How to wear flat shoes with dresses: 5 chic outfits to copy

Despite what Sex and the City had us believe, you don’t need to wear heels to look smart and stylish, and we have the proof. Here are five dresses and flat shoes outfit combinations from fashion’s chicest street stylers that prove the staying power of comfortable footwear.

1. Dresses + ballet flats

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Olivia Palermo and model Alek Wek show how wearing ballet flats (preferably the Jimmy Choo variety) can look incredibly chic. A pointed toe or patent finish is key to this look, and the flat sole allows you to do a shorter dress length. And after their incredible comeback over the last year it’s safe to say they are also a great choice when it comes to trendy footwear.

-50%

Proenza Schouler

Slash ballerina shoes - women - CALFSKIN/Calf Leather/Polyurethane - 36 - Grey Gray

Delivery: free

$373.00 ~~$750.00~~

FARFETCH

-8%

Gucci

Horsebit-detail sandals - women - Leather/Patent Leather/Leather - 36.5 - Grey Gray

Delivery: free

$249.00 ~~$271.00~~

FARFETCH

-40%

Onitsuka Tiger

Mexico 66 TGRS sneakers - women - Artificial Leather/Rubber/Calf Leather - 37.5 - Pink

Delivery: free

$262.00 ~~$437.00~~

FARFETCH

-10%

Michael Michael Kors

Darrington ballet flats - women - Leather - 7.5 - Black

Delivery: free

$316.00 ~~$351.00~~

FARFETCH

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2. Combat boots

Jeremy Moeller/Getty Images

Pair a romantic dress with cool worker boots – the perfect way to add an effortless edge to your evening dresses.

Matisse Footwear

Womens Hunter Combat Boot by Matisse Footwear White

Sold out

$170.00

Matisse Footwear

Loewe

Leather Combat Boots - Black - IT 35 - Moda Operandi

Sold out

$690.00

Moda Operandi

Dear Frances

Tony Boot, Black

Sold out

$670.00

Dear Frances

Park Boot, Black

Sold out

$625.00

Dear Frances

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3. Sneakers

BERLIN, GERMANY - SEPTEMBER 07: Lois Opoku wearing a black leather jacket, a black dress and sneakers on September 07, 2021 in Berlin, Germany. (Photo by Jeremy Moeller/Getty Images)

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Berlin-based blogger Lois Opoku reminds us that everything looks cool with sneakers, even an oversized leather blazer paired with a cool t-shirt dress.

Veja

+ Net Sustain V-10 Leather Sneakers - White - IT36,IT37,IT38,IT39,IT40,IT41

Sold out

$165.00

NET-A-PORTER

adidas Originals

+ Net-a-porter Stan Smith Vegan Leather Sneakers - White - UK3.5,UK4,UK4.5,UK5,UK5.5,UK6,UK6.5,UK7,UK7.5,UK8,UK8.5,UK9

Sold out

$150.00

NET-A-PORTER

Alexander McQueen

Suede-trimmed Leather Exaggerated-sole Sneakers - White - IT35,IT35.5,IT36,IT36.5,IT37,IT37.5,IT38,IT38.5,IT39,IT39.5,IT40,IT40.5,IT41,IT41.5

Sold out

$590.00

NET-A-PORTER

Common Projects

Tournament Leather Sneakers - White - IT35,IT36,IT37,IT38,IT39,IT40,IT41,IT42

Sold out

$440.00

NET-A-PORTER

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4. Biker boots

NEW YORK, NEW YORK - SEPTEMBER 11: Allie Michler of Vogue wears a white blouse, blue jeans, and black flats at the Thom Browne show on September 11, 2021 in New York City. (Photo by Melodie Jeng/Getty Images)

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Vogue’s Market Editor Allie Michler is the epitome of looking chic without trying too hard in this always-cool combo of a white blouse, blue jeans, and black ballet flats.

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Tory Burch

Reva patent leather ballet flats Black

Delivery: Delivery costs apply

$273.00 ~~$455.00~~

Mytheresa

Kenneth Cole

Nolita Flat Black

Delivery: Delivery costs apply

$37.99

Rue La La

Stuart Weitzman

Black Round Toe Ankle Strap Pumps Size 39.5

Delivery: $15.00

$236.37

HEWI

BESTSELLER

Dolce & Gabbana

Leather Slingback Flat Black

Delivery: Delivery costs apply

$494.99

Rue La La

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5. Investment sandals

BERLIN, GERMANY - JULY 25: Tina Haase is seen wearing Nanushka dress in creme white, Jil Sander flats in black, Jacquemus bag, Chanel sunglasses on July 25, 2021 in Berlin, Germany. (Photo by Christian Vierig/Getty Images)

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German content creator Tina Hasse is the push we need to finally invest in a good quality pair of summer sandals. Her style of choice? A pair of slides from Jil Sander.