In the short term if buying at full retail yes there will be a loss.
However lets look at the progression of probably one of the most iconic, Rolex watches. The Submariner with a date. The 16610 for example.

This watch retailed for $2,250 in 1990
Today one can expect to pay $4,750-$5,500 for that same watch purchased in 1990 based on condition. Even if you wore the heck out if and was beaten up, you should still fetch at least $4,500. Five years ago, I would expect to fetch $4000 and five years prior to that approximately $3500

That being said. This really only applies to Men's Rolex watches. Ladies watches are very difficult to move. The 26mm Datejusts and Oyster Perpetuals fell off the map about a year ago. Even the solid gold ladies presidents are fetching only 3-3500 if you are lucky for 90's models.