30 Ways Everyone's Styling Flats With Dresses in 2023

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 

Ballet Flats + Mini Slip Dress + Chunky Chain Necklace
Fashion influencer wearing chain necklace, slip dress, and Valentino flats



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. 

Ballet Flats + Maxi Linen Dress + Woven Tote Bag
Fashion influencer wearing ballerina flats with linen maxi dress and woven bag



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. 

2. Flatforms 

Flatform Sandals + Shearling Coat + Sweaterdress
Fashion influencer wearing sweater dress, shearling coat and shearling flatform shoes


Szymon Brzóska/The Style Stalker via @venswifestyle

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. 

Flatform Sandals + Leather Blazer + Slip Dress + Belt
fashion influencer wearing slip dress with leather blazer and flatform sandals



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. 

3. Loafers 

Loafers + Button-Front Dress + Shoulder Bag
Fashion influencer wearing button-up dress and loafers



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. 

Loafers + Button-Down Top + Black Minidress
Fashion influencer wearing button-down, leather dress and loafers



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

4. Flat Knee-High Boots 

Flat Knee-High Boots + Turtleneck Dress + Long Duster Cardigan + Belt
fashion influencer wearing duster cardigan, turtleneck dress and flat knee high boots



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. 

Flat Knee-High Boots + Minidress + Button-Down
Fashion influencer wearing flat knee high boots, buton-down and mini dress



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

5. Mary-Jane Flats 

Mary-Jane Flats + Strapless Maxi Dress
Fashion influencer wearing strapless maxi dress and mary jane shoes



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. 

Mary-Jane Flats + Turtleneck + Baby-Doll Dress
Fashion influencer wearing turtleneck underneath dress with mary jane shoes



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. 

6. Flip-Flops

Puff-Sleeve Dress + Flip-Flops + Straw Bag
Fashion influencer wearing white puff sleeve dress, and flat flip flop sandals



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. 

Flip-Flops + Maxi Dress + Leather Jacket + Shoulder Bag
Fashion influencer wearing leather moto jacket, maxi dress and flip flops



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. 

7. Chunky Sneakers 

Chunky Sneakers + Printed Mesh Dress + Oversize Tote Bag
Fashion influencer wearing mesh dress, chunky sneakers and oversized tote bag



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. 

Sneakers + Maxi Dress + T-Shirt + Sporty Sunglasses + Sling Bag
Fashion influencer wearing t-shirt layered under maxi dress with sneakers



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. 

8. Cowboy Boots

Cowboy Boots + Tank Dress + Oversize Blazer + Belt Bag
Fashion influencer wearing tank dress, oversize blazer, cowboy boots and belt



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. 

Cowboy Boots + Lace Dress + Shoulder Bag
Fashion influencer wearing lace dress and cowboy boots



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

9. Slides

Slides + Lace Slip Dress + Sunglasses
Fashion influencer wearing slip dress and slides



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. 

Slide Sandals + Blazer + Maxi Dress + Shoulder Bag
Fashion influencer wearing maxi dress with blazer and slides



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. 

10. Combat Boots

Combat Boots + Leather Trench + Knit Wrap Dress + Shoulder Bag
Fashion influencer wearing leather trench over sweater dress with combat boots



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. 

Floral Dress + Combat Boots + Shoulder Bag
Fashion influencer wearing floral wrap dress and combat boots



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. 

11. Strappy Flat Sandals 

Strappy Flat Sandals + Minidress + Blazer
Fashion influencer wearing blazer, mini dress, and strappy tie-up sandals



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

Strappy Flat Sandals + Strapless Poplin Dress + Woven Tote Bag
Fashion influencer wearing sun dress with straw bag and wrap up sandals



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. 

12. Oxfords 

Oxfords + Denim Button-Down Dress + Plaid Dress + Shoulder Bag
Fashion influencer wearing layered dresses and oxford flats



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. 

Oxfords + Oversize Button-Down + Sweater-Vest + Shoulder Bag
Fashion influencer wearing oversize button down and vest as dress with oxfords



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

13. Chelsea Boots

Chelsea Boots + Turtleneck + Floral Dress + Chain Necklace
Fashion influencer wearing turtleneck underneath a floral print dress with chelsea boots



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. 

Flat Knee-High Boots + Wool Blazer + Sweaterdress + Shoulder Bag
Fashion influencer wearing blazer over knit sweater dress with Chelsea boots



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. 

14. Chunky Sandals 

Chunky Sandals + Blazer + Maxi Slip Dress
Fashion influencer wearing pink blazer over pink maxi slip dress with dad sandals



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. 

Chunky Sandals + Printed Halter Dress
Fashion influencer wearing printed halter dress and dad sandals



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. 

15. High-Top Sneakers 

High-Top Sneakers + Cotton Poplin Dress + Shoulder Bag
Fashion influencer wearing white poplin dress with high top sneakers



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. 

Leather Jacket + Knit Dress + High-Top Sneakers



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.