Ann Boleyn Ladies Pants, £16.00 at Five Go Mad
These may well be the most wonderful panties we’ve ever seen. But between the granny cut and the portrait of a woman whose husband had her beheaded after she failed to bear him a son, this pair is sure to kill the mood, so to speak. Also available: Elizabeth I (a.k.a. “The Virgin Queen”) on your crotch, Henry VIII (unfortunately, not the version played by Jonathan Rhys Meyers) on your butt.
Mr. Octopants Underwear, $12.50 at Etsy
If you look closely, you’ll see that the adorable octopus on these boxer-briefs only has seven pink tentacles. The eighth one is… yup, you guessed it. Three words: trying too hard.
Uterus Print Panties, $8 at Etsy
These underpants are wonderful, both in idea and execution. But just try and look at them without thinking about the reproductive system, getting pregnant, etc.
“Don’t Turn These Inside Out Again” Boxer Briefs, $20 at Etsy
Witty, sure. True? Yes, sadly, we’re betting this reminder would be helpful to a fair number of dudes. And yet, shockingly, most women don’t consider dirty underwear a big turn-on.
Something Blue Boyshorts, $25 at Brooklyn Fox
If you really are getting married, we can’t think of a better choice of undergarment. If not, get ready for a moment of extreme awkwardness.
Hairy Panties, €29.50 at Nutty Tarts
These are certainly stylish and funny. But didn’t you want to leave something to the imagination?
Bromance Underpants, $15 at Etsy
These boxers, featuring a Victorian-esque image of two men who look like they’re mere moments away from a lip lock, would probably go over big in bed on a gay man. If you’re trying to bed a lady, though, they’re just about the quickest way to sow major, “Do we have a future?”-style doubts.
Keyhole Panties, $12 at Etsy
Seriously? You’ve got to have a key to get those off? Sounds a bit high-maintenance, huh?
Eggs and Bacon Boxer-Briefs, $30 at Etsy
This looks delicious — so delicious, in fact, that it might well convince your drunken hook-up that she’d rather do a late-night diner run than, well, you.
Friday Night Fabulous Panties, $42-44 at Sexy Period
Sure, these looks fairly appropriate for the boudoir. But then you realize that they were designed as “backup to be worn in addition to your regular sanitary pad and tampon routine.” Might not want to take them off, then, huh?