Which Shoes to Pair With Dresses

So, you've found the perfect dress, and you're ready for a night out on the town. The only problem? You don't have any matching shoes. And when you try to shop for the right pair, there are hundreds of styles, colors, heights, embellishments and more to choose from.

What's a girl to do? If doubt is filling your mind, don't worry — you're not the only one. When it comes to the rules of shoes, we're all learning as we go along.

The truth is, there is no right or wrong answer. While you can follow the guidelines below to match up your dress with the perfect pair of shoes, keep in mind, they're just that — guidelines. Those daring enough to go against the status quo have created some of the most enduring fashion trends.

Luckily, whether you're a seasoned fashionista or a couture novice, there's some fundamental advice you can follow to make it easier to pair shoes with any dress.

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What Shoes to Wear With Dresses

Be sure to have your dress picked out before you go shopping for shoes. Like shoes, dresses come in a wide range of styles and colors. The shoe you look for will depend entirely on the type of dress you've selected.

The most common dress styles include:

  • Sheath
  • A-line
  • Evening gown
  • Maxi
  • Fit-and-flare
  • Wrap

Once you have the right dress, you can start your search for the perfect pair of shoes.


The basic design of pumps, also called court shoes, is an enclosed shoe with a cutout that exposes the top of the foot, starting near the toe. Classic pumps usually lack any decoration, like laces, buckles or straps.

Historians believe these shoes originated as far back as the 1400s, with shoes that raised women as much as 18 inches to give them height over rivals and appear more attractive to suitors. Men wore high-heeled shoes too, especially powerful men like King Louis XIV. Pumps signified a person was wealthy, a part of the aristocracy.

Around the 1600s, men ditched the heel for a more practical design, and pumps assumed their traditional role as a women's fashion trend.

What's great about pumps is their versatility — you can wear them with just about everything. If you have a fit-and-flare dress, pair it with some black tights and a matching pair of pumps. If you're going for a relaxed look, like a sundress or wrap dress, a set of heels can amp up the elegance. Or, a sheath dress paired with stockings and a set of metallic pumps can make you the star of your next office party.

Pro tip: To avoid the foot pain associated with heels, get your feet measured by a professional. One master shoe fitter in New York City says 95 percent of her customers don't know their correct shoe sizes. Finding the right fit will feel better and offer the proper support for your feet.


Stilettos are similar to pumps, but the heels are very slender, about the diameter of a pencil at the ground. Stiletto heels vary in height, with some as small as an inch to others reaching nine inches or more. Short-heeled stilettos are often called kitten heels.

Women love wearing stilettos because they give the illusion of an elongated, slimmer frame. They also alter your posture, flexing your calf muscles and making your bust and rear end more prominent. Not to mention, they can make any outfit look chic.

Like pumps, you can wear stilettos with almost anything, be it formal, casual or somewhere in between. Shorter stilettos can work well with mini and short dresses, as they make your legs look a million miles long. Be careful about pairing tall stilettos with short dresses, though, as you might show off more leg than you intended. When paired with a loose, free-flowing dress, tall stilettos also can have a more casual, laid-back appearance.

Pro tip: If stilettos are in your gameplan, consider investing in a pair of gel inserts. They remain invisible inside your shoes, and will reduce the stress placed on your feet. Be sure to hold the inserts up to your feet before you buy to ensure they will cover the whole area.

Peep Toe

Peep-toe shoes have bounced from popularity to obscurity and back in just a matter of decades. These shoes became a trend just after the French Revolution, when European women were daring enough to show off their toes. Later, peep toes became synonymous with beach style, becoming a two-in-one shoe for those who wanted both sandals and heels.

If you want to incorporate peep-toe shoes into your ensemble, the best rule to remember is bare toes go best with bare legs. So any short dress — with a hem at the knee or higher — can be a good match. For a more casual look, you can even trade out the heel for flat peep-toe shoes.

Love the idea of wearing peep toes, but hate showing off your legs? Try a pair of leggings, tights or opaque stockings underneath the dress. Then, find a pair of peep toes with a flat-buckled strap at the ankle, which works well with the straight edge of a pant hem.

Pro tip: For maximum comfort, opt for a heel shaped and scaled to the size of your feet and ankles. If you have larger feet, you may want to pick a sturdier heel. If you have smaller feet, you might choose a thinner heel.

Short Heel

Short heels are perfect for those who have a love-hate relationship with heels. Yes, you want the style and the height. But you don't like putting up with the aches or the trouble getting around. Besides better maneuvering, shorter, strappy heels can also accentuate a "leggy" look when paired with a shirt dress or mini.

What's great about short heels is you can wear them on almost any occasion, even a workday at the office. Whether you're heading to a networking event, a trip to the city or a night at the club, the right pair of short heels can work with any outfit.

For more stability, especially if you plan on walking a lot, opt for a chunkier heel, up to an inch or two wide. A thicker heel is also best for more conservative occasions, such as a dinner with the in-laws or a late-morning church service. If you want something a little more delicate, you can choose a slimmer heel, down to stiletto size.

Pro tip: Pay attention to width, not just length. If the balls of your feet feel squished inside a particular pair of shoes, don't immediately grab the next size up. Instead, ask the clerk if the shoe comes in a wider size.


Like most footwear, the initial purpose of boots was to protect the wearer's feet from nature's elements. Their popularity didn't become widespread until the 1970s, when the iconic white go-go boots premiered with ankle-, knee- and thigh-high options. With both heels and flats, go-go boots were the go-to for pairing for a mini-skirt.

Today, boots are a common sight in women's fashion, and you can wear them with casual, formal and business attire.

Some of the most popular types of boots include:

  • Ankle boots
  • Calf-length boots
  • Knee-length boots
  • Over-the-knee boots

Knee-length boots work great with short dresses, especially in cold weather. You can even pair them with a pair of dark tights. Brown and black boots are exceptionally versatile colors, as they pair well with a variety of outfits.

For ankle boots, try pairing a cowboy-inspired design with a flowy yellow fit-and-flare dress. Or, if you want to show off your silhouette, try a form-fitting maxi dress with a hem that reaches down to the ankle with a pair of bright, eye-catching ankle boots.

Pro tip: To accentuate your leg line, pair your dress with a pair of dark, long leggings and tuck them into your ankle boots. Or, use a cute pair of socks or leg warmers to layer over leggings.


Sandals are open footwear usually held to the foot with straps over the instep and sometimes around the ankle. Most sandals, whether they have a heel or not, leave most of the foot exposed, making them perfect for a trip to the beach. They're best to wear on casual occasions, though you might be able to get away with a high-heeled sandal for something more formal. 

Gladiator sandals, which are sexy and strappy, pair well with an A-line or shift dress with a hem that falls to the mid-thigh. This combination gives the illusion of longer, leaner legs. Slide sandals, which slip on and don't have any strap behind the ankle, can also be a super comfy addition to your wardrobe. They can work with a chic leather shift or even a casual jean shirt dress.

T-strap sandals, which incorporate a strap across the ankle and down to the toe, can put a sexy spin on any casual summer look. Or, if you're looking for the best shoes to wear with maxi dresses, you can opt for no-holds-barred flip-flops. 

Pro tip: While they may seem like a good deal, cheap sandals are often one step up from cardboard. Their poor workmanship will hurt your feet and will usually break apart after just one summer. Instead, choose a more durable shoe that will offer support and last multiple summers.


Flats, also called ballet shoes, feature a simple slipper style with no heel. They sometimes have a ribbon-like binding and often a decorative bow tie near the toe. With some styles, the fabric at the heel bunches together to hold tight against the ankle of the wearer.

These shoes get a bad rap, as they don't have the sensuality and glamour associated with high heels. But flats are the trifecta of shoes — a way to be comfortable, practical and stylish all at the same time. Plus, they can pair with a dress to suit almost any occasion.

Make flats formal with an ankle-length gown and pointed-toe flats. Or, pair a fitted sheath or shift dress with dark or neutral-toned tights and glittery ballet shoes. When paired with the right outfit, flats have a way of looking just as sleek and sophisticated as heels.

While you can wear black or nude flats with almost any outfit, the same is true in reverse. If you're wearing a neutral-colored outfit, play it up with some statement footwear, like leopard print or metallic slip-ons.

Pro tip: If you plan to wear flats, look for soft, flexible fabrics, like leather, which will naturally move with your feet. If you aren't interested in wearing leather, look for faux brands with a supple texture.


Wedges combine the height of a heel with the stability of a platform by using one piece of material — a wedge — for both the sole and heel. With the added support of the wedge, the shoe offers more support for the wearer, whether you plan to go dancing with friends or spend a quiet night with the family.

If you're looking for shoes to wear with sundresses, wedges can create the perfect bohemian look. Or, when paired with a knee-length, casual wrap-dress, a wedge heel can round out the perfect ensemble for a Fourth of July picnic in the park. Wedges also work great with dresses made with light and gauzy fabrics.

For the most part, you'll want to avoid pairing wedges with anything too fitted or short. The style works best with clothing that's free-flowing and airy.

Pro tip: Wedge heels with straps that buckle are typically more comfortable than the slip-on style. You should also look for wedges with a height lower than or up to your ankle when sitting on the floor. Anything higher will be more challenging to walk in.


Sneakers have a long history, but they weren't trendy until 1923, when Converse launched their All-Star line endorsed by basketball player Chuck Taylor. The shoe earned a reputation for its practical uses — hiking, running, playing sports, etc.

Today, people also wear sneakers as a fashion statement, though mostly a casual and laid-back one. You may think you can only wear them with shorts and jeans, but the right dress-sneaker combo can leave a lasting impression.

A brightly colored dress, such as a floral shirt dress or pink A-line dress, can look expertly put together with a pair of crisp white sneakers. For a chic look, dress up a flowy, calf-length dress in a knockout color with a couple of standard dark sneakers.

A casual, long-sleeved shirtdress paired with classic striped Adidas and a denim jacket can make you look like the epitome of style as you stroll across campus or run some last-minute errands. Or, make a statement by adding cute, lace-up Converse sneakers with a fitted cocktail dress.

Pro tip: When it comes to wearing sneakers with dresses, you can never go wrong with black or white. You don't want to ruin a classic look with the wrong color. You should also clean your sneakers regularly, as dirty white sneakers can detract from even the classiest outfit.

Tips for Selecting the Right Shoes

Whether you've already found the perfect pair of shoes, or you're still scratching your head over your choices, you can follow a few tips to make the selection process easier. Let the advice above guide you to narrow your focus and find the perfect shoes for your dress.

1. Try Both Shoes On

It may seem obvious, but the best way to ensure you pick the right shoes is to make sure they fit comfortably on your feet. Unfortunately, you can't always rely on buying the same size. Not only do your feet grow and change shape, but not all shoe manufacturers have the same standards. While you may find the ideal fit at a size nine with one brand, you might find you need a size down with another. To avoid any hassle, try shoes on at the store before you buy.

2. Think About Stability

Besides buying shoes that fit, another way to avoid foot pain is to buy shoes that provide stability. As a bonus, high-quality shoes will also last longer than cheaply made ones, offering a better investment. Check the shoe's materials, including the sole, insole, tongue and laces. Pay attention to the seams and whether they feel secure when you're walking. If the shoe feels flimsy, it's probably poorly made and won't last long. The lack of support will also lead to foot pain after you wear them.

3. Consider the Colors

Try to consider shoe colors that won't overshadow or clash with your outfit. For example, if you're wearing a dress with a bright, bold pattern, choose a more subdued shoe in subtle tones. Or, if you're wearing something with lots of sequins and sparkles, pair it with a shoe in a neutral or nude color. On the flipside, if your outfit is more reserved or neutral, you can always spice it up with a pair of brightly colored heels or flats.

4. Choose a Darker Shade

Don't even bother trying to match the color of your dress and shoes perfectly. It's almost impossible to do. Instead of buying an almost-match that looks out of place, buy a pair of shoes a shade darker than your outfit. The difference in color will be barely noticeable as part of your ensemble, but will prevent your color tones from clashing.

5. Avoid Over-Matching

There is such a thing as too much matching. You don't want to wear one solid color from head to toe. For example, if you're wearing an A-line dress in solid navy blue, try not to pair it with a blue pair of shoes. Instead, add variety to your ensemble with kitten heels in white or flats in a nude or pink color. Or, bring some color to an all-white outfit with a splash of lime-green pumps.

6. Think About the Season

One way to quickly narrow your shoe search is to consider the season. While you may love your peep-toe shoes, they may not be the best option for cold, snowy weather. Likewise, knee-high boots may not be comfortable in summer's heat and humidity. The dress you're wearing is one factor to consider, but you should also keep comfort in mind. Instead of kitten heels, pair that emerald wrap dress with dark tights and a pair of chocolate suede ankle boots.

7. Remember the Occasion

Other than your dress, one thing that should dictate your footwear is the occasion. While heels can be perfect for a night out or a party at the office, they won't work as well for a picnic in a grassy park. Similarly, while sandals are ideal at the beach or a meal at a restaurant, they can be a risk for squashed toes when you wear them for a night out dancing.

8. Incorporate Accessories

Matching your shoes with your accessories, like a purse, belt or necklace, is one of the oldest tricks in fashion. And there's a reason why — it works. Matching colors, especially in multiple pieces of your outfit, creates a sense of cohesion. Try to match your shoes with only one or two other items, such as your purse or belt. Any more than that can seem like too much.

Pairing Shoes With Dresses

When it comes to learning how to pick shoes to wear with a dress, remember, you don't have to follow the guidelines blindly. If you find a loophole that works, exploit it. Only you know your style, so it's up to you to choose which shoes will send the right message. 

Are you ready for a wild night out on the town? Or maybe you only want to have a quiet meal at a restaurant? No matter the occasion, there are plenty of shoes to choose from that will make your ensemble complete. Shop for your next favorite pair at Perfectly Priscilla. We feature a wide selection of on-trend women's shoe styles, from booties to wedges and everything in between. We also offer sizes from five to 11, so you'll be sure to find a size that fits you.

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