I have definitely done that. Most times I wear a guy shirt when I leave the house and take it off when I get a mile or two away. I wear a cami or racerback and work on tanning my upper arms to match the lower.
I have also pedaled totally girly, with makeup, and girly hair. I never know what reaction I'll get when I go thru a construction zone and all the guys are looking at me. Are they looking at the great legs (just kidding) or at the mannish looking person?
I go out 2 or 3 times a month, I guess.