I spent thirty-five years on the bra floor at Bloomingdale's 59th Street, and the running joke among the fitters was that we knew more about the men in our customers' lives than the customers did. Not because the husbands ever set foot in our department. Because the wives told us. They told us what he liked, what he wouldn't wear, what he kept buying in three-packs from the same drugstore for twenty years running. After enough of those conversations, you start to notice patterns. A man's underwear drawer is one of the more honest things in a household. He picked it himself. He's worn the same thing for decades. And what he chose, somewhere along the way, tells you a little about how he moves through the world.
This is not a personality test, and I am not suggesting any woman start sorting men by the contents of their dresser. It's about fit, comfort, and what those choices quietly signal. Small things, gently noticed.
The boxer guy
Loose-fit cotton boxers, the kind that come in plaid or solid colors with an elastic waistband and a button fly that nobody ever actually uses. This is the most popular style in America by a comfortable margin — the 2025 surveys I've looked at put boxers somewhere around forty percent of men's daily-wear preference, ahead of briefs and ahead of boxer briefs.
What does it tell you about him? He likes air. He doesn't want to think about his clothing once he's dressed. He probably sleeps in them. He values comfort over support and has decided, somewhere along the line, that whatever's going on underneath is going to be left to its own devices. There's a quiet confidence in that. He is also, in my experience, the man most likely to wear the same pair until his wife throws them out behind his back. The fabric goes thin at the seat, the elastic gives up, and he doesn't notice. Patrick was a boxers man. I threw out a navy plaid pair once that I'm pretty sure he had been wearing since the Reagan administration.
The briefs guy
The classic white brief, what you'd call a tighty-whitey if you were being unkind. Hanes, Fruit of the Loom, Jockey. Six to a pack. This is the style most men our age grew up in, and a good number of them never switched.
What does it tell you? He's practical. He likes support, he likes things to stay put, and he doesn't see any reason to fix what isn't broken. He probably has an opinion about how a t-shirt should be folded. He buys the same brand his father bought. And he is probably right that briefs do their job better than any other style for what he wants out of them — full support, no leg, no riding up. The interesting thing is that briefs have been quietly making a comeback in the last couple of years, with men in their twenties and thirties picking them up again after a generation of boxer briefs. Brands like Mack Weldon and Tommy John have rebuilt the brief in softer modal blends and contoured pouches, so the style your husband has worn since he was fourteen is suddenly being marketed as new again. It is not. He was right the whole time.
The boxer-briefs guy
The hybrid — brief-length leg, snug fit, full coverage. This is the style that took over American underwear drawers in the 1990s and 2000s. Calvin Klein gets a lot of the credit, fairly or not. For decades it was the default young-man's choice, and many of those young men are now in their fifties and still wearing them.
What does it tell you? He's self-aware. He notices fit. He understands that the same garment can be cut for support, length, and clean lines through a pair of trousers, all at once. He probably also notices the cut of his own shirts and how his pants break over his shoes. He is not vain, exactly. He is paying attention. SAXX, Mack Weldon, Tommy John, Bombas — most of the brands my son Michael's age group talks about are boxer-brief specialists, and they've added moisture-wicking fabrics, supportive pouches, and flat seams that the white-brief generation never bothered with. If he's switched to one of those in the last few years, he has joined the rest of us in the discovery that yes, the right undergarment really does make the day easier.
The trunk guy
A newer entry. A trunk is essentially a boxer brief with a shorter leg, cut closer to the body, designed to wear under slim trousers without bunching. Five or ten years ago you mostly saw them on younger men. Now they're showing up on men in their forties and fifties.
What does it tell you? He pays attention to silhouette. He's probably the one in the household who plans the outfit before he plans the day. There's nothing wrong with that. The trunk is a fine compromise between brief and boxer brief, and for a man with a leaner build it sits better than either. For larger men it can pinch at the thigh, which is something to know if you're buying as a gift. Always check the leg-opening width on the size chart.
The no-underwear guy
He exists. He'll tell you about it whether you want to know or not. There's not much to say here other than that the laundry runs more often.
What I actually want women to take from this
The reason I've thought about this enough to write a piece is that the same fit conversation I had with my customers for thirty-five years applies on the men's side. Most men have never been measured. They picked a style at fifteen, kept the size their mother bought them, and worked their way through life in something that was probably one waist size too tight by forty and one too loose by sixty. A drawer of underwear that doesn't fit is just as uncomfortable for him as a wrong-band-size bra is for you. The waistband digs, the leg rides up, the pouch doesn't support, and he calls it normal because he doesn't know any different.
If you're shopping for him — for a birthday, for Father's Day, for the box under the tree — here's what I'd suggest:
- Buy the style he already wears. This is not the moment to convert a forty-year boxers man into a trunk wearer. He will not thank you.
- Check the waist measurement on a pair that fits him, not the size on the package. Modern brands run differently than the Hanes from 1985. A 36 in one brand is a 34 in another.
- Stick to cotton or a cotton-modal blend for everyday wear. Synthetic performance fabrics are wonderful for the gym and not so wonderful for sitting in a recliner.
- Replace, don't add. Get rid of three old pairs for every three new ones. Otherwise the drawer becomes an archaeology dig.
- Don't make it a comment on his body. A new pack of underwear is a gift. A new pack of shaping underwear is a project he didn't sign up for.
One last note
What his underwear says about him, in the end, is just what he's comfortable with. Some men want to feel held together; some men want to forget the whole thing is there. Both are fine. The mistake is staying in a style or a size that hasn't fit in a decade because nobody ever told him there was another option. You can be the person who tells him. Gently. Maybe at the laundromat. That's where most of my best conversations have happened.