I own a number of watches, but I prefer my Rolex watches over the others as far as wrist time goes. My Sub is extremely versatile with a nato strap, rubber strap and oyster bracelet.
I wear my '73 1655 Explorer II for special occasions. A gift from my dad for graduating. (long before the price skyrocketed

) He paid 900 dollars for it in 1981, the year I was born.
And for what it's worth, I don't see Rolex as being a high end timepiece company. (L&S, AP, PP, etc) I see them as a world class marketing firm, who has always stuck by classic, timeless designs when other companies have shifted. (speaking to Omega discontinuing the sword hand Seamaster, and jumbo case sizes, etc)
It's not a status symbol to me. It's a watch. 80% of the time it's tucked under my sleeve in case I need to know what time it is. Let us not forget that 2 ct. diamond engagement rings, tennis bracelets, large gold and platinum rings that people wear on a daily basis. Are they pretentious as well? At very least my jewelry serves a purpose.