25 of the Most Ridiculous Vintage Underwear Ads

By: Christopher Harrity
3.30.2014

Men's underpants can be both mysterious and confounding. Selling them in magazines obviously posed problems of context and decency. In an effort to keep things light, many ads ended up going to dark and fetid places. Places you should avoid. Other ads went deep into the wedgie of the double entendre, hopefully blindly. And some ads are simply fun to gawk over. Enjoy!

Scary chasity underwear. "The New Order" indeed.

 

 


Inches? A nudist colony? Mild support? Looks like a locker room dust-up about to explode!

 

 

Really, Hank, you don't have to play the towel-snapping game now. No one else is here. As soon as I fasten this garter I am going to kiss you very quickly and madly.

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