Personally I think it's silly.
Panasonic 1993 CD player - $25
Cheapo headphones - $10
Gap Jeans bought on sale by my sister who works there - $5
Random shirt - $20
Shoes (like indestructable Merrill shoes bought on sale at Nordstrom Rack) - $40
Work cell phone that doubles as my watch - $0
Total: $100
Ok, if it's a work day, then it's a shirt ($40-100), wool slacks ($40-100), tie ($40), nice belt ($30) and a decent jacket or overcoat ($100), and good Cole Haan or Magli shoes ($100). But even all these are Neiman Marcus Last Call-type items... a good way to get that $1200 Armani jacket for $100.
In an age where I'm pretty much required to carry a cell phone at all times, I've abandoned wristwatches altogether. Once cell phones can double as decent audio players, I'll have one single electronic gadget to carry around. As a result, I don't quite understand the idea behind a $2000 wristwatch. Then again, I don't wear thick gold rings, diamond earrings or have anything pierced with 24-carat anything, so I'm definitely not in the expensive watch demographic.