What Boots to Wear with Dresses?

You have the perfect outfit planned: a dress for the occasion, with a suitable hairstyle to complement it. The next step is choosing appropriate footwear that will ensure you’re comfortable and fashionable – but how do you know what works best?

Move over, pumps – boots are on the rise! Even with more formal dresses, there are boots that suit the look while expressing your personality. Keep reading to pick up some fashion tips that will help you decide what boots to wear with dresses, for any occasion.

what boots to wear with dresses

Types of Boots

Before we choose what boots work best with which dresses, let’s go over the different types to understand the pros and cons of each.

Ankle boots

These are the most versatile for pairing with dresses, especially in colder weather. Sometimes called booties, they wrap around the foot without traveling up too high on the leg, and come in every configuration imaginable. Slingback, peep-toe, lace-up, zip-up, or caged, the shape of these are endless – as is their style potential.

Biker boots

You don’t have to ride a motorcycle to appreciate the edgy effect of a biker boot. Strut your stuff in heads-to-toe leather, or don a more feminine dress with these no-nonsense boots for an eclectic style.

Combat boots

Military-inspired fashion was big in the 90s and is coming back again – and we couldn’t be happier. Big and bold, these always make a statement. The combat-boot look is a more casual one, though, making these the wrong choice for a more formal event.

Cutout boots

The open detail of this style practically begs for a pair of cute tights. For the late-autumn days when you aren’t yet ready to commit to socked feet, these are a great transitional choice. Wear with a long, cardigan-style dress to complete your seasonal look.

Equestrian boots

With a dress that is more feminine, like a flowery pattern or light material, equestrian boots can provide balance with a businesslike tone. Go minimalist with a basic shape, or find a pair with a buckle for some flair.

The silhouette of this style is typically long and sleek, so you can match it with an equally polished, form-fitting dress, or offset it with looser material.

Knee-high boots

With shorter dresses comes the ability to go higher in the boot. Show some serious leg game with boots that rise up higher, and accent with the help of a dress hem that is appropriate (more on this later).

Beware the calf issue! As a former soccer player, I can attest to the difficulty of finding tall boots that fit both the feet and the legs. Sometimes, women with defined musculature in the lower leg have trouble zipping up the boot to its full height. To avoid this problem, shop for boots that are roomier in the calf region – or that lace up instead of zip.

Open-toed boots

Best in summer and early autumn, you can do open-toed boots with just about any short dress. Trade up your flip-flops for boots for an elevated cocktail party look. Don’t forget the nail polish!

Platform boots

You can wear these for a punk-rock vibe, or to offset the femininity of a floral ensemble. The chunky shape adds bulk, so make sure to pair with a sleeker dress so you don’t appear overburdened with texture and material.

Protective boots

Who says dressing for inclement weather has to be blah? Pick up a pair of galoshes with an eye-catching design, or fur-lined snowboots that will add some flair to the blizzard raging outside, to stay warm and dry without sacrificing your style.

Sock boots

When feet embraced this trend a few years ago, we weren’t sure how long it would stick around. Turns out the answer is, quite a while! The form-fitting line of these boots helps your stride feel balanced and secure, and the sleekness of the shape allows for just about any long dress to sweep alongside their brim.

Suede boots

For a smooth transition from office to happy hour, suede boots are versatile and classy. Wear them with a pencil skirt to feel oh-so-grownup. Note that this material can be fussy – waterproofing spray will help preserve the suede in wet outdoor conditions.

Thigh-high boots

Drawing the eye to the length of your leg, these boots are flattering with no shortage of sex appeal. Over-the-knee height wants a midi dress to go with it, so you can show off your pins. These work great for shorter girls who want to extend their vertical lines. Show Pretty Woman some competition and strut your silhouette!

Wedge boots

These thicker-bottomed types are perfect for when you want the height and class of a heeled boot, but don’t trust yourself not to trip. Wedge boots are also extremely versatile, going casual or formal depending on what kind of dress you wear them with.

Western boots

There’s perhaps no more iconic regional style than the quintessential cowgirl look. Pull on a pair of basic Westerns for wear under almost any casual dress, or go for a more Dolly Parton-esque glam with boots that have rhinestone or pearl accents.

If you really want to drive the cowgirl theme home, add a wide-brimmed hat, jacket with fringe, or Southwestern-inspired jewelry like turquoise gemstones. There’s really no wrong way to do Western boots with a dress!

What Boots to Wear with Dresses – Choose your Style

All about the hemline

Ultimately, the best way to pair boots with dresses is by keeping an eye on the dress hem. There are a few tricks that can help:

  • Shorter dresses allow for taller boots. Extend your leg with a thigh-high boot and minidress combo.
  • Longer, flowy dresses need short boots. Try an ankle boot style to look cute without carrying too much material on your frame.
  • Formal dresses need sleek boots. You don’t have to forego a pair of boots just because you’re dressing up – but an equestrian, wedge, or classy ankle bootie will look better than, say, a platform boot, which takes away from the elegance of your dress.

Knee-high or thigh-high boots under a long dress is just silly, because no one will see them. On the other end of the spectrum, short boots and a short dress may bare too much leg than what you’re willing to show. In the end, it’s up to your taste and comfort.

To heel or not to heel

Boots – just like pumps – offer any size and shape heel you can imagine. Stiletto boots lend a touch of glam, while chunky wide heels (like on combat boots) provide support without rendering you unstable.

To dress up your outfit, try a boot with a sleek, medium height heel. You’ll look classy without the feeling of teetering over like you’d get in traditional heels.

Of course, if you’re in for a long day that involves a lot of walking, a flat boot is probably the way to go. Something like an equestrian style with added decoration will allow you a touch of pizzazz along with the practicality. 

Sometimes, that cute pair of boots you found on sale is at a discount because they’re uncomfortable. Make sure to try them on and walk around for a minute or two, to really feel how they support your feet. If they’re difficult to tolerate in the store, you won’t like them any better once you’ve purchased them.

It could be that it’s not the height of the heel, but the substance. A leather boot with a wooden sole adds earthiness, giving your dress a down-to-earth vibe. Pair these with a knit dress and tights for a classic autumn look. Or, try flowered boots with cork-bottomed accents for a summer cocktail party.

Prepare for Weather

The perfect boot-and-dress combo can be quickly thwarted with rain, mud, or snow. Make sure you check the weather forecast to protect your style as well as the lifespan of your cute boots. 

Depending on the elements, your style of boots may vary. Cutout boots aren’t going to be conducive to winter weather, as your feet will freeze. On the other hand, thigh-highs may not be the best option to stay cool in summer. Don’t forget socks to keep your feet dry and extend the wear of your boots!

Covering your knees is a fashion statement in itself. Do you want thick tights for warmth? Choose a geometric pattern for visual interest, and wear under chic black boots. Are you more of a leggings girl? A shade complementary to your boots can help you style in colorblock – or, go monochrome by matching them to your boots.

Make a Statement

Now that the important logistics are covered, it’s time to have fun with your outfit. This is where you can feel the fashion inspiration and let your creativity shine.


Who says your everyday style has to look everyday? Go to the office in a head-to-toe Western, military-inspired, or boho getup and enjoy the compliments you get on your polished look.


Sometimes a simple pop of color makes your whole outfit. If you make your boots the focus, it draws attention to your style without overpowering your look.

Not yet ready to commit to a loud color all over? Try it with your boots first. If you want to be fun without compromising your neutrals on top, a little black dress welcomes any splash of color on your feet. We recommend red or royal blue ankle booties, to start! 

You might also go monochromatic by coordinating your dress with boots that are the same or a similar shade. Try a pea green knit dress with hunter green knee-high boots, or an all-white ensemble for some brightness in spring.

For functionality, neutrals like brown or black will allow you to wear what you need for protection without taking away from your style. If you’re headed to a winter party in a snowstorm, for example, black snowboots will protect your feet while letting your dress steal the limelight.

Brown boots pair wonderfully with a denim ensemble, letting you be cute but low-key. They also work for earthy energy, such as supporting a boho maxi dress.

Still not sure what you’re into? Browse photo collections online to see what catches your eye.

A Timeless Pairing

Like cookies and milk, dresses and heels just seem to work together. But who said a pair of heels had to be pumps? Modernize your look year-round with boots that are chic and comfortable.

Adding boots to your wardrobe will dress down the elegance of some dresses, and elevate the casualness of others. No matter where you’re headed, they’re an easy option for effortless style.