30 Ways Everyone's Styling Flats With Dresses in 2023

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When Victoria Beckham said, "I can't concentrate in flats," I felt that in my soul. Before it was even deemed "apropos," I tried to walk in heels at a very young age. Like Beckham, I've always been an avid collector of heels and have rarely worn flats. But things have changed over the past few years, and I've slowly come around to the idea of pushing aside my heels occasionally for a pair of flats. In part, that shift is due to the rise of cool shoe trends (e.g., ballet flats and cowboy boots) that have made embracing this style more tantalizing. But it's also because I've noticed a styling trend among the fashion set that can't be ignored: flats worn with dresses. 

As someone who loves a good dress just as much as heels, I was dubious when my feed began to be flooded with the styling trend. However, after further research, I've realized that styling flats with dresses is the move in 2023. And to prove that point, I've found 30 outfit ideas that show how to wear flats with a dress. Plus, I've identified the best shoe styles to wear with dresses. Whether you're a die-hard flats fan or need to give your feet a break, these styling pairings will come in handy all year. 

1. Ballet Flats 

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Ballet Flats + Mini Slip Dress + Chunky Chain Necklace
(Image credit: @emilisindlev)

There's a common misconception that you "must" wear a pair of heels to look sultry for a date night, but the look above proves otherwise. Pair a mini slip dress with studded ballet flats and chunky jewelry for a balmy evening look. 

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Ballet Flats + Maxi Linen Dress + Woven Tote Bag
(Image credit: @chiarasatelier)

Another common misconception is that ballet flats are made for the fall and spring—that couldn't be further from the truth. If you want to avoid wearing a pair of sandals with your favorite maxi dress in the summer, try pairing it with ballerina flats and a fun bag. 

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2. Flatforms 

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Flatform Sandals + Shearling Coat + Sweaterdress

For transitional weather, strategic styling is the easiest way to get more use out of your platform sandals. Pair them with cold weather–friendly staples like a sweaterdress and shearling coat. 

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Flatform Sandals + Leather Blazer + Slip Dress + Belt
(Image credit: @shhtephs)

Dresses and flatform shoes can be worn beyond the summertime if you get creative with your layering. Don't be afraid to throw on a pair of socks or pair a leather blazer with a slip dress to make these pieces work between seasons. 

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3. Loafers 

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Loafers + Button-Front Dress + Shoulder Bag
(Image credit: @emmanuellek_)

The key to achieving that French je ne sais quoi? Don't be afraid to pair ultra-romantic pieces with tougher ones—e.g., a pair of loafers with a button-front dress. 

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Loafers + Button-Down Top + Black Minidress
(Image credit: @xbibigul)

Make your favorite black dress transition into the daytime by wearing it with a button-down, knee-high socks, and loafers. 

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4. Flat Knee-High Boots 

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Flat Knee-High Boots + Turtleneck Dress + Long Duster Cardigan + Belt
(Image credit: @oliviafaeh)

For moderate winter days, you don't have to shy away from wearing a dress. Pair your favorite flat knee-high boots with a turtleneck dress and a long duster cardigan layered over it. 

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Flat Knee-High Boots + Minidress + Button-Down
(Image credit: @slipintostyle)

Who says you can't wear boots year-round? Try pairing flat knee-high boots with a minidress for a simple yet stylish look. 

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5. Mary-Jane Flats 

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Mary-Jane Flats + Strapless Maxi Dress
(Image credit: @deborabrosa)

Mary-Jane shoes are beginning to trend again, and I can't think of a better way to style them this year than with a simple strapless maxi dress. 

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Mary-Jane Flats + Turtleneck + Baby-Doll Dress
(Image credit: @pia_mbd)

On crisp days when you can't get away with a flowy maxi dress, don't be afraid to play with layering. Throw a turtleneck underneath a baby-doll dress, and pair your shoes with thick socks to get the same dolled-up feel while keeping warm. 

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6. Flip-Flops

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Puff-Sleeve Dress + Flip-Flops + Straw Bag
(Image credit: @styleidealist)

Call it cliché, but you can never go wrong with donning a puff-sleeve white dress, especially when it's paired with flip-flops and a woven bag. 

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Flip-Flops + Maxi Dress + Leather Jacket + Shoulder Bag
(Image credit: @daniellejinadu)

Another way you can get away with wearing your flip-flops and a dress on a chilly day all comes back to layering and coverage. Opt for a maxi dress styled with a leather jacket, and you'll have the best of both worlds. 

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7. Chunky Sneakers 

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Chunky Sneakers + Printed Mesh Dress + Oversize Tote Bag
(Image credit: @kateemao)

Just because you're not wearing sky-high heels doesn't mean you can't up the cool factor. If you opt for a unique printed mesh dress styled with chunky sneakers and an oversize tote bag, you'll be flyin' above them all. 

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Sneakers + Maxi Dress + T-Shirt + Sporty Sunglasses + Sling Bag
(Image credit: @noore)

Again, the key to making a flats-and-dress pairing feel fresh comes back to the styling. Try pairing chunky sneakers with a maxi dress and sporty sunglasses—it's sure to be the breath of fresh air you've been craving. 

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8. Cowboy Boots

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Cowboy Boots + Tank Dress + Oversize Blazer + Belt Bag
(Image credit: @simplytandya)

The fashion set continues to be giddy about cowboy boots. But if you're afraid of feeling too Western inspired when wearing these shoes, take a cue from the look above. Keep your styling minimal by pairing these flat boots with a tank dress, oversize blazer, and belt bag. 

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Cowboy Boots + Lace Dress + Shoulder Bag
(Image credit: @alyssainthecity)

Want to lean into the Western aesthetic fully? Try pairing cowboy boots with a vintage-looking lace dress and shoulder bag. 

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9. Slides

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Slides + Lace Slip Dress + Sunglasses
(Image credit: @greceghanem)

Do you know those insufferable balmy days when you dread picking an outfit because it's so warm? Don't sweat. Keep it simple and opt for a lace slip dress styled with flat slides and great shades. 

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Slide Sandals + Blazer + Maxi Dress + Shoulder Bag
(Image credit: @gosiaboy)

Looking for an outfit idea that's warm weather friendly and work friendly? Look no further than the ensemble above. Pairing a maxi dress with a blazer and polished slides will impress all your co-workers. 

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10. Combat Boots

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Combat Boots + Leather Trench + Knit Wrap Dress + Shoulder Bag
(Image credit: @astyleedit)

Combat boots can be polished. Case in point: the outfit above. Simply style the flat boots with a knit wrap dress, leather trench coat, and shoulder bag. 

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Floral Dress + Combat Boots + Shoulder Bag
(Image credit: @tamaramory)

That floral dress in the back of your closet that's lost its edge? Instead of donating it, try styling it with combat boots and a shoulder bag. It's a pairing that's sure to make florals feel groundbreaking. 

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11. Strappy Flat Sandals 

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Strappy Flat Sandals + Minidress + Blazer
(Image credit: @oumaymaboumeshouli)

Looking for a way to dress up the flat strappy sandals in your closet? Try pairing them with a minidress and blazer. 

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Strappy Flat Sandals + Strapless Poplin Dress + Woven Tote Bag
(Image credit: @monikh)

Instead of trying to dress up this relaxed shoe style, you can lean into the chill vibe completely. Pair it with a strapless poplin dress and a woven tote bag for the perfect off-duty look. 

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12. Oxfords 

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Oxfords + Denim Button-Down Dress + Plaid Dress + Shoulder Bag
(Image credit: @hodanyousuf)

Preppy-inspired pieces are a huge trend on social media, so why not test them out this year? Opt for a pair of oxfords styled with a gingham dress to achieve the aesthetic easily. 

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Oxfords + Oversize Button-Down + Sweater-Vest + Shoulder Bag
(Image credit: @mobinapeiman)

You also can achieve the "preppy" look by styling an oversize button-down with an oversize sweater-vest and oxfords. 

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13. Chelsea Boots

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Chelsea Boots + Turtleneck + Floral Dress + Chain Necklace
(Image credit: @meganadelaide)

Most people own at least one pair of functional Chelsea boots or lug-sole ankle boots that are more functional than fashionable. But if you want to make them feel like the latter, try wearing them with a funky printed dress styled over a turtleneck. 

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Flat Knee-High Boots + Wool Blazer + Sweaterdress + Shoulder Bag
(Image credit: @eniswardrobe)

If you prefer to keep your ensembles minimal, then you'll want to screenshot the look above. Pairing a thick wool blazer with a sweaterdress and Chelsea boots makes for a fail-proof 'fit every time. 

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14. Chunky Sandals 

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Chunky Sandals + Blazer + Maxi Slip Dress
(Image credit: @fiahamelijnck)

Consider this outfit proof that chunky sandals can be—dare I say—pretty. Pairing the "ugly" flats with a pink blazer and pink satin maxi slip dress will prove the point. 

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Chunky Sandals + Printed Halter Dress
(Image credit: @chainkyr)

The beauty of this flat shoe style is that it's effortless. You can pair it with a lightweight printed halter dress and head out the door with no doubt that you look good. 

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15. High-Top Sneakers 

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High-Top Sneakers + Cotton Poplin Dress + Shoulder Bag
(Image credit: @michellaccc)

If you've made it this far in the story, then you've hopefully concluded by now that the key to pulling off flats and dresses together is all about embracing unique pairings. A cotton poplin dress styled with designer high-top shoes (see the look above) is a prime example of just that. 

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Leather Jacket + Knit Dress + High-Top Sneakers
(Image credit: @georgia_3.0)

Consider the outfit above final proof that flats and dresses are a fire pairing to try at home. Whether you re-create the outfit above or any of the ensembles in this story, it's clear that this is one pairing that will continue to be popular all year long.

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Next: 15 Dress Styles Fashion People Wear Over and Over Again

Jasmine Fox-Suliaman
Editor

Jasmine Fox-Suliaman is a fashion editor living in New York City. What began as a hobby (blogging on Tumblr) transformed into a career dedicated to storytelling through various forms of digital media. She started her career at the print publication 303 Magazine, where she wrote stories, helped produce photo shoots, and planned Denver Fashion Week. After moving to Los Angeles, she worked as MyDomaine's social media editor until she was promoted to work across all of Clique's publications (MyDomaine, Byrdie, and Who What Wear) as the community manager. Over the past few years, Jasmine has worked on Who What Wear's editorial team, using her extensive background to champion rising BIPOC designers, weigh in on viral trends, and profile stars such as Janet Mock and Victoria Monét. She is especially interested in exploring how art, fashion, and pop culture intersect online and IRL.