I look at it like this and I may be different.
I would buy a $15.00 Timex and wear it if I liked the way it looked. Look at all the Seiko, Movado, Bulova, ESQ, ect.(basicly your $200-$300 watches) you want and after a while they all look the same.
Then look at a DeWitt, FM, Hublots, etc. they are unique and original designs that set them apart. While I am not about to dump $10K+ for an original looking watch I would have no reservation about spending $200-$300 for the looks. Much like the guys that build the replica Shelby Cobras, you know they are just replicas so to speak, but you can't go to your local dealership and buy one.
My watches are what they are tools to tell time. I wear them to the gym, at work, working on the house, working on the car and they all have their scars, knicks, and scratches to show for it. Atleast I don't feel guilty about breaking a $200 watch like I would if I broke a $4000.00+ gen. I have 2 gen Gucci watches that were in the $800-$1,200 range when I bought them. In the last year I have worn one of them once. Maybe one day when I am older and slow down a bit I would consider buying a gen. knowing that it would stay nice long enough to make the initial expense worth it, but with my lifestyle now it just isn't going to happen.