There was a period (1965-1975) when men's fashion was fun. Colorful, experimental and fun.
I lived through that period and exploited its sartorial freedom for gender-bending. In 1973 I wore a top to high school that was sold as male clothing, but man, it was wild! Skin-tight knit fabric with brightly-colored floral design and a thick, brown elastic band around the waist -- which left 3-4 inches of skin exposed between it and my pants. Even teachers noticed and commented on it (negatively).
Here's another example from that time. Thoughts?