What Do I Wear With My New Ugly Sneakers?

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If you’re a sentient being who reads the Style section or even just looks down occasionally while walking, you’ll have noticed that we’re living in the Era of the Ugly Shoe. If this is news to you: go outside. Look downward. See the feet ensconced in bulky, colorful, dad-ish sneakers. Those are horrible, you might think. Then, probably: Where can I get a pair?  

Though procuring a pair of affordable Ugly Sneakers™ may seem simple enough — Foot Lockers are rife with unattractive running shoes, after all — finding a pair that read as cooly ironic rather than horribly sincere is not easy.

My hunt for a pair of Ugly Sneakers began a couple weeks ago — long after every fashionable person I know had already worn in their chunky New Balances or color-blocked Balenciagas. I didn’t know which to buy, so I reached out to my stylish friend Nora, a copywriter who bought her pair of appealingly alien-looking Nike Air Maxes some seven months before they became popular (she did the same with mules, wide-legged pants, and the color orange). She suggested I try some all-black, deeply orthopedic-looking black Air Force 1s, and since it was a Saturday and I’m a lemming I hoofed it straight to the Nike store and bought them on the spot.

I may have won the battle (finding and procuring ugly shoes), but as it turns out, I had not won the war. Each time I tried to wear the Ugly Sneakers out of the house I was stopped by my mirror — they just didn’t look right. So back they went to my shoe stand, where they took up two spots. I quickly deduced that the problem was that the sneakers looked terrible with many of my pants: my white Rachel Comeys, my wool checkered trousers. I decided to call back Nora to see if she could help. And readers, Nora is the best kind of friend: she came over to my house and taught me how to style the flummoxing shoes. Her advice was so utterly helpful that it felt unfair to keep it to myself. Fortunately, I have a platform for such useful-slash-absolutely-pointless lessons: The Strategist. Enjoy.

For shoes with a pointier toe and straight sole …

Air Max 97 Ultra ‘17 SE Sneaker

These are Nora’s Ugly Sneakers. They pair well, she says, with straight legged, slightly flared, ankle-bearing pants. Do not attempt to wear them (or any other ugly sneaker), she says, with overtly ’70s-ish pants. A subtle kick flare is fine, but make sure it stops at the ankle.

Hoka One One Bondi 5

Yikes: These Hokas are incredibly ugly, but have a similar vibe to Nora’s Air Maxes.

Wear straight-leg and cropped black pants

NEED Ever Pin Pant

These are pants that you could wear nicely with your Nora Sneakers, as I now call the very popular Nike Air Max. They are also plain enough that they would both highlight and offset the ugliness of the Hokas.

For heavier shoes …

Nike Air Force 1 07

These are my Ugly Sneakers! I love them.

Wear ankle-baring pants or jeans

Rolla’s Miller Skinny Jeans

Nora told me to wear them with my cropped vintage Levi’s. These jeans, she says, would also look great with them because they are cropped at the ankle (if your pants bag into your Ugly Sneakers, she warned me, all coolness is lost — and you are just a person wearing ugly sneakers.)

The Wide Leg Crop Utility Pant

Nora also recommended I wear them with my brown wide-legged Rachel Comey pants, which look a lot like these, but are only $68.

For a funky, jagged-soled sneaker …

Marni Paneled Low-Top Sneakers

These sandal-like shoes are on Nora’s wishlist right now.

Fila Disruptor II

These on-trend white sneakers are very affordable.

Wear cropped and slim white pants

AG The Rhett High Waisted Jeans

These, which were top on the list of our Best White Jeans for Women list, would be a nice option. Nora suggests white, cropped pants with sneakers like these because they’re fitted enough to offset the bulkiness of the Fila.

For slim-profile ugly sneakers

Nike Air Vapormax Flyknit

These Nikes are narrower than the Air Force 1s, which will make them far easier to style. But don’t worry: The cleats on the bottom make them plenty ugly. Plus you can run in them!

Wear high-waisted and wide-legged pants

Creatures of Comfort Maison Pant in Conductor Stripe

Actually, any all-black ugly shoe would look great with these striped trousers.

And what socks?

Carhartt WIP C-Logo Socks in Glacier

Here’s a final lesson from Nora: When wearing the Ugly Sneaker, choosing the right sock is very important. Cropped socks and mid-length socks are good, she says. Patterned socks are great with a solid-colored Ugly Shoe, but, she warns, don’t get too “Happy Socks-ish.” Try a solid color, a simple polka dot or stripe, or a plain color with a pattern. I picked these blue socks on my own, and I hope she’s proud.

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What Do I Wear With My New Ugly Sneakers?