Quick yes or no- Should a non-athlete wear a letterman jacket for a date in college in 2016?
The girl will say "omg why are you wearing a lteerman jacket that's so weird ahahha" and then never mention it again and it will not affect her opinion of you at all
You're not a Highschool athlete so its strange but it isn't a big deal, but I personally wouldn't
Good luck on your date
I like letterman inspired stuff. But a straight up letterman jacket is for jooci highschool boys, not grown ass men. And even if you were in highschool wearing it on a date would be something a tool does.