Wearing Sneakers With Dresses Is A Distasteful Walk Toward The Dark Side

After months of wearing tired, salt-stained boots, stepping into our favorite spring and summer styles can feel exhilarating. Some warm-weather outfit pairings are simply timeless, like denim shorts and trainers or minidresses with gladiator sandals. Such looks may not be for everyone, but there's no denying their lasting appeal to fashion-savvy consumers throughout the decades. Still, there's one persistent styling phenomenon that we'd argue manages to miss the mark entirely: sneakers and dresses, or S.A.D.

Year after year, the dreadful intersection of athleisure and casual dress makes its way across American cities as temperatures rise. It's hard to pinpoint the exact origins of this unlikely combination, but it appears to have risen to prevalence during the 1980s and has held on tight ever since. Like a grisly scene in a nature documentary, S.A.D. may captivate attention — but for all the wrong reasons.

Getting dressed to the nines just to run errands may be a thing of the past, but swapping your footwear for something more flattering is effortless. Hear us out: sneakers worn with dresses are the warm weather equivalent of throwing a coat over a lackluster outfit and calling it a day. With myriad styling options at hand during the sunnier seasons, it's impossibly easy to take your fit from underwhelming to unbelievable. Best of all, it can be done without ever sacrificing your comfort. Want to know more? Ahead, we'll explain why sneakers with dresses often fall short, and how to avoid this common summer fashion mistake.

The look is bad enough with some sneakers but worse with others

Casual, low-top sneakers are the most common offenders when it comes to this questionable look. However, they're not quite as egregious as others. Certain styles, like chunky-soled running sneakers, are near-impossible to pair with dresses without appearing dowdy. The biggest qualm we have with sneakers and dresses is the unsightly silhouette. More often than not, a drab final look results when a casual, rumpled sundress is accompanied by bulky shoes. Let's put it this way: if your high school gym teacher would wholeheartedly approve of your sneaker selection, it's probably not the best match for any type of dress.

But what about other types of sneakers? Well, it's complicated. Some dresses, like bodycon jersey designs, get a pass when worn with classic basketball shoes, but are one of the few exceptions to the rule. If your aesthetic is pure '80s vixen, replete with Reebok Freestyle high-tops, you might be able to pull things off, as Cybill Shepherd did at the 1985 Emmys. That said, the 'shabby-chic' juxtaposition of modern trainers against floaty day dresses is a more accurate representation of how the S.A.D. look is typically styled. Sure, this carefree ensemble is appropriate playground gear for school-age children — but it falls flat by fashion standards. Even Ms. Frizzle, the unforgettably-dressed protagonist of "The Magic School Bus," sensibly opted for tasteful heels over tennis shoes despite her wild style predilections.

If you're going to go grunge, go all the way

Sneakers with dresses are often described as comfy chic, unpretentious, or similar phrasing that hints at their 'cool girl' spirit. But let's face it — much of their appeal comes from choosing convenience and comfort over style conventions. And in many ways, that is admirable. Still, the combination leaves something to be desired in terms of overall appearance. Sneakers are essentially interchangeable from the worn flip-flops you gravitate toward all summer because they happen to be closest to the doorway.

Think about some of your most memorable outfits. True, it's possible to strike gold from time to time while dressing in a rush. Sometimes fashion risks pay off, and potential hit-or-misses can be endless compliment magnets. But generally speaking, a great 'fit requires at least a few thoughtful touches to tie things together. Wearing sneakers with dresses seldom conveys thoughtfulness — instead, it serves chaotic laziness, like smashing your snooze button and fumbling for the few remaining pieces of clean laundry.

At their core, sneakers and dresses are a match made in hell: puzzling, incongruous, a vulgar gesture aimed directly in the face of fashion itself. But if their defiant message resonates with you, or you're truly confident you can style sneakers with dresses in an intentionally disheveled way, have at them. Otherwise, this discordant duo leans toward sloppy and unkempt, an unfortunate outcome when styled under pretenses of chicness.

Comfortable footwear alternatives you could wear instead

Luckily, there are still ways to sport sneakers and dresses with minimal offensiveness. If you want to elevate your sense of style, we'd strongly suggest you consider some sleeker footwear choices alongside your flowing hems. Athletic flats, orthopedic sandals, and even hybrid sneaker designs are vast improvements over traditional trainers if you're determined to rock dresses with sneakers. For example, try slipping into trimmed-down flats, like Keds Mini Eyelit Slip On Sneaker, instead of clunky jogging shoes.

Monochromatic color schemes are another way to add a touch of sophistication to ordinarily gauche sneaker and dress pairings. Explore sharper styles, like a black babydoll dress with matching platform sneakers or neutral slip and skimmer sneakers in coordinating hues. Just remember, crisp, canvas low-tops, like classic Converse, are the most inoffensive option for a sneakers-and-dress combo. Your hulking, mud-stained marathon sneakers, on the other hand, are best saved for the gym.

Ultimately, don't let this advice sway you if you're dressing for comfort or have a medical concern. After all, no one should suggest you compromise your health or sense of well-being for the sake of fashion. If nothing soothes your soul like a pair of New Balances beneath a beach dress, don't let us step on your toes. Summer fashion should be fun, comfortable, and, most importantly, reflect your tastes. We may disagree with sneakers worn with dresses, but if they suit your style, feel free to run with this fashion faux pas.