I actually find "Too Big to Fail" kind of ambiguous ... that's why it's fun. I'd wear it (and I am not the type to go bragging about my size).
Then again, with my build, people would be unsure what exactly the "too big" is referring to. I think if a skinny guy wore that shirt, it'd be a lot more suggestive.
I find shirts that brag explicitly (like the footlong one with the arrow pointing down) to be obnoxious. I wouldn't wear one like that outside the house ... although my wife likes them on me! :smile:
Steve