For a wedding you should wear something like a PAM187 or PAM194, Omega Railmaster XXL, a U-Boat, Breitling Avenger Seawolf, Corum Bubble, or especially something like a Graham Chronofighter - that crown guard is lovely.
For the casual occasion, such as a pick-up basketball game, I'd recommend a Patek Philippe Calatrava, or an AP Royal Oak. Perhaps an A & L would be appropriate too.
Hope that helps everyone!