral cream will help you ease your way out of summer and into fall. That’s because it looks equally fab with a light and breezy summer dress as it does with a cozy, chunky sweater. Bonus points for its ultra-comfortable OrthoLite® insoles that keep your feet happy while you’re showing off your favorite dress. 

Ways to Wear Your Kallie

Outfits with booties are practically as endless as those long summer days, and we’ve got a couple of pairings that’ll kick your morning off right and let you savor that first sip of coffee a bit longer:  

  • Summer transition – If ever there was a boot to pair with a flowing, bright, patterned sundress, this is the one. While the weather is still warm, slide on the booties and throw on your maxi dress for an easy, breezy look. As the breezes start to get cooler, add in a sheer set of tights and top it off with a tie-front sweater. When planning for a cross-season wardrobe, layering will be your loyal friend.
  • Business chic – The sleek and unique lines of the Kallie boot lend themselves well to a corporate, semi-casual look. Pair this beyond cute boot with a smart, slim-fitting sheath dress in a classic navy with white stripes, and cover up with a tailored navy blazer. You’ll look elegant from your first meeting to your last email.

Heels & wedges that bring style and impact toward a brighter future. Shop the collection. Cropped feet view of models wearing TOMS heels and wedges.

#2 Cheetah-Print Wedge Boot

A neutral animal print is the ideal way to bring some personality into your footwear. Upgrade that with the peekaboo cutout of the Lea Boot, and you’ve got yourself a head-turning combination. Its open detail at the foot arch and medium-height, stack leather wrap heel enhance and accentuate the cheetah pattern. 

When it comes to what to wear with leopard print shoes, there are so many ways to style animal prints like leopard and cheetah, allowing you to take your dress-centric outfit in a number of style directions from casual to cocktail party. 

Ways to Wear Your Lea

The sky’s the limit when you’re dressing with cheetah print, but we’re giving the following looks five stars:

  • Let the shoe be the star – Well, you’ll be the star—but your shoes will come in as a close second. A black, short-sleeve shift dress that’s tight and boxy will have you looking effortlessly cool. Accessorize with large metal hoop earrings, a bold red lip, and a patent leather clutch if you’re hitting the town.
  • Stay casual in denim – Try pairing the cheetah print of the Lea with a fitted denim jumper dress. Keep your shoulders bare for a casual warm-weather fit or slip a white long-sleeve top underneath when the colder winds come knocking. Complete the look with a tousled pony and hoop earrings.

TOMS heels and wedges shown. 

#3 Chelsea-Inspired Boot

If you need to be uptown, downtown, midtown, and everywhere in between, a Chelsea-style boot is the best way to get you there. Styled like a classic bootie, the Chelsea boot has an added elastic panel at the ankle that makes putting them on and off a breeze—plus, it allows for more breathability when walking.

Our Everly Boot takes that timeless Chelsea-inspired style and elevates it with a chunky block heel and an OrthoLite® insole for comfort that will truly take you everywhere. 

Ways to Wear Your Everly

If you’re used to wearing this workhorse boot style with jeans, consider styling your Chelsea boots with a dress in the following ways:

  • Modern boho – The chunky heel and soft suede of these brown ankle boots work effortlessly with the earthiness of a boho look. Give the seventies throwback a modern twist by wearing this boot with an Indian cotton midi dress in a bold modern print, and top it with a fringed vest and an oversized, wide-brim hat. 
  • Country cute – You may not be living in a little house on the prairie, but you can bring out your inner Laura Ingalls Wilder by wearing a prairie dress made in cottagecore heaven. Make sure it's midi length and has just the right amount of ruffle to show off your suede Everly boot. 

Prefer the classic look of the timeless Chelsea boot? Be sure to check out our newly-launched Charlie Boot featuring the perfect heel height for all-day comfort, and double goring for easy on and off.

#4 Grey Wedge Bootie

If you’ve ever had any reservations about looking fab in a dress and ankle booties, putting on a dark grey, wedged pair will instantly change your mind. 

With a rounded toe and stacked wedge heel, the Kayley Boot brings ankle booties to new heights. The best part of adding a touch of height to your wedge-heeled ankle boot is that it’ll give the illusion of elongated legs, which makes pairing this boot with any dress length a breeze. 

Ways to Wear Your Kayley

Before you slide into the oh-so-comfy Kayley boot, keep these stylish pairings in mind: 

  • Cozy monochrome – For a strong but subdued statement, opt for a fully monochrome look. Start with the grey suede Kayley boot, of course, and build from there by adding a chunky knit sweater dress in a slightly different shade. Cinch it with a grey or black belt for an outfit that’s just as cozy as it is flattering.
  • Coastal grandmother – Embrace the newest trending aesthetic by pairing your Kayley boot with a white linen midi dress with a button front and round hem. Couple it with a long, loose-knit cardigan, wide-brimmed hat, and oversized dark sunglasses. You’ll find yourself feeling the salty sea breeze while sipping lemonade on Martha’s Vineyard in no time. 

TOMS Kelsey wedges in grey, leopard, and black colorways shown.

#5 Black Leather Wedge Bootie

There’s no other wardrobe staple more necessary than a wear-everywhere black wedge ankle boot. The Kelsey Boot will be your go-to bootie all year round with its rounded toe, stacked heel wedge, and textured detail. 

Ways to Wear Your Kelsey

From mini to maxi, this ankle boot looks sharp with dresses of all lengths and shapes. Don’t believe us? Try these styles on for size:

  • Shirt dresses – The streamlined look of these black ankle boots call for a dress that can match its utilitarian sophistication. Enter: the shirt dress. Whether you prefer the 1950s cinched waist and full skirt or a more simple shift silhouette, a button front and Oxford collar command respect and look effortless all at the same time.
  • Twinning – Do you have a young sister, daughter, or niece in your life who loves to be your shadow? The Kelsey comes in a youth style as well, so you can both embrace the dress and boot ensemble together. 

#6 Flat Ankle Boot

We get it—heels aren’t exactly everyone’s cup of tea. Sometimes you need to feel closer to the earth with a flat-heeled boot that’s so comfortable you might even forget you’re wearing it. 

Ways to Wear Your Reese

Even if you’re someone who usually goes for a heel or wedge, adding a flat boot like the Reese Boot to your wardrobe rotation will give you a greater number of styling options when thinking of how to wear flat ankle boots with dresses. Here are a couple of options to get you started:

  • Earthy asymmetrical – Pair the taupe grey Reese with neutral leggings and a sheer high-low dress in olive green. Accessorize with a chocolate suede cross-body bag for a desert-inspired look with an asymmetrical twist.
  • Cozy mini – If comfort is number one on your list, channel the cozy power of hygge when you pair your Reese boot with fleece-lined tights and a chunky rib-knit turtleneck mini dress. Trust us—it’ll be the next best thing to a snuggle on the couch—and you’ll look effortlessly stylish all through the fall and winter.  

Find The Perfect Boot for Your Dresses with TOMS

By now, you’re probably fully convinced that dresses and boots go together like cookies and milk: they bring out the best qualities in each other. Whether you’re feeling sweetly sophisticated or daringly edgy, there’s a perfect bootie and dress combo to match your style and your mood.  

If you already have the perfect dress in your closet and are in search of the best footwear to enhance your look, consider leveling up your dress with one of the many styles of boots for women TOMS has available. Dark, patterned, and heeled or light, solid, and flat, your feet will thank you for dressing them in boots that combine trendy designs with cloud-level comfort. 

Dip your toes into the delectable duo of dresses and boots—you won’t regret it. 

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Reviewed By Andrew David Stewart

Andrew David Stewart is the Manager of Digital Marketing at TOMS and has been working in the digital marketing and social media world for 6 years. Andrew is a lover of nature and the outdoors, and is passionate about telling stories through digital media.