I think you have to just go with what appeals to you the most. The jubilee band seems more dressier in my opinion and the Oyster band seems more sportier. Try several on and see which watch style "pops" the most on your wrist!!! I was able to purchase both of my Rolex's from Ben Bridge and paid for it in 12 months with zero financing. Tourneau has a zero finance/credit option as well that you may want to check out.
I have a men's white faced with fluted bezel and jubilee which belonged to my dad. My dad's watch is from the 1980's - I think?
My first Rolex that I purchased was the ladies size with a fluted bezel with jubilee band and the salmon/pink face with Roman numerals. I really love the Roman numerals on a Rolex for some reason!!! And I love the salmon/pink face! Very feminine! This watch is probably 4 to 5 years old, so I have the older jubilee bracelet instead of the nicer jubilee bracelet that has the hidden clasp. I wore this watch every day until I got my 2nd Rolex, so now I just alternate Rolex watches depending on my outfit. Ironically, once I got my Rolex, I stopped wearing all of my other watches that I had in my collection (Hamilton, Seiko, Fossil, etc.) I feel guilty sometimes not wearing my other watches, but I love my Rolex so much that I just want to wear them all of the time!!
My second Rolex that I purchased is the blue-faced mid-size with smooth bezel and Oyster bracelet with Roman numerals which definitely looks sporty but I think the Roman numerals dress up the watch! I love the mid-size and I think I would buy another mid-size if I ever purchased another Rolex. This watch is only 1 years old.
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