Clothes don't 'enable' you to do anything. It just changes the way you look.
It all depends on your body type which is something you have recognised. By comparing yourself with Matador, I would imagine you are fairly well built so should do something that enhances that look.
I'm assuming you are from the USA, as most people here are. Most of the links I'll provide are American, or have American counterparts so should be easily found.
http://www.topman.com/webapp/wcs/stores ... &langId=-1
I've seen Matador wear something similar on The Pick Up Artist show, combined with dog tags or other necklaces.
Depends on your comfort zones also. I'd consider going to a more upmarket store (I don't know any American equivalents but something like Selfridges in the UK) or somewhere where they may offer a personal shopper and say "I want a new, more outgoing look" and maybe show them a picture of Matador, or Simeon (I remember he had a fairly similar style, despite being less well built).
Hope it helps,
Dro
--Edit--
Just stumbled across this site and it looks choc-a-bloc full of good, fairly unique clothes.
http://www.80spurple.com/