Will it be worth buying 1 expensive watch such as Omega, or Cartier for 1500-2000? My other option is to buy 2 or 3 watches for under 1000. From such places as Hugo Boss, GUESS etc. Currently I already have 2 inexpensive watches 200-350 that are really nice but seem to wear fast. ( I do wear them all the time). My only thinking is that if I buy a more expensive watch it won't look worn out as fast and last me way longer. Is it worth going up in price when I could be getting a few cool watches for much cheaper. I'm not sure the average eye would know the difference between the two. Get the Omega or Cartier. Boss, Guess and those fashion watches are junk and will tell people that actually look at watches that you have no sense of style.