Arbitrary fashion rules have caused us to set boundaries on how we dress (does the strange tradition of not being allowed to wear white shoes after Labor Day confuse anybody else?). But nowadays, people feel more empowered to wear what they want, when they want, thanks to pandemic dressing and the rise of maximalist fashion. Because of this, so-called fashion “rules” are becoming defunct. Even Coco Chanel’s famous suggestion to take one thing off before leaving the house is laughable to dopamine dressers.

The best ‘wrong shoes’ at a glance:

• Klaw, 528 Walking Shoes, $148
• Asics, Gel-Resolution 9 Tennis Shoe, $120
• Crocs, Classic Clog, $37
• Hoka, Gaviota 5, $175
• Wörishofer, Women’s 251 Sandal, $79
• Tecovas, The Abby, $335
• Vionic, Minna Ballet Flats, $120

Take shoes, for instance. Back in May, stylist Allison Bornstein shared on TikTok her idea of the “Wrong Shoe Theory,” which is essentially pairing clothing with a non-traditional shoe, say a dress with sneakers, making the entire outfit look more personal and exciting. In the video, Bornstein goes on to describe how she helped a mom client style her favorite pieces with the same pair of sneakers, resulting in the shoes looking like an “intentional styling decision.” Not only did the sneakers serve a functional purpose, but the overall look felt more authentic to the client’s personal taste.

What stylists say

Of course, wearing an unexpected shoe with an outfit isn’t anything revolutionary. Kristen Stewart famously paired Converse Chuck Taylors or Nikes with designer dresses for years, her reason being that she could comfortably sign autographs for Twilight fans. Just this past May, Jennifer Lawrence swapped her stilettos for plain flip-flops at the Cannes Film Festival. And who could forget that iconic moment in 2017 when Rihanna paired white sneakers with a blue tulle Molly Goddard gown? Still, thinking of it as a way to style with intention is revolutionary in itself.

But do other stylists agree with the Wrong Shoe Theory? Stylist Gabriela Rosales says that it depends on how the entire ensemble looks overall. “I do believe that personal style and impactful aesthetic do not have to come at the cost of comfort (and that’s coming from a Taurus),” she says. “I also believe that anything can be styled in a way that is harmonious and aesthetically pleasing so generally speaking, yes, I am pro-ugly shoe.” When it comes to Crocs or orthopedic clogs, Rosales prefers them with pants over dresses. “Shoes like Hokas and Klaw sneakers pair well with sun dresses, mini dresses, or mini skirts, and can add a bit of a street style flair when paired with them,” she says.

Celebrity stylist and owner of the rental house Clothed LA, Jordan Grossman, says that sneakers and dresses always look great together, but sees Crocs as more versatile. “I think you can style Crocs with anything, really, because they’re already so ugly, they’re kind of cute,” she says. “Obviously not with an evening gown,” she adds, “but like any day dress, any shorts, will look cute with them.”

What podiatrists say

When it comes down to it, wearing comfortable, well-fitting sneakers is a good idea, especially when you consider the risks of other shoes like high heels. Nelya Lobkova, DPM, a surgical podiatrist, the founder of Step Up Footcare, and biomechanics consultant for the footwear brand Klaw, points to a myriad of possible risks for high heels and platform sandals, including stress fractures, lower back pain, bunions, hammer toes, and Achilles tendonitis.

When shopping for a good orthopedic shoe, Dr. Lobkova says to look for a firm heel counter, a cushioned midsole, a round and deep toe box area, arch support, a rubber outsole, and simply making sure that the shoe fits comfortably, not too tight or too loose. For sneakers, Dr. Lobkova says that there’s a delicate balance to finding the optimal casual style. ”Casual sneakers should be more rigid (less flexible) and heavier than an optimal running sneaker, but at the same time more supportive and stable than a lifting/training shoe.”

Ready to test the Wrong Shoe Theory for yourself? Ahead, see seven of our favorite picks with tips on how to style them.

7 ‘wrong shoes’ that are right for every outfit

Klaw, 528 Walking Sneaker — $148.00

Available sizes: women’s 6-11 in half sizes and two widths

These Klaw sneakers have everything you need in terms of support and comfort, including incredible arch support, a light and cushioned midsole, and a deep heel cup for stability. Plus, they’re made with soft rainproof leather that comes in white, yellow, gray, and black. Do what Rosales suggests and pair them with a cute mini dress; a pleated skirt and a crop top or t-shirt would be a super cute look.

Read our full review here. 

Colors: 4

Asics, Gel-Resolution 9 Tennis Shoe — $150.00

Available sizes: women’s 5-12, in half sizes

These tennis shoes totally ace any outfit. Made for the court, the Gel-Resolution 9s take stability and cushion to the next level. Using Dynawall technology, the midsoles are ultra-stabilized for side-to-side movements, while gel technology in the rear- and forefoot takes care of impact absorption. Take them off the court with jeans or a dress for a look that “serves”.

Colors: 5

Crocs, Classic Clog — $37.00

Available sizes: women’s 6-12

Shorts, trousers, dresses, skirts, a bathing suit—there’s really no wrong way to rock Crocs. Arguably the original “wrong shoe” the Crocs Classic Clog has been a mainstay in wardrobes thanks to its comfort, versatility, and ugly-cuteness. Go wild and accessorize the upper and backstrap with all of the Jibbitz charms you can handle, then wear them with any dress or pants in your closet that inspire you. 

Colors: 27

Hoka, Gaviota 5 — $175.00

Available sizes: women’s 5-12, in half sizes and two widths

The Gaviota features super soft foam midsoles and a unique, H-Frame base for total stability. While they’re technically road-running sneakers, you’ll be comfortable wearing these chunky shoes to walk the dog, run errands, and more. Pair with a maxi skirt for a “wrong look” that’s totally right. 

Colors: 5

Wörishofer, Women's 251 Sandals — $79.00

Available sizes: EU 27-41

These granny sandals were big with fashion insiders in the mid and late 2000s, but Lily Depp was spotted in them this summer, so they’re prime for a comeback. She wears them with everything from jeans, shorts, and dresses, but try pairing them with your favorite chinos for a different take on Coastal Grandma.

Colors: 9

Tecovas, The Abby — $335.00

Available sizes: women’s 5-12, in half sizes

These days, you can’t scroll through TikTok without seeing a pair of cowgirl boots paired with a dress or denim cut-offs. It’s such a cute look, and proves that western boots look good well beyond the ranch. Take the Abbys, which are Tecovas’ tallest western boots to date. Complete with a 17-inch leather shaft and a 2-inch heel, they instantly elevate any outfit (literally and figuratively.)

Colors: 3

Vionic, Minna Ballet Flats — $120.00

Available sizes: women’s 5-12, in half sizes and three widths

Ballet flats have been back in fashion for a minute. While these are much more versatile compared to the other shoes on this list, you can still shake them up in terms of styling. One way to do that is to pair them with oversized jeans or wide-leg pants instead of a skinnier silhouette. 

Colors: 6