pennyT wrote:From experience...
In general if you are dressing up to go out into the real world, dressing close to your age is best. If you dress sexy but close to your age few people really pay attention to you and you can pass much easier going shopping, to the mall or the grocery store or out to dinner in a restaurant.
Of course if you just want to attract the boys for "discreet activities" then by all means dress slutty... boys don't care about dressing your age! Show lots of nylon clad leg!
giggles...
pennyt
That is a very good point. When I first started dressing, it was a fantasy. I'd buy totally impractical, inappropriate clothing... even though I was dressing close to my age, I still looked like a guy wearing women's clothes.
These days I dress to pass, which is a completely different thing. I keep an eye on what women my age wear as well as their hair and make-up. Most of my outfits are day-to-day stuff: casual slacks & jeans (usually flared), blouses and sweaters. It's actually very rare for a woman these days to wear skirts, other than dressing up for a night out, or more formal occasions.
There are a few rules I have to stick to in order to pass well. I have to de-emphasize my shoulders, which while not huge, are wider than I'd really like. A dark top with a lighter skirt or pants tends to help this, as do flaring or puffed skirts (luckily these have been in fashion recently, and I can just about get away with the style, which would otherwise be a bit young for me). I can't really wear sleeveless tops as they make my shoulders stand out. This makes it hard to find a fancy dress as most are sleeveless and/or backless, but I've worn them with cropped jackets or little bolero sweaters which works for me.
The best bet is to do what women do... find a good feature and draw attention to it. I'm lucky enough to have a narrow waist, so clingy tops, corsets ( yum :D ), wide belts, and high-waisted pants & skirts all help show it off.
Oh, and if you are going out any time other than summer, get a nice coat and accessories (scarves, gloves, hats etc.) Women rarely go without them. And don't forget a good handbag!