We Tested the ‘Wrong Shoe Theory’ and It Actually Worked...Kind Of

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Late this summer, I saw multiple TikTok posts and articles popping up talking about the Wrong Shoe Theory. The idea is that you can transform an outfit from simple (classic, basic, expected) to stand-out (cool, Fashion with a capital “F”) just by swapping your shoes from the “correct” shoe to one that feels wrong. In other words, choosing a shoe that is so unexpected it somehow goes all the way back around to feel right.

The Wrong Shoe Theory was first called out by stylist Allison Bornstein, who used a recent client experience to explain the difference between functional shoe choices and intentional shoe choices. In her example, she talks about a woman who wore a lot of sneakers for the very practical reason that she lives in a big city and is always walking where she needs to get to, but who felt that the sporty outfits she paired her sneakers with didn’t actually fit her personal style. Bornstein then asked her client to pull out three of her favorite outfits and purposefully pair them with a sneaker instead of whatever shoe she thought they should go with, and suddenly those looks felt much cooler and truer to her client’s personal style. “This is why I think the wrong shoe theory is so important,” she says in her post. “It sort of signals that there is some kind of intention and choice and therefore gives your look personality.”

Now, I love experimenting with fashion—trying weird color combinations, embracing trends that may not feel like me just to see how they work, etc.—so the idea that I may be able to get more use out of my shoe wardrobe without actually creating any new go-to outfits was incredibly appealing. That said, all I could think of when picturing how the Wrong Shoe Theory might work was a sea of ‘80s business women rocking skirt suits and running sneakers, which might make for a fun costume but is not particularly chic for 2023. I anticipated that I may find a limit to how and when this theory actually works. Turns out, I was right. Read on for my findings and a proposed twist on the Wrong Shoe Theory to make this styling trick even easier to implement.

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wrong shoe theory sundress
Abby Hepworth

1. Boho Mini Dress

Right Shoe: Dainty Flats
Wrong Shoe: Combat Boots

I started things off easy with a flirty, patterned sundress that I would typically pair with pointy-toe flats or a sleek strappy sandal, but instead opted to wear with some tough moto boots. I’ll admit, this is a combination I’ve tried before, and have seen numerous others pull off with aplomb, so it didn’t feel like too much of a stretch for me. I like the dichotomy between a preppy or boho frock and a tough, practical boot (I suspect a hiking boot may also look very cool) and feel this would work with just about any variation of the two. All in all, I was off to a good start.

wrong shoe theory sweater dress
Abby Hepworth

2. Knit Midi Dress

Right Shoe: Slim-Fit Boot or Heel
Wrong Shoe: Sporty Sneakers

Next I pulled out a newer fall favorite, a pleated knit maxi dress from DISSH. I usually amp up the posh vibes of this quiet luxury-inspired piece by wearing it with gold statement jewelry and a sexy, pointy-toe boot or heel. On the opposite side of the spectrum lies comfortable, everyday kicks—with a tall sock, no less—so on they went. This was a look I feared would veer into ‘80s business woman vibes, but actually looked cooler than I anticipated. The casual sneaker made the dress feel more low-key, like something I could wear just for hanging out with friends as opposed to only at the office or out for dinner.

wrong shoe theory denim midi
Abby Hepworth

3. Denim Midi Skirt

Right Shoe: Knee-High Boots
Wrong Shoe: Running Sneakers

With two successes under my belt I felt it was high time I dove head first into my ‘80s-coded fears and wore the 2023 version of the working woman’s office ensemble: a matching denim skirt-set and a neon-hued running sneaker. Typically, I’ve advise pairing a denim midi with a sleek knee-high boot to avoid looking bogged down by that much denim. These silver Renaissance Tour-inspired boots added yet another dose of cool, but you could just as easily opt for a classic black or brown pair. Slipping on my high-tech HOKA racing shoes certainly felt wrong, but I have to admit, it wasn’t nearly as cringe as I’d feared. The vivid colors (complemented by a bright pink sock) popped in a way that a more subdued white or gray pair would not, and therefore looked more like a fun accessory than a podiatrist-recommended support shoe. I ultimately didn’t love this combo enough to consider working it into my regular rotation, but liked it far more than expected, which still counts as a win in my book.

wrong shoe theory suit
Abby Hepworth

4. Office-Ready Suit

Right Shoe: Classic Pumps or Pointy-Toe Flats
Wrong Shoe: Chunky Sandals

Last, but not least I wanted to try a combination that felt truly “wrong.” In this case that meant wearing a tailored suit with my tattered, outdoorsy, waterproof Teva sandals. This was perhaps the most pleasant surprise of the bunch and I was shocked how much I liked the look of my pleated trousers with a chunky, adventure-ready sandal. I also tried on an even dorkier hiking sandal/water shoe in a splash of bright colors a few days later and loved them as well. Whereas my pointy-toe slingbacks made me feel polished and put together, like I would be instantly approved for a loan at the bank, the chunky sandals made me feel fashion-forward and cool, like my fellow fashion editor friends might compliment my look and ask for deets.


Bornstein is right that trying an “opposites attract” approach to choosing footwear does yield some surprisingly cool results that ultimately made my outfits feel more intentional and more like a personal style choice. But I think there are limits to how “out there” you can go with your shoes and still look intentional. In general, I found swapping a fashionable shoe for a more practical one—boots for sneakers or pumps for sandals—ended up looking way cooler than going in the opposite direction. Replacing simple Keds with a sky-high stiletto heel felt far too mismatched when wearing loose denim, as did wearing cowboy boots with a suit trouser. If you want to test out the Wrong Shoe Theory for yourself, I advise thinking of it more as the Practical Shoe Theory, wherein you replace the “correct” fashion-forward shoe with one that’s infinitely more practical or comfortable.

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Abby Hepworth


Abby Hepworth is an RRCA-certified running coach who has worked in fashion for over 10 years. Want to know what shoes are in this season? She's got you. Need recommendations on...
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