[Custommods]

If i was to make a shirt that said "programming is for cool kids" as an example, using halvetica font, and some one was to recreate the shirt same sizes with minimal differences using "times roman" font, would i be able to pursue them legally?

 

[kimura-mma]

You can try, but it would be very difficult.

The phrase itself is not eligible for copyright. Only the exact design can be copyrighted. So you couldn't prevent anyone from using a different version of the design (in this case, using their version of the phrase).

The phrase could be eligible for trademark. But you would need to be using it as a brand name, not just a t-shirt design.