I was reading StyleForum's Streetwear and Denim forum last night. What the thread was about isn't really all that important here, and I really couldn't explain it anyway (read it here if you want to try). What is important is this quote.
old school teddy boys and mods usually only had one great suit that they wore the shit out of. i admire this mentality more than the buy all you can at a cheap price mindset that a lot of modern day consumers have. high fashion isn't about making your dollar go further, it's about holding yourself to a higher regard.
Also relevant was this recent post by Giuseppe. Here is a good quote from it:
Buying things that are "pre-worn" or "distressed" is downright silly, but getting something new and wearing the hell out of it yourself over the course of many years is just the opposite, a mark of character.
I haven't been wearing quality clothing long enough to beat anything to shit, but I do have a good number of things that I am eager to beat up.
Two pairs of RRL jeans
Florsiem Kenmoor longwings
LL Bean engineer boots (coming soon)
A bunch of tweed jackets
A bunch of khakis (thinking frayed ends here)
A bunch of OCBD's (frayed cuffs and collars)
Luckily I will work in a profession where I'll be able to wear beat up stuff like this.