It's all in your comfort needs (both physical and psychological). Personally, I can't stand to ride more than a couple of miles in anything except "real" cycling shorts--it's just not comfortable to me. At the same time, at 5'9" and 250 lbs., I'm not incredibly comfortable in the way I look when I'm wearing them. For me, the physical comfort far outweighs the psychological discomfort. As evidenced by some other recent threads in this forum, though, some people project their gender identity issues onto others who wear the lycra/spandex clothing, so factor that in if it's something that'll cause you concern.