I made my first attempt to brave the crowd in the cosplay area of Comiket this year, since on day 3 I had plenty of time while one of my friends picked up his millions of porn doujinshi. I'd say it looks like any other event in the West, only with the more strict rules about props. Saw plenty of men crossplaying, too. Even a huge gaggle of guys dressed as Touhou charas. So, my friend and I are going to return in winter crossplayed as Rozen Maidens.
Even with my earlier statement of the high turnover rate of shows getting old, there were still plenty of Sailor Moon cosplayers there at Comiket 74. I think if you happen to be going to Comic Market and are a mature adult, feel free to cosplay, just don't expect it to be a hyper fun lose-your-mind-go-crazy party like american conventions tend to be. It's a very relaxed time.
If you don't know japanese, just look around, your fellow gaijin stand out well enough.. ask them for directions.