I've Never Met an Ugly Shoe I Didn't Love

It's my small, subtle act of rebellion.

I remember when I decided to stop wearing heels to work. I was working at Seventeen, feeling busier than ever, with my longest commute (the Clinton-Washington G train to the A at Hoyt-Schermerhorn to 59th St. and a walk to the Hearst Tower), plus a packed schedule. Do you remember when we did a 7 a.m. spin class, went to DryBar, worked all day in the office, and went to at least one nighttime event? Yeah, I don’t know how I did it either. I do know it wasn’t in heels.

My first editorial job was at Time Out New York, where jeans, band tees, and Converse sneakers were the uniform. But when I started at Hearst, I realized people got way more dressed up. I had the clothes but had to get a few pairs of pumps and ankle boots (hey — it was the 2010s) to look the part. It was fine for a while. But one day, after I ordered lunch delivery to my desk, I realized my new shoes were making me lazy. I used to love going for walks to find food. I rarely took cabs. Wearing heels was keeping me from doing things — and making me feel strangely helpless. What if someone sketchy started following me on the train? Could I run in these platforms?

That started my love affair with “ugly,” shoes and it’s only gotten worse (better?).

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Right now, I’m in a sneaker phase. so it could be mixed laces (like the Miu Mius above) or an animal print or bright color. Last year, I got into funky ballet flats (like buckles and mesh and studs), and the year before, I wore cowboy boots with basically everything. It’s a mix of wanting to feel free (and not stuck calling an Uber because my feet hurt) and what stylist Allison Bornstein calls the “wrong shoe theory.” To keep an outfit from looking too put-together, too precious, an unexpected shoe is usually the perfect finishing touch. Try it — it works every time.

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I’ve been thinking about what my ugly shoe obsession is going to be this year, and I think I’ve finally found my answer. I can’t get enough of sneaker-ified shoes, such as loafers and ballet flats with chunky soles and laces or tassels. These have that perfect mix of sporty and girly (I call it Sporty Spice) I think is very much my style. And since I’m carless in Los Angeles (some day, I will get my driver’s license), I’ll be able to pound the pavement while everyone else drives by me in their air conditioned cars.

Below are some styles I’m currently considering. I’ll probably end up pulling the plug on whichever ones actually have a size 5 in stock.

All products are selected by me. If you buy something, I may earn an affiliate commission.

Camper’s Karst shoe has everything I want: a chunky sole, a feminine Mary Jane style, and on-trend silver metallic details.

Hoka’s Speed Loafer is probably the most controversial, but I’m not the only one who loves them — they’re currently sold out and going for more than $700 on resale sites.

Cecilie Bahnsen’s Black Aria Sneakers are expensive but literally perfect. (The floral sole!) They’ll look so good with a Cecilie Bahnsen-style poofy dress and some frilly socks.

Not as chunky as I like but much more affordable, Steve Madden’s Scooter Sneaker might be the perfect in-between.

I love everything Salomon does, and its MM6 collab Mary Jane Colorblock Sneakers are extremely good. And very expensive.

JW PEI shoes are affordable and comfortable — but most styles don’t come in a size 5. (I hate my feet.) PLEASE, I need the Caitlin Lace-up Ballerina Sneakers with the pink laces.

Should I just give up and get Sketchers?!

Last year, New Balance released its controversial 1906 Loafer Sneaker in a perfect gray and silver colorway. They’re gone, and there’s no news when they’re coming back. But on March 19 at 10 a.m. EST, the 1906L in all black launches. I don’t love them as much as the silver, but I could be swayed.