Hi Shannon;
Cindy is right confidence is the key. When you are out dressed, keep you head up, look people in the eyes (dont look down) act as if you own the space you are in. I love going to the Shopping malls, but as Cindy said make sure you wear comfortable shoes.
Dont but cheap shoes. My favourites are Diania Ferari as they do wider C fittings (available on line or at outlets in Australia).
One thing is you can do to help build your confidence is find a trans friendly beautician (beauty therapist) and get your nails and toenails filed, and a nice colour polished, get your eyebrows shaped and eyelashes and eyebrows tinted and get one of the beauticians to give you a makeover.
I have a monthly session with my therapist and Doctor and I go to the beautician in the morning for my nails and toenaiils and makeup session (then once every two months I also get my eyebrows and eyelashes done, as well as periodically getting my legs and bikini line waxed, as well as my arms and underams done as well (you know their is nothing worse than seeing a woman with hairy armpits) ,After my session with the beauty therapist its off to my favorite dress shops in the mall , a glass of wine and some salmon or oysters at the oyster bar at lunch and then the trip to Doctor & Therapist. Along the way I browse all the fashion places. I also make sure I have a Womens magazine to read on the tram
This"therapy and pampering" is an amazing confidence booster and sets me up for the whole week.
Although I love high heels, realistically they are only for evenings.
But I do wear open toe wedge sandals or kitten heels, always with open toe pantie hose. In Australia Vodoo do a great line of 8 denier.
Remember Head up, be safe and own your personal space.
Hugs
JudithLynn