Man oh man - very, very late comer here to comment on a "resolved" issue, so my points may be utterly moot.
My transition from wearing almost entirely covered heels to openly wearing them public was a challenge. Taking inspiration from others in this group, I eventually realized that "if they can do it, so can I," and I did. And since that time, I have not looked back or ever regretted my decision to wear heels out if public. This is not to say that it has always been a smooth road as it hasn't. There have been times of doubt and lacking confidence in new and uncertain circumstances. I have come to learn that the best way to approach this is as other have wrote - having confidence. These are some points I have learned:
1. Select footwear for comfort and occasion. Speaking only for myself, I wear very low heels to work and never, never, never "club heels" to the office. OTK boots will be paired with an appropriate length and styled skirt.
2. Pay attention to grooming. When I am out in heels, I am always well groomed - clean shaven, hair combed, fingernails "cleaned-up," etc. Keep your feet in good shape! Some heels are only designed to be worn for very brief periods of time. Thus, I always have a pair of flats or "street style" trainers nearby should my feet start to scream, "Get us out of here!" When I wear capris, the lower part of my legs are shaved.
3. If this anyone's "Thing," wear clothing and accessories that makes you comfortable as comfort exudes confidence. There are days/times/places where wearing a pair of heels just does not "feel right" for whatever reason. When those occur, as much as I may want to wear heels, I don't. Likewise, some days it might be all feminine clothing but other days it will be a mixture.
4. Be yourself! When you should find a style you like, go with it. I have found both heels and clothing that I love and have started to put my own style together. It took some work to get there such as quite a bit of weight loss, but I am there and I love how it looks.
5. Work towards an event for which you want to wear heels. My wedding anniversary is the most important day of the year, and my wife and I always celebrate it in high style. This year I have a leather skirt for the day (at the very end of October) and although it fits fairly well, I have to lose a few more pounds to make it fit "just right." I have idea of the boots I want to wear with the skirt thus, this gives an incentive to make sure I get there.
So there you have it!