Comedy

The 20 Worst T-Shirt Fails

posted August 25, 2011 by Cory Gershon

20 Worst T-shirts Cover

"Bro, you should totally wear your 'boob inspector' shirt to the breast cancer survivor's walk." It's amazing the logic that goes through some people's minds when they get dressed in the morning. But hey, their fail is your win, so let's relish the poor decisions of others, shall we?

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1

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/t-shirts-cover.jpg

"Bro, you should totally wear your 'boob inspector' shirt to the breast cancer survivor's walk." It's amazing the logic that goes through some people's minds when they get dressed in the morning. But hey, their fail is your win, so let's relish the poor decisions of others, shall we?
2

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/fail_shirt_black_woman.jpg

"Shiiiiit, you don't want none of this."
3

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/t-shirt_with_grandma.jpg

This just might kill grandma.
4

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/drink_till_you_want_me.jpg

If she's lucky, she'll blackout and not remember anything.
5

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/daddy_bj.jpg

Women...always so controlling.
6

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/kid_on_shoulders.jpg

Now this is just wrong.
7

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/racist-tshirt.jpg

For those with a hatred of minorities, but a bursting love of rainbows.
8

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/buy_dad_beer.jpg

Kinda doubt he'll be getting his wish anytime soon.
9

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/body_t-shirt.jpg

With an ass like that you wouldn't think her calves would be so big. Oh, wait...
10

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/go_to_jail.jpg

This guy must be able to predict the future with that shirt.
11

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/i_love_ny.jpg

Not falling for that trick again.
12

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/muff_diver.jpg

"Daddy, whats a muff diver?"
13

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/nazi-kid.jpg

And you thought you had it rough fitting in as a teenager...
14

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/terrorist.jpg

Talk about ironic.
15

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/odam_fcked_her.jpg

He was the first pick in the NBA draft, we figured he did already.
16

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/porn-star-t-shirt.jpg

If you just threw up in your mouth a little bit, you're not alone.
17

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/old_dude_shirt.jpg

Yet, another testament that old people just don't give a f%&k.
18

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/out_on_bail.jpg

This was probably taken two days before he went back to jail.
19

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/i_beat_anorexia.jpg

Such an inspiration.
20

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/tore_mommy_a_new_one.jpg

Look at the size of that head, it just looks painful!!
21

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/not_flat_in_florida.jpg

This is actually more "win" than "fail".
22

http://media.heavy.com/gallery/the-20-worst-inappropriate-t-shirts/20-worst-3.jpg

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The 20 Worst T-Shirt Fails

Tags: 20 Worst, Comedy, Fail