Watch newbie here who wouldn't have even considered this question until about 2 months ago.
Just got a new charcoal suit and wonder which is my best choice from my limited (at this point) collection. I know now that an IWC Portugese would be best! Maybe next year.
So my choices are:
An old Citizen with gold (color) and band
New Tissot PR100 with steel bracelet and blue face
A fashion watch from 10 years ago "Prince - Paris" small case (maybe 35mm) with black face and black leather band.
Pics of the first two: