Richard Mille RM 11

If the Richard Mille RM 11 were a movie character, it'd be the suave secret agent who's also a part-time luxury yacht salesman. In the 'Greatest Men's Luxury Watches of All Time' league, this watch throws punches with its bold, brash design that screams 'My other car’s a fighter jet.' Fans love it, haters can’t understand why you’d mortgage a house for it, and every time someone flashes one, it’s like they’re announcing they've just landed on the Forbes list. It’s not just a watch; it's a flex, an investment piece, and a half-hearted retirement plan all rolled into one.