I’m not sure that seeing men in their underwear is ever anything but ridiculous (with certain Calvin Klein ads being the stark exception). But when you throw in some vintage hair styles and vintage attitudes, then you cross the line from ridiculous into hilarious. All these vintage men’s underwear ads are funny for different reasons, but they’re bound to get you laughing.

24 Men’s Vintage Underwear Ads That Are Totes Hilarious

#1: Tighty-whities are so square, man.

#2: Whatever color or print you choose, the important thing is to make sure your undershirt is tucked into your briefs.

#3: The essential “drop seat” underwear for playing leap frog with your man friends.

#4: With that mesh knit, you can use your underwear to catch fish if you’re ever stranded on a desert island.

#5: In the 70s, matching your shirt to your briefs was #winning.

#6: Unfortunately, this print just looks like the kind of marks you never want to see on underwear.

#7: What kind of “business” are these guys in?

#8: You know, the perfect underclothes for sitting around in while you sip your tea.

#9: They may keep their fit, but sticking a cap-gun down the front of your undies just seems like a bad idea.

#10: That book looks waaaay too serious for a dude sitting around in his sunshine colored briefs.

#11: If you’re going to wear your undies to the beach, make sure to take your shades. They make this look work!

#12: What’s up with underwear models carrying people on their backs?

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