Bell & Ross WWII Bomber Regulator Heritage

This oversized Swiss-made timepiece first caught our eye at Baselworld 2012 and we've been obsessing over it ever since. Browse through Bell & Ross literature and you'll quickly learn that the deep notches made it easy for WWII pilots to spin the bezel during flights. That's great, but unless you're dressing like Private Ryan this Halloween, you'll need a better reason to drop a mortgage payment on a new companion for your right wrist.

If you're ready to make the jump, consider yourself forewarned: This is a big watch for big personalities. The face is nearly two inches across – one and a quarter is standard – so let this be the statement-making component of your outfit (save the green pants for another day). Consider the size, then the olive-colored calfskin strap, and you'll soon understand why this isn't a watch for the office (stick with a muted, minimalist watch from 9–5). But come quitting time, pair this with jeans and a blazer for date night, or khakis and a T-shirt for Thursday-night beers with the guys. This may have been standard issue for Grandpa the aviator, but today it's a fashion-first accessory (and a great one at that). [$6,600; bellross.com]