although I occassionally get lazy and wear one two days in a row.
Craig
...I generally wear whatever watch I've chosen for that week. My favorite watch to wear on the weekends is my Seiko 5.
Cheers,
Daos
... How i choose them, the budget for them, what i wear, when i wear, for which event i wear it. I decided it was best not to impose myself a discipline. I tried to in the beginning, so i get a maximum wrist time for each watch. Problem is i wasn't getting maximum pleasure that way. So whatever makes me happy on the spot, i go for it... follow ur heart 
and keep two complicated-to-set watches on the winder.
Best
Andreas
Hi gazoz,
interesting question of you which resulted in some interesting answers as well.
I wear my watches in no regular pattern, but depending on my daily schedule:
if I´m at work which means gloves, desinfectant use, possibilty to hit something I use a "daily beater" with a nylon strap, on night shifts a well readible watch.
If I´m off work, it again depends on what I´m up to: sports, music, theatre, being out with friends.
On the more social occassions (like some forumners mentioned before) I try to match my watch with my clothing in style and colour.
Best regards,
anaesdoc
This the watch I currently wear, so you may guess where I am right now

Warmer colors with colored metals, cooler colors with white metals.....If I just bought a new (or Vintage) watch than I will most definately wear it for the week or maybe longer.
Often I wear a watch during the week, and change (according to activity or going out) on the weekends.
But I have also had a long time that I have mainly been using my daily beater, a few years old Turn-O-Graph with white dial. A sporty watch without overdoing it....Can do with suit or jeans.
When I travel, I try to either wear a GMT or 2 watches..
I dont use watch winders, as I tend to have many watches in my safe or at the bank (in the safe here).. Also, I mainly prefer watches with easy uncomplicated dials (aka, no perpetuals yet, though a PP or a IWC DaVinci would interest me..)
Best regards
Hans
P.S. Great idea with many great comments