and it wasn't nearly as bad as I thought it would be. I was planning on waiting until next week, but I saw a thrift store I had forgotten about today. So I went after work and got a floral print blue and green skirt and a lime green v neck t shirt. the top is probably too small, but the skirt might be fine. I told the woman working there that I was looking for something for a friend. Once I told her the size she kept referring to that friend as "they" even though I kept saying "she" and gave me a funny look. I think she knew I was going to wear the clothes, but didn't really say anything. hopefully I'll get to wear them after they finish in the wash and I can do it safely.
I was really anxious about buying women's clothes in public. I kept thinking about things that could go wrong when I decided that I wanted to do it. I wasn't going to do it in my home town, but I did it and it went about as smoothly as I could have hoped for shopping for women's clothes alone for the first time.

today went really well, it was a good experience.

Congrats. It's amazing how that feels accomplishing shopping in public for clothes that match our gender expression. Hugs
Mariah

Yay! I'm so happy for you and I'm sure you'll feel wonderful when you put it on!  Next time you want to buy something but you feel like you're going to have a heart attack you could also consider self check out at places like Walmart. For me, it alleviates some of the anxiety and walmart actually has a decent selection of cute clothes, accessories and makeup. I hope you enjoy your new outfit!

-Ondi

So... I'm perpetually impulsive, so I keep accidentally outing myself and being surprised that it goes okay.  Read this through the lens of "this person is perpetually impulsive and may give bad advice."

Consider the fact that you've outed yourself to that store clerk.  She gave you a funny look.  She knew she was looking at your friend.  She still helped you, she still sold you the skirt, and I'm guessing that she was polite and helpful by the fact that you describe it as a positive experience.  If my experience is a guide (see warning above), she'll be perfectly reasonable if you want to use a change room to make sure things fit next time.  And don't worry about the other people in the store.  I always pretend that they know and disapprove of what I'm up to.  Then, the only surprises are nice ones.

Back when I was presenting male my experiences in thrift stores were generally positive ones; I know that I wasn't the first male that they had ever seen buying women's clothes so that made it a bit easier. The cashier even went on and on about some shoes I was buying one time - i'm sure that my face was getting redder by the minute as she spoke and when she was done I just wanted to grab my stuff and go but she wanted to bag the stuff so I had to wait even longer  but she was very nice.

Congratulations on building up your courage to go shopping! It really does get easier each time you do it