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29 answers

OK wel if you wanna look classy wear a cocktail dress similar to the first three links i gave you!
If you want to look simple look at the fourth one i gave you a pink poplin top paired with a pencil skirt! Then you can pair it with a black shoe like this (5th link)

2006-08-11 00:10:56 · answer #1 · answered by Anonymous · 1 0

Even if you're a cross dresser if you accept it as a date with a guy be nice and wear something "normal" (i still don't know who has the right to define that word,lol) but if he knows you're a cross dresser and you accept it as dinner with a friend,wear what you like or simple ask him!

2006-08-11 06:56:39 · answer #2 · answered by lushnut 69 1 · 1 0

Above all it is important that you are comfortable.

If he doesnt know that you cross-dress yet, I would wear something that hints at it, not full on, but something masculine that could be accepted as normal wear for a woman. You dont want to scare him off by turning up suited and booted. He's more likely to accept it if you ease him into the idea.

2006-08-11 07:00:01 · answer #3 · answered by Suzi O 2 · 0 0

Don't show to much skin, leave some to the imagination, if your wearing skirt cover the top a little bit, and if the top shows a little cleavage try wearing shorts, don't overdress too much or too casual you want to appear sexy not needy and tarty. Maybe try opting for a girly dress not too short with a little cardi over it.Good luck

2006-08-11 07:04:38 · answer #4 · answered by Emiliana 3 · 0 0

Does he know that you are a cross dresser? If so wear what you feel comfortable in.

2006-08-11 06:51:24 · answer #5 · answered by Cake 2 · 2 0

it depends on so many factors.
A. does he know you cross dress?
B. does he think you are female?
C. are you passable?
D. where are you going for dinner and what's the lighting like?
E. are you intending this to be a long term relationship or just a one night stand?
F. have you been out dressed in public before?

2006-08-11 09:34:13 · answer #6 · answered by bobbi b 3 · 0 0

Dress in something that makes you comfortable. Stylish,but comfortable. If you like dresses,then wear a dress. The corset dresses are really pretty.

2006-08-11 08:48:42 · answer #7 · answered by Deerrunner 6 · 0 0

when deciding whether to ask you out he will of course taken a look at what style of dress you choose so i would suggest maybe accessorise with something from your 'other' wardrobe,,giving a hint of the fact you also like another way of dressing,,its a bonus if he asks,,this applies really if you want him to know about your dress sense and could lead to other conversations regarding your likes and dislikes,,same for him.

2006-08-11 06:56:56 · answer #8 · answered by lex 5 · 1 0

something totally chick, maybe a little black, PLAUIN dress, with a few defined accsessories, or some tight, dark blue jeans with the sexy white top, not a t-shirt, but a little strappy thing, go with that!

2006-08-11 07:00:57 · answer #9 · answered by abbie 2 · 0 0

Dont wear your clothes back to front- that just looks silly and Kris Kros didn't last too long by doing it

2006-08-11 06:51:06 · answer #10 · answered by larry365 3 · 2 0

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