Boxer Briefs: If you wear boxer briefs every day you most assuredly have given your underwear choice some quality thought. Typically, boxer brief wearers are the boys that made the transition from briefs to boxer shorts in middle school to “fit in” but as they hit puberty or gained more maturity and thus a heightened awareness of their body (and the need for support) they decide to split the difference around their junior or senior year of high school, or early on in college. It’s likely that their overall sense of style ranges from “if it fits and is comfortable, I’ll wear it” to “fashion-forward.” As one of the most popular styles out there today, it would be foolish of me to claim that the boxer brief reveals any universal personality traits or dispositions.

Trunks: If you’re wearing trunks, you had previously worn boxer briefs but tired of making a trip or two to the restroom to fix the legs that had ridden up throughout the day’s wear. Personally, I was never a boxer brief wearer, but had worn a couple of pairs to know about this universal problem, so I went straight to trunks. While I didn’t “stop” there, I was indicative of most men who do end up enjoying trunks enough to make it their preferred style. Trunk wearers are well-versed consumers because they have tried all of the “common” every day styles. The style itself accomplishes just about everything the trunk wearer likely wants in a pair of underwear: Support without having to go to a brief and the right amount of sex appeal without sacrificing (perceived) comfort. The trunk wearer is typically style-conscious, possesses a more athletic build, and wants to both look good in his underwear for his own self confidence, and for the people that might be seeing him in them. If I were to be liberal about what the trunk might universally reveal about its wearers, I’d say that they’re for men who, on outward appearance, convey an “Alpha Male” disposition (in the way they walk, talk, and handle themselves) but who might privately crave attention in a very contradicting self-conscious way.

Boxers: Men who wear boxers naturally come to be perceived as “laid back” because the style allows your package to hang free. Personally, I think the majority of men who wear boxers think their choice in underwear is bound by the eternal “Boxers or Briefs” query. Their popularity has largely faded due to the emergence of the boxer brief’s popularity and the increasing popularity of the trunk. While “laid back” might accurately portray a large number of boxer wearers, the only thing “laid back” is the boxer itself. By their construction alone, they are incompatible with today’s style of jeans and slacks, so how “laid back” are you supposed to feel with a ton of excess and needless fabric jammed into your low-rise jeans? Since I know people of all types of personalities that wear boxers, I won’t begin to try to make inferences about the “universal” boxer wearer. I’ll only say (for a plethora of reasons), the boxer wearer is an interesting breed, for sure.

Thongs: If you wear a thong like everyone else wears their favorite style typically possess the highest conscious when it comes to their underwear preferences. You probably got into thongs from your penchant for bikini briefs or jocks. Sure, you love the unparalleled support thongs provide, but curiosity about the design’s sex appeal was why you bought it in the first place. It’s also likely that you’re in tune with your sexuality and you’re willing to try just about anything in the bedroom.  However, thongs for men do come with a plethora of connotations, almost none of them positive. I am sure there are plenty of men who wear thongs who don’t have any inhibitions-which might not come as a surprise, given the highly-sexual nature of the style. But while it might take a “confident” man to purchase and wear a thong as every day wear, most of those men would likely tremble in embarrassment simply thinking about his co-workers or friends finding out. Surely, the negative connotation society has attached to the male thong requires the man who enjoys wearing them, to “rationalize” his preference, despite the style’s increasing popularity.

Jockstraps: If you wear a jockstrap as daily wear, you’re likely to be as comfortable with how you look in skimpy underwear as the man who wears a thong. The jockstrap’s no-coverage-of-the-rear design means that it’s at the highest end of the conscious scale in terms style choices. It’s prevalence as a design for every day wear is much more common among gay men, but as a straight man I can imagine that the majority of gay men are choosing a jockstrap to wear to their 9-5. It’s a design that was made for wear during rigorous activity such as playing sports or working out, so if you’re wearing it daily, you obviously love the support it offers you. It’s also probably safe to say that you’re extremely comfortable with your body and your sexuality. While I won’t claim that the jockstrap wearer is universally an “Alpha Male” type, if you enjoy wearing jockstraps, you love the feeling of masculinity the style provides.

So there was my attempt to provide (what seems to be) the only comprehensive guide to what your favorite underwear style says about how much you’ve thought about the most important piece of clothing in your wardrobe as well as providing you with an opportunity to see if your personality matches up with my perceptions about each style’s typical wearer. It was imperative that I avoid arbitrarily assigning perceptions about the people who wear each style; because I firmly believe doing so only serves to further the negative connotations that get assigned to various styles of underwear, or the people that wear them.

I’d love to hear your thoughts about this guide or the importance of treating negative connotations and stereotypes about various underwear styles with the cynicism they deserve, so feel free to email me at


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