I think I’d dress pretty much the way I do now (I do love my flares!), but with more T-shirts, bigger shoes, and definitely commando. Head shaved.
And a tuxedo at least once, just to see how I look.
I’d probably spend a few weeks dressing as slutty as I could without having to do dry cleaning, but I’d eventually get bored and go back to jeans and t-shirts, clothes I don’t have to think about. Somewhere in the back of my closet would be an evening gown with concrete or grease stains on it from one of the times I forgot to change.
Chinos, plaid shirts, sweaters, tweed jackets. (I usually wear a skirt or dress to work, but with dark tights and flat shoes, so this seems like the male equivalent of that.)
Vastly overrated. All it takes is one time having to twist suddenly whilst walking up a flight of stairs, and it’s not a fashion statement you’re likely to make again.
I’m a jeans-and-flannel-shirt guy in the winter, cutoffs-and-t-shirt in the summer. If I were a woman, I doubt that that would change, but I’d probably be more careful that the t-shirts were opaque.
I don’t go commando now, but I might as a woman, since I wouldn’t have the sort of naughty bits that flop about. I hope I’d be sufficiently flat-chested that I could eschew bras away from work. My sisters are, so if I’d been born female, that would have probably been the case for me too.
I would definately shave my head. If I had hair on my back, I’d shave that too.
Whatever attracts lesbians… 
d&r
Well, I admit that my first thought at seeing the thread title was “Woo hoo! Micro-skirts and tight sweaters! Seamed stockings, garters, and five-inch heels! Are they still making hotpants these days?”
But then I realized that the likely transfiguration for an in-pretty-good-shape-for-his-age-41-year-old-man would be into an in-pretty-good-shape-for-her-age-41-year-old-woman and not a 19-year-old supermodel.
So, um, pleated slacks and sensible heels and turtlenecks and pearl earrings.
Shit.
Nothing.
I’d be too busy with my fiance.
:O~~~
For the first month or so, nothing - I’d be checking msyelf out all day. After that, I’d wear those jeans - I think they’re called hip huggers? For a shirt, I’d wear one of those hankercheif tops that I see at clubs all the time. I’d also probably take a whole lot of pictures in case I switched back to being male.
Oh, I don’t wear undergarments now so I probably wouldn’t wear them as a girl either.
You know, I sometimes worry about this, because I think if I suddenly turned into a guy, buying clothes would be stressful.
I’m a skirt and sweater-set kind of girl, so the guy version of that would be chinos with shirt and tie, right? Or I’d be that guy in your office who wears a suit, but you never see him with the suit jacket on. I’d always have nice shoes, I love men’s shoes. And a lot of Versace. It would be so much fun to shop for a really great men’s top coat, too. And a trench coat. I sort of have a thing for men’s outerwear.
Hey, can I be taller?
Thank goodness I went to Catholic school – so I had to learn how to tie a necktie to help my little brother get ready for school.
Miniskirts, silk blouses, bustiers, and fuck me heels.
Exactly what I’ve got on now - Doc Martins, jeans and my husbands shirt.
Hey if I suddenly become a guy do I get to keep my husband?
A Kilt and all the trappings needed to wear one.
I agree with Incubus, there is a huge variety of women’s clothes, and it’s not just for formal wear either. The deal would have to be long-term for me, just so I have enough time to try out everything I can find.
yeah docs-9 hole, jeans, t-shirts, sweaters. casual wear.
if I had to dress up- something from zara, nice shoes, leather jacket.
Well if my sexual prefferences didn’t change with becoming a woman, I’d probably wear more masculin clothes than I do as a man. I’d deffinately go in for that Lesbien Chique vibe. But with a serious girl friend I’d try out all that lovely revealing stuff women get to wear if they want to.
Cheers, Bippy
add me to the ‘total slut’ gang: push up bra, cleavage exposure, short skirt, skimpy panties, etc. Then I’d hang out in the women’s locker room and check things out.
I would wear a suit whenever possible, because there is nothing sexier than a good looking guy in a nice suit. I would have a goatee too.
Boxers or boxer briefs
Jeans
White T-shirt
Bowling shirt open over that
Vans or Docs
Little necklace with a pendant that rests at the base of my throat
A nice, lowkey cologne
Short, spiky haircut
Goatee
I hope I’d look a little on the edgier side of “Backstreet Boy”.