For the average watch enthusiast, buying and selling of watches is usually at a loss. Maybe a break even at best. Most consider this simply the cost of owning the watch for the months or years they enjoy it.
Do not be confused or misled by statements that certain watches have a 'higher resale value' than others. Since almost all watches (except the truly rare and special collectibles) lose value over time, you have to judge the resale value of a watch by what you lose, not what you get back.
For example, say you have a choice between a $3500 watch that has an 80% resale value versus a $1750 watch with only a 60% resale value. The more expensive watch sounds like the better investment. But when you look at how much you will lose, the result may be surprising.
$3500 new, resell for $2800 (80%), net loss $700
$1750 new, resell for $1050 (60%), net loss $700
While these numbers are only examples, they show that you need to specifically evaluate your choices rather than simply relying on generalizations about 'better resale.' For investing and resale, used watches are often a better financial deal because they are already depreciated to the resale value--so you are much more likely to be able to resell them at close to what you paid for them.