I would opt for #2. The "bro" thing ruined #1 for me.
 
I'll agree with the other guys on option #2, but I'd say look at t-shirts from companies like LinkSoul, TravisMathew, Matte Grey or even Adidas or Nike, etc if he's into any of those brands instead.
 
Between the two, shirt number two.
 
#2 gets my vote as well.
 
I'd say the 2nd shirt


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