I know most people may not agree with me here, but for an "entry" pair of raw denim, Levis isn't too bad. I've seen raw selvedge on sale for under 100. Granted, it's not the *best*, for your first pair it won't hurt.
If it helps, I was at Macy's today and I found some nice Timex's in a similar style to the J Crew ones. I think the prices run around 40-50 bucks and they had a nice canvas strap with a vintage-esque dial.