I'm 6'4" 255lbs and have never even thought of passing but I still wear a lot of women's clothes. Fortunately I wear size 10.5 mens shoe which means there is a substantial choice of size 12 womens shoes to choose from if you know where to look. Lane Bryant, Payless and Avenue have a nice selection of shoes, boots and sandals up to size 13 and all in wide width. I love tall boots and wear them with jeans no problem.
Size 20 tall womens jeans fit me perfectly so that is all I own and wear. Lane Bryant, Avenue and Eddie Bauer have some great jeans and pants which make up most of my day to day wardrobe. I can even squeeze into some 18 Tall skinny jeans if I really want to femme things up.
I do have trouble with women's tops. Even tall lengths from Eddie Bauer are not long enough and ride up. I have found many tunic length tops from Jessica London will work for me. I also have several tall sweaters from Eddie Bauer which I can stretch and wear.
Althought I have not ordered from them, there is a company called LEL (long elegant legs) which sells really hot womens jeans and pants but they are a bit pricey.
It would be nice to be 8-10 inches shorter but I have figured out how to make things work for me.
