Toby Melville / Reuters

It’s not that I think wearing Toms with socks to work is a good look, per se.

I admire your d’Orsay oxfords and fun mules. But unfortunately, when it comes to shoes, my only criteria is “Will these cause my feet to dribble blood all over my open-plan office?”

I am simply not meant to wear professional office flats. I can’t wear Payless flats, but I also can’t wear the premium, handcrafted-in-Italy, join-the-wait-list flats. I don’t even attempt heels. No matter what brand they are, what width or size, any shoes that you can’t play basketball in will, inevitably, rub Medieval-looking holes into my foot skin.

Every month, I succumb to an Instagram advertisement or a Strategist post purporting to have found the holy grail of women’s footwear: comfortable and work-appropriate. Reluctantly, my shoe-price ceiling has risen with the number of subcutaneous infections brewing on my heels. I buy them with a renewed sense of hope every time. Every time, I eagerly unwrap the shoes, slide them on in my carpeted apartment, and note how comfortable they feel—You get what you pay for, I think smugly.

Then I hit the streets, where it all goes wrong. The unyielding little back digs itself into the area right below my Achilles tendon, then shreds it with every step. And so every time, I send boxes of bloody shoes back in the mail like a serial killer. (I will say that you do get the return policies you pay for.)

I always thought this was just part of being female. You wake up, you apply powders to your face to make parts of it different colors, you walk to work, your feet bleed. There is simply no way to look as professional in a shift dress and Allbirds as you can in a fleece vest and Allbirds. Beauty is pain, I figured, and so is professionalism.

More women than men suffer pain from their footwear, according to podiatric surveys, and similarly, more women than men say they’ll suffer for the sake of their shoes. A few years ago, there were stories of, ahem, well-heeled women getting “pinky tucks” and toe-shortening surgery so their feet could fit their shoes, rather than the other way around.

Studies reveal the excruciating outcomes of this disparity: “In women ... those who wore good shoes in the past were 67 percent less likely to report hind-foot pain, after adjusting for age and weight,” one big study from 2009 notes. “In men,” the authors added, “there was no association between foot pain, at any location, and shoewear,” possibly because fewer than 2 percent of men in the study wore “bad” shoes.

My own bad-shoe wearing peaked in college. My friends and I would walk home from bars so wracked by agony that we would take our shoes off and walk on the freezing, filthy cement. Only recently, when I was in so much pain after work that I seriously considered reliving my college days—walking down the Metro escalator barefoot and carrying a pair of blood-splattered loafers—did I decide to take this problem to a couple of podiatrists.

The foot doctors, first, validated my feelings. “Women’s shoes are tighter; they’re meant to fit tighter around the toes and the heel,” Cary Zinkin, a spokesman for the American Podiatric Medical Association, told me. “They’re made to make your foot look as slim as possible.”

But Marlene Reid, a podiatric physician in Naperville, Illinois, told me “it’s not normal” to be julienned by your own footwear, as I am on a regular basis. I was surprised to learn that you shouldn’t have to “break in” shoes. They should not be painful the first few days you wear them. “If you try on a shoe that hurts from the outset, don’t buy it,” Zinkin said.

All feet are different, and so are all shoe sizes. Any shoe that’s too loose or too tight can cause a blister, Zinkin said, and a lot of friction can actually rub away the skin, which appears to be what’s happening to me.

My feet don’t look like any of the feet that show up in a Google-Image search for this, but Reid suspected that I might have what’s called a “pump bump,” a bony growth on the back of the heel that makes it hard to wear pumps—and other kinds of dressy shoes, apparently. She suggested that I try “heel lifts,” little insertable wedges that might hoist my bump out of harm’s way.

Both Reid and Zinkin recommended that I use moleskin, gel pads, or even lubricants—like the body glide that athletes use to keep their nipples from chafing—to help me tolerate any shoes I just can’t bear to part with. Zinkin told me that skin tends to be more blister-prone if it’s dry, so I guess I could also try to lotion up my heels, as though I’m preparing to make a coat of my own skin.

One reason so many women are injured by their shoes these days might be the rise of online shopping—you don’t know how the shoe fits until you’ve already bought it. Instead, you’re supposed to shop in the store, preferably in the afternoon, after your feet have swollen to their fullest. When you shop, you’re also supposed to bring along whatever tights you wear, plus any gel pads or heel lifts you use, and stick the whole contraption inside the shoe when you try it on. Also, most shoe stores are carpeted, Reid said, so you want to walk to an area of the store that has tile or wood.

If you bring the shoes home and they’re still too tight, take them to a shoemaker to stretch them. (Just keep in mind that natural fabrics like leather stretch more than synthetics.) Reid debunked the common notion that flats are always better for you than heels. “Some of the flats that have been out there are really hard and don’t stretch,” Reid said. “They’re rigid. I’d rather someone wear a heel that they can tolerate than wear a flat.” She recommended the Fly London brand as a good mix of comfortable and acceptable for work, and while they look a little too ’90s punk for me, to each her own.

Reid also told me something that I didn’t want to hear: Ultimately, I’d have to spend even more money on an already-expensive problem. “If you have the same recurring problem with multiple pairs of shoes, see your podiatrist,” she said. “They will show you how to wear shoes that work with your feet.”

Something tells me their answer is gonna be Toms—preferably with socks.

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