1) It is often deprecating to say that a female celebrity looks like a transvestite. The reason is that a transvestite often needs a lot of makeup and other cosmetics to do to look like a woman, and that it often can still be seen. It might even be obvious, once you know it. To say that an actress looks like a transvestite could mean that she would also need a lot of makeup to look fine (suggesting that she would actually not look fine at all without the makeup). On the other side, a transvestite could also be a kind of "exaggerated" woman. In this sense, a celebrity looking like a transvestite could be someone acting as the exaggerated prototype of a woman. Also, the transvestite looks contains some elements of gender ambivalence (androgyny). 2) Usually, it is rather the other way round: some transvestites try to imitate particular actresses, singers or other celebrities: "Many of these drag queens impersonate specific actresses and pop divas such as Beyoncé, Cher, Madonna, Charo, Donna Summer, Céline Dion, Diana Ross, Tina Turner, Patti LaBelle, Shirley Bassey and others, emulating their high-fashion costuming and jewelry. Drag artist John Epperson has used the persona Lypsinka as a caricature of Joan Crawford, including in his play The Passion of the Crawford." Source and further information: http://en.wikipedia.org/wiki/Drag_queen 3) "Megan Fox thinks she looks like Alan Alda -- a transvestite version of frickin' Alan Alda." Source and further information: http://www.tmz.com/2009/01/12/megan-fox-im-an-insecure-transvestite/ 4) "Christina Aguilera or Transvestite? It's time for America's favorite game show - "Christina Aguilera or Tranny?" Make your guess, then click the image!..." Source and further information: http://cityrag.blogs.com/main/2008/05/christina-aguil.html

Probably unknown to most, especially those outside the UK, but an actress called Fay Ripley and the lead singer in a band called Florence And The Machine.

Well, she is a celebrity of sorts. In a twist of irony, I would say that Shirley Phelps Roper of Westboro Baptist Church looks like a transvestite: http://images.google.com/images?hl=en&q=Shirley%20Phelps&sourceid=navclient-ff&rlz=1B3GGGL_enUS291US291&um=1&ie=UTF-8&sa=N&tab=wi