Hi Teresa,

Well fashion is a personal choice and sometimes we have to go with what makes us feel good. I tend to dress to blend in with the vanilla world and that includes a lot of jeans, tops, boots, some dresses (at the knee level) but that is me and that is what makes me feel good. It also serves the secondary purpose of not attracting too much attention. Now does this mean you have to dress dowdy? No. IMHO there is a difference between dressing "trendy" and dressing "too young". There is a point where you cannot pull off certain looks anymore regardless of your gender. If we reverse this and think about dressing as a guy . . . I could never pull off the baggy pants, boxers showing, skateboarder dude regardless of how good of shape I am in . . . it would look ridiculous for a 50 year old man to be dressed as such. Likewise, even if I passed (100 percent - not going to happen) as a woman I could never pull off some the twenty something looks (tight short skirts, crop tops, short shorts, etc.) because I would look like an older woman trying to recapture my youth. If you can live with that, then so be it and enjoy but I doubt many want to do that in public.

Now dressing "trendy" transcends age because we can all find a look which works. As a guy I tend to dress more metro when out on a date with my wife because it gives me a more youthful look without looking like a guy trying to dress young. There are plenty of great fashions for men of my age which looks fun and carefree without looking silly. Likewise when dressed as Isha, I can find plenty of "trendy" fashion tips to give a more youthful carefree vibe without looking like I am trying to recapture a lost youth. As a more mature gal, I don't feel the need to dress in skirts which go past my knees (unless I am purposely wearing a maxi dress) or apply to some unwritten rule that older women can't wear heels. I have seen plenty of very attractive older women dressed in power suits with great heels who make the look work for them. Do they look like an older women trying to look 20? No, they look like a confident woman wearing what makes her feel good.

To bottle the genie on this one. IMHO there is not right or wrong way to dress . . . it is what makes you feel good that counts. If some see it as "silly" when you are out and about but you don't care . . . then that is fine. Goodness we are men who dress in women's clothing so who are we to judge one's sense of fashion.

Hugs

Isha