Why Do Men Keep Their Shirts on During Sex?

An investigation into a sartorial choice that leaves some men looking like a horny Winnie the Pooh

October 21, 2021 5:30 am
Black and white photo of a man wearing a red shirt and no pants with his hands clasped over his crotch
The full Winnie
drbimages, Erik Von Weber

I have a few questions for men who keep their shirts on during sex, namely: Why? 

As a woman who refused to remove her bra during sex for the first four years of my sex-having career because I was afraid my tits were weird, I don’t really have any business questioning anyone else’s choice to keep an article of clothing on during the act. But as a sex writer — or, as Carrie Bradshaw once embarrassingly put it, “sort of a sexual anthropologist” — it’s kind of my job. So let’s move on with this friendly interrogation, shall we?

This is a phenomenon that I’ve noticed occasionally and randomly, with no obvious pattern or reason. When it comes time to strip down for sex, some men start from the waist down, simply freeing the necessary equipment but remaining clothed north of the genitals. While I suppose this is an efficient way of disrobing for the task at hand, I tend to find it a little confusing, and, frankly, kind of unsexy. As the internet rarely tires of pointing out, the shirt on, no pants look is straight out of the Hundred Acre Wood. 

While women may have a slightly easier time pulling off waist-down nudity, (think the ubiquitous if largely fictional “woman wearing a man’s work shirt after sex” trope) a man standing there with a hard dick poking out from underneath his shirt hem just looks like a perverted Winnie the Pooh. Moreover, in keeping your shirt on during sex, you are robbing both yourself and your partner of precious skin-to-skin contact, which can enhance sexual intimacy and pleasure, as well as the opportunity for proper back scratching. 

Of course, as many people I’ve talked to while working on this piece have pointed out, some men who prefer to keep their shirts on during sex are probably insecure about their bodies. Again, as a woman who kept her bra on during sex like a teen in a cable TV show for nearly half a decade, I am sympathetic to the plight of the bodily insecure and/or dysmorphic. Whether it’s unwanted extra weight, perceived lack of muscle tone, too much or too little hair or a skin condition, I can understand why certain men dealing with a physical insecurity may be reluctant to dispense with the comforting veil of a T-shirt. 

However, like a chubby kid who keeps his shirt on in the swimming pool, you’re not actually hiding anything. If anything, keeping a shirt on in situations in which one would typically be expected to take it off is a dead giveaway that you do, in fact, feel insecure. And the only thing worse than being insecure about the thing you’re insecure about is people knowing you’re insecure. Of course, everyone has a right to assert and maintain boundaries about their bodies, especially when sex is involved. Still, if you want my advice, it’s better to just take it off. Anyone you’re having sex with should accept and respect your body, perceived flaws and all. 

That said, it’s not really insecure men that I’m confused about. It’s the ones who keep their shirts on without any obvious source or sign of insecurity, especially when it’s done inconsistently. Kaitlyn, a pseudonymous 20-something in Boston, says the man in her life keeps his shirt on “not exclusively, but approaching half the time.” This inconsistency, she adds, “is even more confusing.”

Moreover, she’s “fairly confident it’s not a self-confidence thing,” and for good reason. Outside the bedroom, she says, “my partner is shirtless a lot of the time.” It also doesn’t hurt that he happens to be “embarrassingly, arrestingly attractive, and lowkey knows it.” To summarize: “Yeah, he’s not insecure about his body at all.”

When probed about his occasional shirt-on, pants-off approach to sex, Kaitlyn’s partner usually delivers what she considers to be a “pretty goddamn charming” response: “Usually I’m just too eager to pay attention to you.”

Still, Kaitlyn says she’s been forced to demand the shirt come off on two circumstances due to disturbing or otherwise distracting graphics on said shirts, including images of “a cat in a Bill Cosby sweater” and “Rowdy Roddy Piper’s face.”

Meanwhile, the unself-conscious, occasional shirt-wearing sex partner in my own life — AKA this article’s unwilling muse — mounts a similar defense. 

“It’s not an insecurity thing,” says the anonymous source I have chosen to call Salvatore, though he does add that “it may be” for some men. “It’s really sometimes you’re just caught up in the moment. It’s not intentional. It’s not like you go into it saying, ‘I gotta keep this on. Shirt’s gotta stay on.’”

Room temperature also has to do with it. In a cold room, Salvatore says it makes more sense to keep a shirt on, only removing it when and if things heat up, both literally and figuratively. “If you’re in the heat of the moment and it’s cold — in the room, in the car, wherever — you’d rather not stop the momentum [to get under the covers]. You don’t want to ruin the mood.” 

Personally, I don’t think briefly hitting pause to get under the covers and resume sex beneath the comfort of some warm blankets “ruins the mood” any more than keeping your shirt on, but okay. Anyway, Salvatore would also like me to note that it’s not like he’s “wearing some gross, disgusting shirt,” — or, say, one with a Canadian wrestler’s face on it — but rather, “a sexy white shirt,” through which, he insists, “you can almost see [his] abs.”

Meanwhile, as others have pointed out, in movies a man’s partner usually removes his shirt within seconds of largely non-existent onscreen foreplay. So perhaps I have simply been remiss in my own pre-coital shirt disrobing duties.

Regardless, it feels important to note once again that everyone is of course well within their right to assert their own sexual boundaries. If, for you, that means keeping your shirt on, go right ahead and Winnie the Pooh that shit. Just know that no matter how sexy your white shirt, you look a little silly with your Hundred Acre Wood poking out under it.

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