So, you put on clothes not designated for your initially assigned gender...

[LaPapito]

"Then you have achieved that which you have set out to achieve," You are the cigar who is just that...a cigar...nothing more...nothing less...meaning; you are just a man wearing a womans dress just because...nothing more...nothing less...! But others don't feel this...Ergo [sometimes], "a cigar is not just a cigar..."

However you did stress something...and I think this is your real issue...just because you wear a dress, does not mean you are attracted to men [because you associate yourself as a male] fine...soo then the real problem is that you are probably being approached by men in clubs because you are dressed in "drag" [to be used loosely here]...which impels me to ask two questions...[1]what type of club are you wearing your dress to and [2] are you a closet dresser [meaning] are you out to female friends, and are they comfortable with your so-called "cross-dressing...?"

[barbie]

Although all of clothes I have purchased during the past 7 years are women's, there are many types of women clothes I do not like and do not purchase. In terms of aesthetics, I do not like those for aged women's. And I do not purchase bikini, becuase it is practically inappropriate for me to wear outdoors. I do not purchase too long skirts, because I think they are not sexy.

So, my answer is "aesthetics + practicality".

Barbie~~

[VelindaSalazar]

Why do I wear clothing that is not designated for my initially assigned gender?  Originally, it was because I wanted to be a girl.  It became a fetish as I aged.  Finally, it was just clothes I enjoy wearing.  It's all about fashion and usability.

[PhSensei]

For me my clothing choices are about what makes me feel good and what makes me feel sexy.

I'm a male, and happily do traditional male things.  But my balance for that is to slip into something silky and or frilly later.  I'm trying to balance the yin and yang and clothing is how I express myself.  I do not try or even hope to pass, I just like to feel good.

I never feel sexy in male clothes.  The female for is what attracts me and I think I emulate what I can of that by my clothing choices.  I know I look like a guy in a dress.... but again it makes me happy

[Rebecca.R]

I ticked the second option.  I feel that I have far more 'traditional' female traits (nurturer) than male traits (hunter) and so I wear clothes that I perceive to fit the inside me.  I feel relaxed and comfortable when I wear them.  If society was different I would wear them all of the time.  As I have a family I take their feelings and concerns into consideration and keep this side of me to myself. (And you lovely people of course)

PS  I have missed this forum and am happy to be back.

[Salina]

I wear both.   I wear mens clothes when required (most of the time) but I also wear dresses, skirts and lingerie when I can.  I prefer ti wear lingerie both under a nice dress  or under my mens clothes as it makes me feel more feminin and it feels natural and more comfortable.