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How to Wear Dresses with Flat Shoes: Seven Easy Outfits
Get dressed in seconds and keep comfortable on your feet—without sacrificing style.
Myth: Dresses don’t mix well with flats. Reality: When done right, pairing a dress with flat shoes is a Power Casual outfit formula that’s chic, easy, and can help you stay on your feet for hours on end.
Power Casual is our North Star when it comes to getting dressed these days. It’s a styling philosophy that mixes elevated pieces with more casual items in order to eliminate the need for separate “on duty” and “off duty” wardrobes. In execution, this could look like a blazer with jeans or—you guessed it—a tailored work dress paired with comfortable flats.
So how do you pull off this combination without looking frumpy or just downright confused? For the July edition of our Power Casual Report series, we put together a brief guide to help you choose flat shoes that won’t cramp your dress’s style—which you can put into practice whether you’re wearing a maxi dress, midi dress, or mini dress. Scroll to see all seven tips, featuring limited-edition dress styles from our very special Heritage Seven collection.
More of a pants person? Check out our guide to shoe-and-pant pairings.
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Seven Dress and Flats Outfits
Opt for Pointy
If it feels like your shoes are truncating your dress’s elongating silhouette, try pointed-toe flats rather than round-toe ballet flats. The sharp Rowan flats are a foolproof pairing for silhouettes like the Masha dress, which features a lengthening pencil skirt with subtle pleats. For an optional layer, go with our longest and most popular jardigan, the Merritt, to complement your dress’s below-the-knee hemline.
Go Nude
Wearing flats in a hue similar to your skin tone is another way to create length and keep the focus on your dress. The Toi dress is the perfect example of a style that can stand on its own alongside minimalist neutral flats, thanks to its impeccable tailoring and twirly skirt. Balance out your flowy bottom half with a super-lightweight cardigan, and top off this look with caramel earrings that pair back to your shoes.
Sandals for Summer
Sandals pair seamlessly with most dresses. Just make sure to select a polished style that’s made from high-quality materials to match the formality level of your dress. The low-key yet luxurious Italian leather Carter slides work perfectly with the classically tailored Jaycie dress. Add the sleek Parker earrings for good measure.
Short(ish) Dress, No Stress
Knee-length or above-the-knee hemlines give you a lot of leeway when it comes to flat footwear pairings. For whatever reason, shorter dresses just work with a wide range of shoe styles. So if you like options, pick up a style like the square-neck, slightly swingy Pauline dress, and go wild. The snake-print Rowan flats make an especially pretty pairing for the deep teal version of the Pauline, and this combination creates a stunning contrast alongside a cream jacket and matching statement earrings.
Fancify Your Flats
An elevated look doesn’t require shoes that are literally elevated. Flats that feature a metallic finish or a bit of embellishment can up your fancy factor just as much as a sky-high stiletto. Next time you have a special event that’s sure to involve a lot of standing, pair the party-ready Taylor dress with an eye-catching flat. Our top picks include the Rowans in silver or Prosecco. Tie the look together with coordinating earrings, and add a bit of edge with the vegan leather Nicky jacket.
Play with Pattern
Incorporating pattern is another way to step up your flats game, especially when wearing a solid black dress that welcomes the addition of a bold accessory. Try the leopard-print Grace loafers with the Felisa dress, which features clean lines and cap sleeves, and layer on a cropped jacket during the cooler months. Complete your mostly black look with gold accessories like the shiny Claressa hoops and dainty Single Bezel necklace.
Keep It Casual
Conversely, flat shoes can help you play up your dress’s more casual side—allowing you to reframe your elevated dresses for everyday wear. The wrap-style Tory dress fits right in at the office or a cocktail party, but when paired with leather sneakers and hoop earrings, it becomes an effortlessly cool Power Casual piece.
