Ive noticed alot of crossdressers are not very comfortable shopping for clothes or make up in "drab". I must admit the first couple times were foriegn to me, yet very exciting! I mean guys shop for thier SO's all the time so its no big deal. Just know your size, and keep recipts. Along time ago when I was 18 I bought some dressy black low strappy sandals with some silver sequins from walmart, well with in a day or two a strap ripped and I wanted to return them. I was very nervous, and I was I a huge line with a box of womens shoes, sweating bullets.
When it was my turn I got a 16 year old dude to help me. I said "I need to return these, their defective" He said "They didnt fit ya?" in a playful manner and I said "They dont compliment my eyes." He laughed and refunded me!
Anyway, now I get what I need Just the other day I spent way too much money on all kinds of stuff,but it was fantastic fun! I bought a hip shaping under garment , Black tee shirt and some large silver hoop earrings from Target, then checked out Famous Footwear, Then went to Ross and bought some black and pink capri sweats for 8.00 bucks! Then I skipped to Payless shoes and bought some cute white/pink sandals and some sexy sunglasses.
Thats not all I also went into a local beauty boutique and bought some nails and glue. Then to walgreens where I bought body wash, hair clips, eyeliner, lipstick, lipliner, nail polish , lotion and other stuff.It was exspensive! But im A 5'11" dude and still no one cared about what I was buying.The clerk was a hispanic gangster for cryin out loud, and he was polite.
The only comments from clerks Ive recieved were positive like "somones a lucky girl!" or "You have great taste!" Or "Would you like to try them on?" which can be embarassing, but still fun!
What im saying is, dont deprive yourself the pleasure of shopping for girl stuff and definitly dont worry about what anyone will think.If your worried about seeing someone you know, go to the department stores on the other side of town, or say your shopping for your Mom/girfriend/wife!