I recently wrote an article at Transgender Heaven for woman who are struggling with going full time because they don't pass as well in public. The article is entitled 'How to Go Full Time When You Don't Pass'.
Much of the advice is also valid for crossdressers who are fearful of going out dressed for the first time. Though if you're not intent on transition I'd recommend you tread carefully when altering your body movements and voice. Too drastic a change could jeopardize your ability to lead a regular life when you're not en femme. You need to make sure you're okay with that.
For crossdressers, I think there are two other vital areas to be aware of if you'd like to improve your ability to pass in public.
Clothes - Wear what flatters
Now, honestly I'm the last person who should be telling you what to wear. Already your fashion proclivities are recalcitrant just by crossdressing. And you're free to wear what makes you feel most comfortable. If you'd like to improve your odds of passing, however, I recommend paying attention to what woman your age and body shape are wearing. What looks good on them? What doesn't? Use this as a basis to develop your own unique style, and do so with the confidence that you're starting from a safe, well worn style path.
Makeup - Beware the Bozo
Your goal when putting on makeup is not to hide every imperfection, nor is it to create a dramatically different image, one other than what you see in the mirror. You should approach makeup with a light touch, intent on accentuating your best features and drawing attention away from those that aren't as flattering. I recommend starting out light, with something like Bare Escentuals mineral makeup. Pay more attention to the quality of your skin - moisturize often, wear sunscreen - if you're able to get laser hair removal or electrolysis which will dramatically soften your skin. Take a look at a few more makeup tips for crossdressers here.
So go out and work your great looks, and don't worry about what others think!
What else do you do to pass as a woman in public?
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