It sounds like you had a good time, and it is great that you have an understanding friend.
QuoteI've always found it hard to buy girls' clothing, seeing as I live in a town where it is frowned upon by most of the population.
Really? How on earth do girls go shopping then, with all that frowning going on? What do husbands and boyfriends do when they want to buy their wives / girlfriends something nice?
Going into a shop and buying girls clothing is only a problem because you know who it is for, and therefore believe that everyone else will know too. But, unless you live in a town straight out of a Stephen King novel where telepathy is rife, how can they?
In all honesty, I used to feel the same way. I used to think that if I walked into a shop and bought female clothing that the assistants would all be laughing at me, and somebody would point and say "Hey everyone, look at that weirdo... he wants to be a girl!"
That lasted until one day I saw a jumper that I just knew my girlfriend at the time would love. I walked into the shop, and looked at them more closely, and not one person paid me any attention. I picked out her size, and on the way to the checkout saw a few things that appealed to me, so I stopped and looked at them. No one cared - I was just another person browsing through the shop. I went to the checkout, and the girl there reacted completely normally, took payment and thanked me. I walked out, without being subjected to suspicion, ridicule or humiliation.
The point is, a shop exists to sell things. They get short customers, tall customers, fat customers, thin customers, male customers and female customers. If you walk in looking nervous and furtive you will attract attention - probably from a security guard thinking you are a potential shoplifter! If you just walk in, browse and purchase whatever takes your fancy then no one pays you the slightest bit of attention over and above the norm.
I know it's a big hurdle to overcome, but I would urge anyone living in fear of going clothes shopping to give it a go - it really is easy to do, but that confidence can only be gained by doing it. The only thing stopping you is yourself.
Failing which, Ebay is a good option too with some great bargains if you hunt around hard enough... and not a shop assistant in sight