30 Ways Everyone's Styling Flats With Dresses in 2024

When Victoria Beckham said, "I can't concentrate in flats," I felt that in my soul. 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 occasionally pushing aside my heels 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.

I love a good dress just as much as I love heels, so I was dubious when the styling trend started flooding my feed. However, after further research, I've realized that styling flats with dresses is the move in 2024. 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.

Ballet Flats 

What You'll Need: Ballet Flats + Mini Slip Dress + Chunky Chain Necklace

Styling Notes: 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.

What You'll Need: Ballet Flats + Maxi Linen Dress + Woven Tote Bag

Styling Notes: 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.

Flatforms

What You'll Need: Flatform Sandals + Shearling Coat + Sweaterdress

Styling Notes: 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.

What You'll Need: Flatform Sandals + Leather Blazer + Slip Dress + Belt

Styling Notes: 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.

Loafers

What You'll Need: Loafers + Button-Front Dress + Shoulder Bag

Styling Notes: 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.

What You'll Need: Loafers + Button-Down Top + Black Minidress

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

Flat Knee-High Boots 

What You'll Need: Flat Knee-High Boots + Turtleneck Dress + Long Duster Cardigan + Belt

Styling Notes: For moderate-weather 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.

What You'll Need: Flat Knee-High Boots + Minidress + Button-Down

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

Mary Jane Flats 

What You'll Need: Mary Jane Flats + Strapless Maxi Dress

Styling Notes: 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.

What You'll Need: Mary Jane Flats + Turtleneck + Baby-Doll Dress

Styling Notes: 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.

Flip-Flops

What You'll Need: Puff-Sleeve Dress + Flip-Flops + Straw Bag

Styling Notes: 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.

What You'll Need: Flip-Flops + Maxi Dress + Leather Jacket + Shoulder Bag

Styling Notes: 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.

Chunky Sneakers 

What You'll Need: Chunky Sneakers + Printed Mesh Dress + Oversize Tote Bag

Styling Notes: 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.

What You'll Need: Sneakers + Maxi Dress + T-Shirt + Sporty Sunglasses + Sling Bag

Styling Notes: 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.

Cowboy Boots

What You'll Need: Cowboy Boots + Tank Dress + Oversize Blazer + Belt Bag

Styling Notes: 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.

What You'll Need: Cowboy Boots + Lace Dress + Shoulder Bag

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

Slides

What You'll Need: Slides + Lace Slip Dress + Sunglasses

Styling Notes: 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.

What You'll Need: Slide Sandals + Blazer + Maxi Dress + Shoulder Bag

Styling Notes: 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.

Combat Boots

What You'll Need: Combat Boots + Leather Trench + Knit Wrap Dress + Shoulder Bag

Styling Notes: 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.

What You'll Need: Floral Dress + Combat Boots + Shoulder Bag

Styling Notes: 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.

Strappy Flat Sandals 

What You'll Need: Strappy Flat Sandals + Minidress + Blazer

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

What You'll Need: Strappy Flat Sandals + Strapless Poplin Dress + Woven Tote Bag

Styling Notes: 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.

Oxfords 

What You'll Need: Oxfords + Denim Button-Down Dress + Plaid Dress + Shoulder Bag

Styling Notes: 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.

What You'll Need: Oxfords + Oversize Button-Down + Sweater-Vest + Shoulder Bag

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

Chelsea Boots

What You'll Need: Chelsea Boots + Turtleneck + Floral Dress + Chain Necklace

Styling Notes: 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.

What You'll Need: Flat Chelsea Boots + Wool Blazer + Sweaterdress + Shoulder Bag

Styling Notes: 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.

Chunky Sandals 

What You'll Need: Chunky Sandals + Blazer + Maxi Slip Dress

Styling Notes: 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.

What You'll Need: Chunky Sandals + Printed Halter Dress

Styling Notes: 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.

High-Top Sneakers 

What You'll Need: High-Top Sneakers + Cotton Poplin Dress + Shoulder Bag

Styling Notes: 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.

What You'll Need: Leather Jacket + Knit Dress + High-Top Sneakers

Styling Notes: 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.

This post was originally published at an earlier date and has since been updated.