You're overthinking it. People wear large watches because...they're fun to wear. To the extent they express "masculinity" or whatever, they do it by signaling independence and liberation from conformity to obsolete fashion rules. Of course there's no excuse for an ugly watch, large or small. I do agree it's ridiculous when people extol the historical military associations of Panerai, IWC, etc. as if they're proud to pay homage to the bad guys in WWII.