A couple of months ago I was trying to find a cheap hair trim that wasn't going to be *too* cheap (I have long hair, so I don't trust a barber/mens' hair cutting place/discount clipper.)
I found out that JCpennys actually has a salon. And I went there, and they were the cheapest I'd seen for an actual salon. I was floored because I had no idea they existed. And the woman at the counter said that everybody says that... (ADVERTISE, argh, I hate corporate.)
Anyway, I expected them to be my reservation. I was there with no bra, no purse, I had just been lasered and electroed so my face looked like complete ->-bleeped-<- so I was going to come back later. "Oh no you can walk right in. Let me see if he has time. DO you have time to cut a lady's hair?"
Oh crap

No way I was going to out myself at that point, so i filled out stuff female and got a wonderful experience, and I'll definitely go back for my next cuts. They gave me a complimentary compact for my first visit (and I didn't have one yet, so...!!!!) and when I asked her for a bag for everything she said "That's what happens when you don't carry a purse!"
Point taken.

Because of damage in my thighs from tight pants and cramming my pockets full of junk because I didn't have a purse, I can't carry anything in my pockets at all. So even at school I started carrying my 'purse' (which is technically a travel bag.) I've gotten questioned by guys in my classes about it and I told the truth - it really was medically necessary for me. and I also told them that it's so much more convenient to whip out paper towels, wet naps, hand cleaner, my next dose of HRT, change, headphones, my GID letter, etc (well I didn't tell them the entire list) when I need it than to try to make do with a tiny wallet and a pocket or three. Frankly I think men are bleeding stupid for not carrying purses. Hurrr girls have so much crap they lug around... and it's awesome. I'm like batman. I want a bigger purse.
And you probably stand out more as a woman without a bag than with one. Earrings, makeup, a bag, and other female quantifiers are used to identify you when people can't tell or it's borderline. My bag is unisex, but seeing a guy with a mini travel bag is so rare that it's assumed a purse. High ponytail or an updo, hoop earrings (studs are unisex though usually crystal or black for men) and other touches are things that men *can* techically do but push us over the edge. Whereas they are things that people who know me as a guy don't usually think are too outrageous, at least to confront me about for the most part.
I am personally still afraid of going out in a spaghetti strap/cami or a skirt/shorts. If I get clocked in a button down shirt and jeans or slacks or a tank top or t shirt or whatever, it's not the same in my head as being outed as a 'man in a dress' or skirt or whatever. I need to get some winter/fall skirts and get over it, though. How the hell do you coordinate shoes with skirts!? Argh.