I wear both. Depends on what I'm doing. I'm not going to mess up a good north face jacket while I'm out doing yard work. I put on the carhart stuff.
I have a macbook pro from april 2007, iphone 4 because my 3g died. I have an HP Touchpad because it's cheap. I think I have an iPod version 5.5 in the glove box of my car hooked to the stereo.
I like the 1911, but for carry, I pick a glock. When I have to use it, I won't feel as bad turning over my glock 22 for evidence as turning over a kimber custom 1911. I'm pondering getting a soviet surplus pistol for EDC just because of that. Home defense I have an AK47 -- and I trust it with my life.
For me, it comes down to being smart with money, not so much the image I portray. Another question is how many people wear a rolex vs fossil vs skagen vs breitling vs etc.