Welcome Samantha!
Thanks for visiting with us and please return often!
I suggest for figuring out what to wear in public that you pay close attention to
What women you age, size, and build typically wear, seasonally adjusted.
Know what look you prefer, and think seriously if that look would work for you in public.
Also:
Do not spend lots of money right away on clothes. Get the basics, nothing outlandish.
Try to simply look like an ordinary woman your age, not a glamorous runway model.
Go to Sephora for a makeup lesson and basic makeup. Do not buy tons, a good concealer for sure.
I suggest starting with androgynous clothes but to move to women's jeans, hiking shoes or sneakers, penny loafers, maybe a women's Polo or T shirt, and sweater. Maybe a ladies Oxford shirt. I would skip crop tops!
Undressing garments are up to you, no one can see them. But many bras are not that concealable if that is a concern. Perhaps it is easier to not see a t shirt bra than other bras.
Go slowly, move from androgynous to a slightly feminine to a more and more feminine appearance.
For a wig, if needed, go to a wig salon. They can be a big help. Buy cheaper ones first. You can order online if you prefer. Try some styles that you like. Some colors you may like but they really will not suit your complexion. Try wig styles with clothes at home before venturing out.
I also suggest contacting a transgender or specifically a cross dressing support group.
They sometimes have makeup sessions, clothing exchanges, have someone to go to stores and shop with you for female clothes and shoes, and can be otherwise helpful.
Look for many responses here from others, some may be of help for you.
Chrissy