In my journey to become more feminine (like I used to be), I've slowly started wearing makeup and dresses to work, and started phasing out my jeans and sneakers. It does make me feel prettier and more feminine, but I'm still having trouble with heels. I'm 5'8" and 170, which I know isn't huge, but I've spent half my life being taller and fatter than 90% of the men around me. Once the jokes started -- around 15 -- I stopped wearing heels and it's really hard to start wearing them again.

First, I feel uncomfortable in them (not physically) because I feel like heels are for pretty, skinny, dainty women and I'm not that. Second, I feel like I'll be judged at work, because none of the women in my office wear heels, dresses or visible makeup, and they're used to seeing me dress the same way. I don't want to get the "Oooh you look nice -- where are you off to tonight?" questions I sometimes get when I wear nice dresses. Because usually I'm not going anywhere.

Has anyone successfully added heels to their wardrobe? Any tips on not feeling like an impostor in a costume?