Top 10 Awkward Underwear Photos

There are a gazillion awkward underwear photos on the interwebs. We’ve perused through at least half a gazillion to bring you our Top 10 Most Akward Underwear Photos of All Time! You can thank us later.

In our awkward underwear photos gallery we have some celebrity favorites (how could we not include Sacha Baron Cohen?) as well as some just plain crazy pictures. We even bring back an old underwear magazine photo from the (70’s) for you to prove that underwear has been awkward since at least¬†then. Since celebrity underwear sightings are all the rage these days, we were sure to include an awkward celebrity photo, too (although you may have a hard time telling him apart from Sacha).

Which awkward underwear photo is your favorite?

Dear Mr. Hefner, please let me model for you. Please?!

I don’t know why I’m here or how this underwear is staying on, but I guess I’ll serve face anyways.


Mmmm… fruit.


You down to party?


We’re thrilled to be D and G. No, really. Thrilled! I mean, who doesn’t LOVE an underwear onesie?


Wa wa Wee wa!


We we Waa we!


You come here. You give me hug. You pull up my pants.


Believe it or not, I was voted most likely to be a bachelor.


Hey, girl. I told you I’d fill out my briefs and keep you safe. You knew exactly what you were signing up for.