I spent thirty-five years on the fit floor at Bloomingdale's, and most of those years were on the women's side. But every Christmas season the husbands would come over from the men's department, holding three packs of whatever their wife usually bought them, looking lost. I'd send them back with one piece of advice: stop buying the same three-pack you've worn since 1985, and start thinking about fit and fabric the way a tailor thinks about a suit.
Men's underwear is having a quiet little renaissance, and a lot of it is good news for gentlemen on the older side of sixty. The fabrics breathe better. The waistbands don't dig. The cuts actually account for the fact that a sixty-eight-year-old body is not a twenty-eight-year-old body. So if you, or the husband, or the son who calls on Sundays, are still pulling on the same style you've worn since the Carter administration, here's a plain-spoken tour.
Start with the body, not the rack
Same thing I tell the gals in the bra department. Before you pick a style, take honest stock of three things: what your waist actually measures (not what it measured in 1988), where you carry your weight, and what you do all day. A man who walks the dog for an hour gets a different answer than a man who sits at the kitchen table doing crosswords. There is no single best men's underwear. There is a best one for you, today, at this weight, in this season.
Wash a pair before you decide it doesn't fit, by the way. Cotton tightens up a touch on the first wash. Don't return them after one try-on in the bedroom mirror.
The styles, plain English
Boxer briefs
The workhorse. Snug like a brief, leg coverage like a short. They sit on the upper thigh and hold things where they belong without binding. For most men over sixty, this is the safe first pick, especially if you've started feeling the seam of an old pair of boxers ride up. Look for a four to six inch inseam if you're shorter, six to eight if you've got the leg for it. Industry surveys this year put boxer briefs and trunks among the top three preferred styles, and there's a reason. They work.
Trunks
Think of a trunk as a boxer brief with the leg cut shorter, sitting on the high thigh rather than mid-thigh. Trim, modern, sits cleanly under a slim trouser. If you've lost a little weight and your old boxer briefs are bunching, a trunk is often the answer. The leg opening doesn't ride.
Briefs
What everyone over sixty grew up calling tighty-whities. They never really left, and the manufacturers have quietly improved them: better elastic, softer cotton, sometimes a contour pouch instead of the old flat front. Briefs are still the most supportive style on the rack and the easiest to layer under a thin summer trouser without lines showing through. Don't write them off because of the nickname. A good brief in a navy or heather grey looks like an undergarment, not a billboard.
Boxers
The loose, woven kind. Like a tiny pair of shorts. Cool in summer, easy on the skin, and lovely for sleeping in. The honest downside at our age: they don't support much. If you find yourself adjusting on the walk to the mailbox, that's the boxer telling you it isn't doing its job for daytime. Keep a couple of pairs for around the house and the warmest nights, and pick something snugger for errands.
Long underwear (longjohns)
Don't laugh. If you live anywhere there's a real winter, a thin pair of merino or modal long underwear under your trousers is the most comfortable thing you'll own from November to March. The old waffle-weave cotton is gone in the better lines. The new stuff is fitted, thin, and warm.
Short-leg long underwear (so-called "shortjohns")
Half-length long underwear, ending above the knee. A good middle layer for fall and spring, or under a suit pant on a cold travel day. Skip them in summer.
Thongs and similar minimal styles
They exist for men. I'm not the one to convince you for or against. I'll say what I say in the bra fitting room when someone asks about a thong at sixty-five: if it's comfortable for you, fine; if it isn't, there are a hundred other things on the rack. No moral weight either way.
Going without
I get asked this. Skin contact against an unwashed trouser seam is a recipe for chafing, especially in summer, and the trouser does most of the wearing out. A clean, breathable pair of underwear is a small piece of laundry that saves a large piece of laundry. That's not a lecture, that's just arithmetic at the washing machine.
Fabric matters more than style
This is where I'd spend your money before I'd spend it on a fancy cut.
- Combed cotton or pima cotton. The classic. Soft, breathable, easy to launder. Choose a heavier weight if you want them to last; the thin discount packs go limp after a season.
- Modal. A beech-wood fiber that drapes softer than cotton and pulls moisture away from the skin better. A modal-cotton blend is, in my opinion, the sweet spot for a sixty-plus gentleman. Holds shape, doesn't itch, doesn't cling on a humid August day in Queens.
- Bamboo. Cool, soft, antimicrobial. Pricier. Worth it for a few pairs if you walk a lot or live somewhere warm.
- Performance synthetics (polyester, nylon blends). Made for moisture-wicking. Lovely for the gym or a long walk. Less lovely as everyday wear, because they don't breathe the same way.
Whatever the fiber, look for a touch of spandex or elastane, usually four to six percent. That's what gives modern underwear its stay-put quality without the old-fashioned squeeze.
The waistband is the part most men get wrong
If you take one thing from this column, take this. The waistband does more work than the rest of the garment combined. After a certain age the abdomen softens, the waist shifts a bit, and a waistband that's too tight leaves a red ring you can still see two hours after you take the underwear off. That's not just uncomfortable, it's a sign the elastic is fighting you.
Look for a wide, soft waistband — an inch and a quarter or wider — and one that doesn't curl when you bend over. The good brands now make a no-roll, brushed-back waistband that sits flat. If your current pair has a thin, hard elastic that's started to fray, replace them. Don't keep wearing them because they're "broken in." Broken in usually means broken.
What to actually buy this week
If you (or he) needs a starter drawer at sixty-five, here's what I'd put in it:
- Six pairs of modal-cotton boxer briefs in dark neutrals (black, navy, charcoal) for everyday.
- Three pairs of cotton briefs in white or grey for layering under summer slacks.
- Two pairs of woven cotton boxers for sleeping and around the house.
- Two pairs of thin merino or modal long underwear if your winters are real.
That's it. Replace anything older than two years, anything with stretched elastic, and anything you reach for last in the drawer because you secretly don't like it. Life is too short to wear underwear you don't like. I tell the gals that about bras. It is just as true for the men.
Take care of the waistband, mind the fabric, and let the style follow your body, not the other way around. The right pair, you forget you have on. That's the whole job.