Shoes to Wear with every type of dresses
While we’re quick to cover the latest trends across both wardrobe items, we thought we’d go back to basics and have a look at the shoes that always work with dresses. As such, we can conclude that there are eight key footwear styles that seem to suit dresses more than other shoe types.
Chances are you’ll already own some (if not all) of the shoes on our list, but that’s the beauty of taking a step back from the noise of the trends and instead focusing on timeless buys. Keep scrolling to see the shoes to wear with dresses this season and beyond.
1. BLOCK HEELS
Style Notes: Sylvie’s chic block-heel shoes will bestow any dress with easy French flair. This Gallic girl favours wearing them with minimalist midi dresses. Simple, yet so effective.
Shop Block Heels:
MANGO
Block-Heel Sandals
£46
You’ll wear these all spring and summer long.
REFORMATION
Margarita Slingback Heel
£298
I can’t believe how premium these look, and they also come in nude and silver.
GUCCI
Women’s Horsebit Slingback
£660
These are a timeless classic.
2. TRAINERS
Style Notes: In my opinion, trainers and dresses look their coolest when you opt for a simple dress paired with chunky running shoes or the most recent popular style, brights!
Shop Trainers:
ADIDAS ORIGINALS
Handball Spezial Suede Sneakers
£85
Coloured Adidas are selling out so fast, but these are still in stock—grab them while you can.
NEW BALANCE
550 C Sneaker
£130
The chunkier, the better.
LOEWE
Flow Logo-Appliquéd Shell, Leather and Suede Sneakers
£595
A high fashion classic that will go with just about every dress in your wardrobe.
3. TAN OR BEIGE BOOTS
Style Notes: While black boots also look excellent with dresses (especially in winter), tan and nude boots serve as a welcome change in spring. Their softer hue makes them less harsh when worn with pastel or white dresses.
Shop Tan Boots:
& OTHER STORIES
Classic Leather Ankle Boots
£165
These would look so good with a long flowing skirt or with blue jeans.
PARIS TEXAS
Stiletto Suede Knee Boots
£620
These would look so good with mini or maxi dresses.
STAUD
Wally Suede Knee Boots
£475
These are just so sleek.
4. SLINGBACKS
Style Notes: Slingbacks are an eternally chic option that fashion people have been reaching for more frequently in recent months. The refined shape and classic silhouette instantly elevates even the simplest dresses.
Shop Slingbacks:
ARKET
Slingback Leather Pumps
£189
Style with a classic LBD or a tailored set.
AEYDE
Melia Buckled Metallic Leather Slingback Pumps
£325
While these come in an array of shades, this silver style is going to be my new party go-to shoe.
REFORMATION
Wilder Slingback Heel
£298
I’ve been dreaming about this pair.
5. MARY JANES
Style Notes: When it comes to which shoes to wear with dresses, Mary Janes are a popular choice. The heeled styles gives you a vintage feel but flat versions are having such a moment right now.
Shop Mary-Janes:
AEYDE
Uma Leather Mary Jane Ballet Flats
£295
I love these in cream, but they also come in plenty of other tempting hues.
REFORMATION
Bethany Ballet Flat
£268
Burgundy is the tone to own this season.
JIMMY CHOO
Elisa 45
£675
I must have these.
6. TRACK-SOLE BOOTS
Style Notes: Chunky track-sole boots defined our winter wardrobes, but don’t pack them away just yet. With British weather consistently unpredictable you’ll appreciate this pair year round. Right now, Instagram’s most stylish people are donning chunky iterations with just about every dress you can think of.
Shop Track-Sole Boots:
ARKET
High-Shaft Chelsea Boots
£199
You’ll wear these for the rest of the year.
GANNI
+ Net Sustain Paneled Recycled-Leather Chelsea Boots
£345
These have been favourites for a couple of years now.
ISABEL MARANT
Ceilee Leather Chelsea Boots
£590
Such a great go-with-everything pair.
7. FINE-STRAP HEELS
Style Notes: Having been the shoes a couple of seasons ago, fine-strap sandals are set to make a strong comeback this year. As they’re the perfect antidote to statement outfits, it’s little wonder influencers keep wearing them with punchy print midi dresses to make sure all eyes are on the dress.
Shop Strappy Heels:
NEOUS
Ibor Leather Slingback Sandals
£495
These are unbelievably elegant.
BOTTEGA VENETA
Leather Sandals
£710
You’ll find every excuse to wear these.
MANGO
Strappy Heeled Sandals
£36
For those who like the extra height.
8. Loafers
Style Notes: Adding a preppy feel to any dress style, you can always count of a pair of sleek loafers to compliment a great dress. Emmanuelle goes one step further and adds cool-girl white socks
Shop Loafers:
JIGSAW
Frame Leather Loafer in Black
£130
I love the long, sleek silhouette. of these minimalist loafers.
GUCCI
Horsebit Loafer
£810
Chunky pairs look effortlessly cool.
COS
Leather Loafers
£115
.
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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.
How to Style a Maxidress for Every Mood and Occasion
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
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
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
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
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
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
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.
How to Clean White Shoes and Make Them Look Brand New
A Blazer Dress
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
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
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
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
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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