Emoticons ruined the internet and in no way should be glorified.

"ruined" might be a bit harsh. I mean you're still here right? I like the way you've used the space and your use of proportions and placement. I'd tend to agree that I find emoticons a little annoying though.

why not use colour? The design is simple and something needs to make it stand out.
I think taking a 2nd look at how the design sits on the tee may also be a good idea... is that the most flattering formation of the emoticons?

But I like the idea.

Terribly random placement. I know that was your point, but you gotta make them prettier for a shirt...maybe using different colors and draping them over the tee like the Matrix vertical numbers?