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How Much Discomfort Should I Put Up with Because Something Looks Good on Me?

These shoes are squeezing the life out of my feet, but goddamn, if they don’t look amazing

I often wear my pants just at or above my belly button. Not because I’m ashamed of my navel. But because I prefer the style of a snatched waist. As my colleague Magdalene Taylor has written, snatched waists are “audacious and bold.”

The thing is, it’s not super comfortable. Actually, it’s not comfortable at all, placing consistent, noticeable pressure on my gut. But that’s the trade-off — pain in the interest of audacity and boldness.

Now, women have suffered forever in the name style and meeting an era’s requisite beauty standards (see, at a bare minimum: high heels and corsets), but at what point is that suffering too much?  

Interestingly, there’s some research that suggests that wearing clothes that are too comfortable runs counter to having a good day. The concept is referred to as “role theory,” and according to a report in the Huffington Post, it means that dressing in sweatpants when you’re already having an off day could send you spiraling further. Which makes sense — in that, dress for the job you want, not for the job you have, sort of way. “I wear a suit and tie every day,” one menswear blogger tells me. “I’m not going to lie to you and say that it’s the most comfortable wardrobe, but I feel really good in it, so I forget about the discomfort.”

Pain can be relative, too. Case in point: I recently wrote about a bunch of guys who wore jeans as thick as fire hoses every day for a year all in the name of attaining the sickest fades. They were willing to trade bloody thighs and the total removal of leg hair for the looks they wanted to achieve.

All of this, of course, flies in the face of our current moment. Namely, in these COVID times, most of us work from home, where no one but our partners or roommates typically see us. So why bother wearing stiff leather shoes or an itchy wool shirt when you can wear comfy athleisure instead? 

Again, the answer is a completely emotional one. The only logic being that it might physically make us feel bad, but mentally, it makes us feel great. Or as one denizen of the MaleFashionAdvice subreddit puts it to me bluntly, “I don’t like being uncomfortable. But I also don’t like wearing sweats.” He adds that a compliment from a friend or colleague on the pattern of his tie or the shape of his leather boots makes the discomfort completely “worth it.”

As they say, no pain, no gain.