my friend Josh looks FABULICIOUS in lolita. He's even a bit heavyset. He had a friend make a custom brocade for his dress, and he wears heels better than I ever could... T______T I'm so unfeminine for a female. *kicks stupid weak ankles*
So yes, if you have the body to pull it off, then go for it!!! I've seen some really not feminine guys in lolita with super nice dresses too, so I give them some kudos too for having beautiful outfits.
GO GO GO!!! *cheers you on*