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How Do I Quit My Skinny Jeans?

The time comes in every relationship when you just need a little more room to breathe

About a decade ago, a newly minted working man took to the subreddit r/MaleFashionAdvice (MFA) looking for suggestions on how to break up with his skinny jeans. “They’ve been with me ever since my dirty skateboarder days,” he explained. “But nowadays, I’m a contractor where I meet with a wide range of people. So I need to steer away from looking like a kid.”

To which another redditor humorously responded, “First, sit your skinny jeans down somewhere where you two can talk alone. Explain that you’re looking for a wider, looser fit and how having them around makes you feel inadequate and restricted. It’s important that you let your skinny jeans know that even though things between you two are still comfortable and feel right, in the end you need a change. Don’t bring up any of the stories of you trying on the bootcut or relaxed fit, it will only make things worse.”

“If you’re lucky, maybe you two can work things out rationally where you can still wear each other from time to time,” he continued. “After all, this isn’t goodbye, it’s just business. There will be plenty of opportunities out of work where the two of you can still hang out together.”

It’s both funny and all too real for me. I also used to only wear skinny jeans. And I also struggled to let them go. My come-to-Jesus-in-black-Ksubis moment arrived a few years back when I looked in the mirror as I was getting ready for a date and realized, “You look… uncomfortable.” 

I subsequently tried on regular-fit pants, bootcut jeans and wide-legged trousers, but none of them ever felt right. I’m short and skinny, so it’s very easy for a pair of non-skinny bottoms to turn my legs into two sticks surrounded by a couple of hot-air balloons. 

Ever since, it’s been a bit of a process. But that’s also exactly what all of the MFA superusers endorse — a course of gradual change. Case in point: One such superuser was in my exact same position and slowly used “tapered fits” to get out from under the shadow of his skinny boys. (Tapered fits more or less have the same small leg opening as skinny jeans, which is typically among what people — read: me — like best about them.) He suggests starting with a pair of Levi’s 514 before going for the slightly looser but more classic 501s

Even more specifically, another frequent MFA poster recommends the following: “Figure out the leg opening on your current pants (my guess for skinny jeans is around 13 inches). Now, find some pants that are a bit wider, maybe a 14-inch leg opening. See how you like it. Maybe that’s wide enough for you. Maybe you want to explore more. If so, look for a 15-inch leg opening.” He says the circumference of the leg opening is a good measurement to go by since it’s usually available from even mall brands like J.Crew and Banana Republic. “Except for athletic-taper/relaxed-tapered pants, it gives you a pretty good idea of how the rest of the pants will fit,” he adds.

Another measurement to consider is the length of pants you’re transitioning to. “I’d start with zero or a quarter break,” a third MFA poster tells me. “That way you won’t have so much material bunched up around your shoes.” Which again, helps mitigate the feeling that you’re wearing hot-air balloons around your legs. 

Or in breakup terms, makes it feel as though the one you’ve parted from isn’t so far away after all. 

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