To be honest I don't think you need to worry about Pimping yourself up so that you can stand out. If you have your inner game completely locked down that's all that matters, who cares what you are wearing.

I agree, wearing clothes that you feel comfortable and good in can increase your confidence. If you wear something you don't feel all that comfortable in, you will feel abit of a dick and you could come across looking abit of a dick to others. Therefore choose clothes/accessories that compliment your own personality, physique, general tastes/styles.

Have a style that is congruent to who you are and play to those strengths where you can. If you've seen season 1 of the 'pick up artist' don't go down the route that guy Fred did, being 45 and feeling he needed to dress younger he just ended up looking like abit of a clown. Pick a style that is you i.e. 'Retro' nobody else but your own.

And to answer your question about hats, I think trilbys are pretty cool I have one and I like to sport it every now and then.

Lock in props; I'm not too sure to be honest. If you feel you could pull off a feather boa outside of canal street then go for it!! but to be honest mate, correct me if im wrong but I don't think thats you.