Would only wear a #retro effort or something just old.
That "half your age plus 7" rule for relationships should also apply to football tops imo. I'm 26 so only 20 year old tops for me. The 1996-1998 Frikin Brewery top is my favorite that I wear all the time.
Also important to make sure you never wear anything even approaching matching top, shorts and socks. Even at fives it's crucial that there's no chance of anyone even mistaking you for a #FullKitWanker. I've kept a set of generic bright yellow football socks which solves when wearing Dundee or Scotland attire.