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11 Best Shoes to Wear With Dresses

The streets of New York are currently a boiling 90 degrees and for the past two weeks, it hasn’t let up. The only solution? Staying indoors when possible, running into air-conditioned stores for relief whilst commuting, and wearing dresses any- and everywhere. (Who wants their clothes glued to their skin in this sticky weather?)

Sure, summer is the szn when you’re on the hunt for affordable dresses à la Amazon but once you’ve got the clothes, what about the shoes? I love creating stylish moments with dresses and the season’s latest trending footwear. For example, I would wear ballet flats or Mary-Janes with a coquette-aesthetic dress. As for a maxi dress, I would easily wear sneakers or platform sandals. No matter the hemline or material you’re wearing, the ultimate footwear guide is right here (and yes, kitten heels and chunky kicks are on the list)! Take a scroll at some of my fave combos below.

A Baby Doll Dress + Mary Janes

street style day 1 new zealand fashion week 23 kahuria

Ronald Rieza//Getty Images

How cute will you be in a baby doll dress and the ever-so classic Mary Jane shoe? The absolute cutest, I assure you.

Shop the Baby Doll Dress + Mary Janes:
Square-Toe Mary-Jane (Margot Mary-Jane)
Vivaia Square-Toe Mary-Jane (Margot Mary-Jane)
Kali Tuck Floral Off The Shoulder Minidress
Bardot Kali Tuck Floral Off The Shoulder Minidress
Patent Crossover-Strap Block-Heel Mary Janes
Charles & Keith Patent Crossover-Strap Block-Heel Mary Janes

A Knit Dress + Cowboy Boots

street style berlin may, 2022

Jeremy Moeller//Getty Images

Knit dresses are calling your name this fall and spring and I hope you answer with none other than an unexpected cowboy boot. Keep heads turning and compliments rolling in with a metallic design!

Shop the Knit Dress and Metallic Boots:
Dagget Western Boot
Jeffrey Campbell Dagget Western Boot

Now 50% Off

Crochet Knit Mini Dress
Fabumily Crochet Knit Mini Dress
Knox Metallic Western Boot
Azalea Wang Knox Metallic Western Boot

Now 24% Off

A Shirt Dress + Strappy, Kitten Heels

fashion photo session in paris may 2021

Edward Berthelot//Getty Images

A shirtdress is an easy way to look pulled together for the day, but you can instantly elevate the casual aesthetic with strappy, kitten heels. It just screams (or purrs?) that you’re giving an immediate slay.

Shop the Shirt Dress + Strappy, Kitten Heels:
Kitten Heel Metallic Sandals
Zara Kitten Heel Metallic Sandals
Poplin Shirt Dress
Good American Poplin Shirt Dress
Women's Heloise Strappy Mid Heel Sandals
SCHUTZ Women's Heloise Strappy Mid Heel Sandals

A Pocketed Dress + Gold Sandals

fashion photo session in paris march 2021

Edward Berthelot//Getty Images

Just about everyone squeals when they discover their dress has secret pockets, but while that’s always a sweet surprise, it’s nice to know you have those pockets for sure. I love a cargo dress for this reason. And gold, barely there sandals will complement this look so well.

Shop the Pocketed Dress + Gold Shoes:
Halsey Barely There Heeled Sandals
ASOS DESIGN Halsey Barely There Heeled Sandals
Summer A-Line Dress
Alyweatry Summer A-Line Dress
Lace Up Stiletto High Heel Sandals
Liliana Lace Up Stiletto High Heel Sandals

Now 18% Off

A Statement Dress + Chunky Sneakers

street style berlin fashion week ss24 july 11, 2023

Streetstyleshooters//Getty Images

Ofc, you need a statement dress and chunky sneakers! The above pair from Luis Vuitton is a definite splurge, but if you’re stressing about that, we have a list of affordable sneakers to wear with dresses right here for a just as cool vibe.

Shop the Metallic Dress + Chunky Sneakers:
AL8 Sneaker - Women's
Nike AL8 Sneaker - Women's
Prong Strapless Minidress
Rick Owens Prong Strapless Minidress
Saga 130 Sneakers
Saga 130 Sneakers

A Neutral Dress + Block Heels

street style berlin april, 2024

Jeremy Moeller//Getty Images

Bring some shine into beige or brown outfit moment with some patent-leather block heels (pointed or square-toe, you take your pick)!

Luccie Pointed Toe Pump in Dark Red
Marc Fisher LTD Luccie Pointed Toe Pump in Dark Red
Slinky Knot Detail Cut Out Midi Dress in Mocha
ASOS DESIGN Slinky Knot Detail Cut Out Midi Dress in Mocha
Steffie Bow Detail Mid Block Heeled Shoes
ASOS DESIGN Steffie Bow Detail Mid Block Heeled Shoes

Now 35% Off

A Slip Dress + Slouchy Boots

street style paris fashion week womenswear springsummer 2023 day four

Edward Berthelot//Getty Images

This outfit combo is the secret to a sultry spring and summer. This pink and black moment is edgy-Barbie-coded.

Shop the Slip Dress + Slouchy Boots:
Slouchy Boots in Tan
Bershka Slouchy Boots in Tan

Now 55% Off

Cowl Neck Satin Slipdress
Open Edit Cowl Neck Satin Slipdress
Vector Boots
Steve Madden Vector Boots

Now 25% Off

A Crochet Dress + Loafers

street style paris fashion week menswear springsummer 2023 day two

Christian Vierig//Getty Images

For the days you need a little breeze to kiss your skin, crochet dresses are the best choice. Typically, I would say to wear ’em with sandals to give your dogs some air too, but this loafer combo just works, right?

Shop the Crochet Dress + Loafers:
Hines Loafer
Dolce Vita Hines Loafer

Now 43% Off

Sweater Dress
PQ Swim Sweater Dress
Linnie Fray Loafer
Sam Edelman Linnie Fray Loafer

A Muted Dress + Bold Pumps

street style day 5 australian fashion week presented by pandora 2024

Hanna Lassen//Getty Images

Monotone on top, bold on the bottom. Let your footwear do all the talking for this outfit masterpiece. Bonus points if your pumps have a cool design!

Shop the Muted Dress + Bold Pumps:
Sedona Pointed Toe Pump
Steve Madden Sedona Pointed Toe Pump
Tahlia Dress in Yellow
SNDYS Tahlia Dress in Yellow
Pandora Pump
Ninety Union Pandora Pump

A Bright, Striped Dress + Combat Boots

street style berlin february 15, 2021

Jeremy Moeller//Getty Images

Good juxtaposition is wearing a colorful knit dress with heavy combat boots. It shows you’re a tough one that loves to have some fun, ya know?

Shop the Striped Knit + Combat Boots:
Black Knee High Boots
DREAM PAIRS Black Knee High Boots
Dana Dress Multi Bayadere Stripe
STAUD Dana Dress Multi Bayadere Stripe
Imogen Chunky Platform Knee-High Boots
Charles & Keith Imogen Chunky Platform Knee-High Boots

A Minidress + Thigh-High Boots

street style day 4 copenhagen fashion week autumnwinter 2020

Jeremy Moeller//Getty Images

This has to be the most obvious, top-tier, match-made in heaven! Gotta love when the short hemline meets the top of some very extra boots. Statement = made.

Shop the Mini Dress + OTK Boots:
Ronettes Over-The-Knee Boot
London Rag Ronettes Over-The-Knee Boot

Now 15% Off

Plus Mocha Bardot Ruffle Detail Shift Dress
Plus Mocha Bardot Ruffle Detail Shift Dress

Now 50% Off

Genna 60 Leather Thigh Boots
STUART WEITZMAN Genna 60 Leather Thigh Boots
Headshot of Tarah-Lynn Saint-Elien

Tarah-Lynn Saint-Elien is the fashion editor at Cosmopolitan, writing weighty and witty stories that run the gamut of gushing over Zendaya to convincing you of everything you need in your closet! She began her journey in the industry with a fashion and faith blog and an internship at Elle.com almost 10 years ago. Since then, she's also served as the style editor at The Haitian Times. The Haitian-American pageant queen is a Syracuse Masters graduate and the author of two books, including: Claim Your Crown. Follow her on Instagram and Twitter: @iamtarahlynn

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