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.
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.
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.
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.
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.
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.
Make your favorite black dress transition into the daytime by wearing it with a button-down, knee-high socks, and loafers.
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.
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 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.
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.
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.
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.
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.
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.
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.
Want to lean into the Western aesthetic fully? Try pairing cowboy boots with a vintage-looking lace dress and shoulder bag.
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.
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 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.
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.
Looking for a way to dress up the flat strappy sandals in your closet? Try pairing them with a minidress and blazer.
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.
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.
You also can achieve the “preppy” look by styling an oversize button-down with an oversize sweater-vest and oxfords.
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.
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.
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.
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.
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.
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.
