If you spend your weekdays working in the city and your weekends retreating to the outdoors — whether you're backpacking, climbing, hunting, kayaking — you need a watch that looks great but won't fall apart the first time you bash it into a rock. The Montblanc Sport DLC Chronograph Watch ($6,100) was built with durability in mind, so it's trail ready, but was designed with a masculine minimalism that suits your business casual. It's made with a hardened stainless steel case, thermally treated, and coated with black carbon, all making it much harder than the average timepiece. The screwed case back and screw-down crown make it water resistant down to 200 meters, while the luminescent hands and face make it easy to read no matter the conditions.
In case you've forgotten, at one point watches actually served a purpose beyond status symbol or menswear accessory — people actually used them to keep track of time. The Autodromo Prototipo Chronograph Watch ($625-$775) pays homage to an era when the wristwatch was a tool that made the difference between winning and losing, the era of prototype sports car racing (think 24 Hours of LeMans or Daytona). These watches feature the sorts of tools race drivers need: with subregisters on the right and left to measure seconds and hours up to 24, a tachymeter to determine average speed, and a pulsometer to calculate heart rate. Perforated watch bands, styling suggesting the curves of a race car, and color schemes commemorating motorsports legends (on the limited edition Vic Elford variant) complete the package.
While it certainly won't replace the navigation technology typical of most airplanes, the Garmin D2 Pilot Watch ($450) would definitely be a pilot's best friend in a tight spot. While it includes everything you would expect from a standard aviator watch, it also packs in all the goodies typical of a Garmin navigation device. Its features include the ability to load in a flight plan and view it on a small map on the watch face, as well as an NRST button that will guide you to the nearest airport in case the worst happens. In addition, the watch includes a compass, horizontal situation indicator, ground speed indicator, and an altimeter.