Von Teese is amazing, I was on board until you said that
It depends entirely on the individual. Many cases of gender dysphoria are diagnosed before the onset of puberty, in which case the use of female hormones can prevent the development of male physical characteristics (deep voice, Adam's apple, skin thickening) and facilitate female characteristics (thinner skin, wider hips, natural breasts). It's all dependent on the inherent genetic characteristics of the individual, as some men look quite feminine anyway - this is particularly true of Asians.
It doesn't matter if 90% of transgender individuals aren't at all convincing - and I'm not suggesting that percentage is accurate for a second - if he married one of the 10% who are virtually indistinguishable from genetic women. You've also got to consider that many women have a boyish, masculine appearance anyway.
At the end of the day beauty is subjective; afterall, there are many who consider Paris Hilton and Dita Von Tease to be attractive!