[Heaven's Night]

Thats a problem if you don't have many good shops nearby, I live in a small village so used to go into the city (about half an hour on the train), which has all the shops, so that was good.
I must admit I used to be totally unsure abut going into a womens shop, it has taken me years of pushing myself to have the confidence to go in and look around, if I see something I like I will buy it with no problem at all. If I'm unsure of the size/fit and want to try it on, this is where i still struggle to some degree, it depends upon which shop it is, but I usually go and find a friendly looking assistant and ask them if it is OK to try on the clothes. Thankfully, most are very helpful, and lead me to the changing rooms and generally make sure I'm OK, however I am only confident in certain shops to do this as in some I am over conscious about what they are thinking about me!
This is where I have fallen down in the past, just like you, over thinking what others think about you. It's a weakness that I recognised years ago and actively set about to get over it. It is hard, but very doable, so please be confident with lots of positive thoughts and really try to develop that attitude I'm happy with who I am and I don't care what others think.
For me it was baby steps, just keep pushing myself little by little.
For sure compliments are fantastic and in your case are well deserved, you look brill so go with it with confidence.

I think it'll be mostly a pleasant experience when ever I pull myself together and just go.

I usually don't lack daring about this stuff, but shopping for clothes is really something that has always been awkward for me.