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Old Mens Underwear Ads: A Frightening Fashion Retrospective

Today, we take for granted the fact that our underwear is comfortable, breathable, and properly fitted—but the modern menswear is actually the product of years of strategic engineering. So, take a moment to enjoy a century’s worth of underwear that you will never have to wear (again).


At the turn of the 20th century, the aspiring men of leisure wanted something new from their underwear—mostly, that it not be held up by bulky or unreliable drawstrings. Solution? Full-body underwear, supported by your shoulders. It’s not fitted. It’s not even comfortable, but it lets you stride forward knowing that your underwear isn’t going anywhere, even under your bargain $25 suit.

And if your family is into spontaneous, circus-inspired, underwear-clad feats of strength…well this was the era for you.

1900's full-body underwear, supported by your shoulders


1910 mens underwear advertisement sample

This decade ushered in new designs for slightly-better-fitted full-body underwear, for men who want to feel like serious athletes, even when they’re standing around, inexplicably holding watering cans in a thoughtful manner. (Lifestyle choice or awkward metaphor? We’ll never know.)

This was also the memorable decade in which men first feel compelled to have deep and emotionally profound discussions about their underwear, in their underwear. Because, if you can’t talk about your repressed feelings, you can always talk about non-chafing quality cottons…


The era of awkward metaphor continues into the 1920s, which appeals to the man who enjoys standing around in his underwear and contemplating his riding crop. As one does. Unless one prefers showing off one’s dumbbells…or giant spear?

mens full body underwear

This decade was also a big era for underwear-adjacent ads, marketing healthful solutions to the man who wants to look slimmer and more athletic in his skivvies. Point of clarification: in the 1920s “healthful,” traditionally meant “absurdly unrealistic” or, more often, “likely to result in your untimely demise.” (Side effects may include spontaneous gender alteration.)

1920's losing weight advertisements


The radical 1930s saw men embrace the idea that underwear does not have to be knee-length to be awesome. Whether you’re hosting a “sweater vests v. skivvies” badminton party or just fantasizing about Mr. 1937’s support system, this is an era in which underwear inspires nothing but pride.

mens underwear onesie

Wait…isn’t that cut-out almost like an x-ray? X-ray vision? That’s almost like a superpower…and do you know what would be really super? Underwear as outerwear! And in color!

superman in colorful underwear advertisement


The 1940s seemed torn between the idea that awesome underwear makes you feel like flying, and the return to men who have profound discussions about their underwear, in their underwear, as men do.…when they’re not resolving their differences with manly pillow fight frolics.

1940s underwear advertisment


The stoic 1950s saw more hearty manly banter on the underwear front, and a gleeful mockery of the underwear from previous generations. But it’s the Biblical allusion that really clinches the deal—because if fig leaves were good enough for Adam, then stretchy cotton is good enough for us. (Advertising logic at its finest.)

1950s mens underwear advertisement

Unfortunately, the 1950s also introduced a whole new era in extremely creepy boy’s underwear advertisements. But whether you’re raising an aspiring banker, or the tiny gangster who’s planning the next great bank heist…this underwear supports all your parenting choices.

1950s boys underwear marketing ad kid sticking gun in underwear


For a moment, underwear advertisements spoke to the heart of the hippy movement—men holding flowers and feeling that heady high that comes from superior underpants. But, as it turns out, hippies weren’t big on underwear, and they soon figured out that smoking the “flowers” produced an even better high. Advertising fail.

1960s flower power mens underwear ad - man holding a bouquet of flowers

Never daunted, the underwear makers turned to a more receptive audience. An audience inexplicably comprised of crossing guards, hillbillies, and…Santa’s little helpers? Perhaps it wasn’t just the hippies who were smoking the funny flowers.

1960s fruit of the loom mens underwear advertisments


Oh, the 1970s. You want to write something snarky, but the original copy is hard to beat. Who needs dignity, when you can have Underflair!

1970s Underflair mens underwear advertisement

You have to wonder whether the whole decade was an extended fashion parody, sprinkled with chest hair and wrapped in a slinky, leopard-print Lycra unitard.

hairy men and leopard skin underwear onesie

On the plus side—a breakthrough in racial diversity.


The ‘80s tied it all together—burlier than the hippies, but more colorful than their forefathers, rocking the underwear parties, still loving all things synthetic. They seem to be a little unclear on whether the whole “fig leaf” thing was literal or metaphorical (or what a fig leaf actually looked like), but they’re muscular enough to beat you up if you mock their fashion choices.

1980s underwear advertisement


And although men had been contemplating and celebrating their underwear in groups for the better part of a century, the ‘90s saw a big push for solo underwear adverts. Just you and your ego.

1990s mens underwear marketing advertisement

Because nothing says “understated” quite like shiny turquoise briefs.

So, the next time you step out of the shower and into a new morning, take a moment to remember the underpants of yore…then thank the universe for breathable fabrics and elastic waistbands. Because whole generations of underwear models suffered horrifying indignities to get us where we are today.

Otero Menswear. Anything But Average.

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