I'm not sure if this is the best place to post this topic - please feel free to move it somewhere more appropriate.
Basically I am looking for a little help. it may sound weird but I really want to change my clothing style to look much smarter than I do at the moment. I've just turned 30 and have spent most of my life dressing very casually - t-shirts, baggy jeans, hoodies, thick woolen jumpers etc etc.
I've always sortof fantasized about dressing a lot smarter but the desire has got a lot stronger in the last year and I've made a couple of concessions towards it. I used to refuse to wear shirts but over the last frew months I've started buying them - some plain coloured dres shirts and a couple of more casual chambray ones. I've begin wearing them but I still feel pretty self conscious around my friends or in public. I also bought a blue pinstripe suit last year with a dark blue shirt and black tie and earlier this year I put an outfit together consisting of a white shirt, black skinny tie, tweed blazer and black slim cut trousers - but I never have the opportunity really to wear these clothes. Its gotten to the stage where I get home from work, take off my casual clothes and dress in a smart outfit at home. I have even begin going to the supermarket or for walks dressed smartly (I know it sounds weird). I recently wore my tweed outfit to a wedding and my best friend (a girl) said I should dress in a suit and tie more often
My biggest problem is knowing how far to go and getting over the horrible self conscious feeling when I amdressed smartly or my total fear of dressing smartly in front my friends or family as they are really used to me never dressing up. I have also had a very bad run of luck with girlfriends in the past having always gone for casual tomboy kind of girls. Its always ended badly and I thought maybe going for a different kind of girl, someone smarter and preppier might be more of a success. I have also been growing more and more attracted to preppy-styled girls who dress smartly - I just know I have no chance getting a girl like that the way I currently dress. (Thats not the sole reason for wanting to change my style)
I was wondeirng if anyone here would be able to give me help or advice to overcome my anxiety or help me with developing my style more.