What Shoes to Wear With Every Type of Dress - InStyle

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Growing up, I had a rigid sense of style. I’d convinced myself that sneakers were for T-shirts and jeans, and heels were to be worn exclusively with dresses and skirts. Of course, that all changed when I saw Sandra Bullock in a maxi skirt and tennis shoes in a scene from Practical Magic.

Everything about the outfit was groundbreaking; it was cute, it was comfortable, and it was very '90s. To borrow a line from another '90s queen, Carrie Bradshaw, I couldn't help but wonder, what other shoe pairing possibilities awaited me? And just like that, I began experimenting, making it my mission to figure out what shoes to wear with every type of dress.

The answer: Whatever shoes you want, really. Time and again, we all could use a gentle reminder that there are no rules in fashion. When you look good, you feel good, and personal style is just that — personal. That said, there’s no denying that, objectively, some shoes tend to work better with particular silhouettes and hemlines. But you’ll never know what works and what doesn’t until you play around with your wardrobe — or you ask a professional stylist for their input.

We did the latter for you. Up ahead, we’ve paired 12 styles of dresses with the types of shoes stylists think go best with them.

A Minidress

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Wear with: Ballet flats

Are you shocked? You might think a pair of strappy heels would be the perfect pairing for a mini, especially for petite women looking to elongate their legs (and they are!), but because French girl fashion is trending right now, stylist and style expert, Naina Singla says ballet flats are the way to go. Not to mention, because the balletcore trend is still popular, it drives home Singla’s hot take that these shoes with a mini dress is a combination you must try.

A Midi Dress

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Wear with: An open-toe kitten heel

Personal stylist and style coach Samantha Dawn is an advocate for the midi dress-open-toe kitten heel pairing, particularly if the shoes boast an ankle strap, as she tells InStyle this detail makes a huge impact on the overall look. “The ankle strap makes the transition from the dress to the ankles more seamless and the kitten heel makes the dress appear more classy,” Dawn explains, adding that the open toe also “creates fun dimensions for the entire outfit.”

A Maxidress

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Wear with: Strappy block heels

Rather than risk a stiletto heel catching the hem of a maxidress, Dawn recommends choosing a blocked, strappy heel for a bit more stability. “Blocked heels have more durability and can give someone more balance if they don't like skinny heels,” Dawn explains, adding that strappy detailing will still lend the look a fun and playful vibe.

Full Skirt

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Wear with: Pointed-toe pumps or heeled sandals

Voluminous dresses are fun and bold, but because the make a statement all their own, style therapist Christina Stein stresses daintier pairs of shoes will help balance out the billowing skirt. Her recommendation? A closed pointed-toe pump or open-toe heel.

A Cocktail Dress

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Wear with: Open-toe heeled sandals

Pro tip: When styling cocktail dresses for clients, Stein tells InStyle she’ll typically go for an open-toe heeled sandal, and color match the shoe with the person she’s dressing’s skin tone. “It makes your legs look longer and gives cohesion to a look.” We also like matching the shoe to the dress, like Joey King's look here.

A Slip Dress

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Wear with: Anything and everything

Slip dresses will be your best friend on days you’re busy or just can’t be bothered to put together an intricate outfit. Not only are they a one-and-done option, but they also pair with practically any shoe. Personal stylist Allie McKenna raves she’s worn slip dresses with sneakers, combat boots, mules, and loafers, too. You can make most footwear work with the style, she says, it just depends on the occasion, as well as your use of accessories.

“If you’re wearing a slip dress with sneakers, it’s important to add other casual elements to it like a T-shirt underneath,” McKenna explains. “When I wore the slip dress with mules, I paired it with dainty jewelry and a black leather shoulder bag." For loafers, she suggests similar styling as sneakers: "There should be another casual element to the look, however you can also wear it with a blazer to complement.”

A Button-Down Shirtdress

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Wear with: White sneakers

Button-down shirtdresses toe the line between dressy and casual. They’re a put-together piece, but emit a relaxed vibe you want to transfer over to your feet, too. To do so, Dawn recommends a fresh pair of clean, white sneakers to maintain that “relaxed, vacation-mode” feel throughout the look.

A Blazer Dress

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Wear with: Kitten heels

Whether you’re donning a blazer dress to the office or dinner, Dawn suggests opting for a kitten heel to emphasize the style’s powerful energy. Plus, given that tall heels aren’t always comfortable, Dawn notes a lower heel will give off the same elegance as a stiletto, but won’t hurt your feet in the process.

A Denim Dress

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Wear with: Cowboy boots, sneakers, or loafers

If you haven’t leaned into the coastal cowgirl aesthetic yet, McKenna tells InStyle a denim dress and a pair of cowboy boots is a great place to start. But because denim is such a casual fabric, if you aren’t going for something super trendy, the stylist is also big on styling this type of dress with a trusty pair of sneakers. If you’re looking to dress up a denim number, McKenna says, “a gold loafer block heel will give it a slightly fancier look.”

A T-Shirt Dress

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Wear with: Combat boots

Dawn tells InStyle that T-shirt dresses and combat boots go together like peanut butter and jelly, and I concur. An ankle-length style will give the everyday dress and edgier, street-style look,  but whatever variation of combat shoe speaks to your aesthetic, the goal is to have the combat boot “give the look a more badass vibe rather than a boring 'I just got out of bed' look,” Dawn explains.

A Sundress

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Wear with: Loafers

A classic shoe for a classic dress. Singla tells InStyle that although loafers don’t always come to mind when styling a dress, “they can create an unexpected and contrasting outfit that looks polished when put together.”

A Babydoll Dress

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Wear with: Loafers

Personal stylist Jordan Stolch says that in addition to loafers being an excellent pairing for sundresses, she’d also opt for this style of shoe when putting together a look centered around a babydoll dress. “The look is polished and versatile, taking you from errands to afternoons with girlfriends, and bound to rack up a lot of compliments along the way.”

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