The Outdoorsman
The Outfit: A luxury anorak with tapered seams takes the crunch out of your trail circuit and pairs well with classic mid-length Patagonia shorts. Protect soles with shoes that absorb rock shock, like the GEL-FujiRacer by Asics.

The Extras: The Suunto Ambit2 GPS watch works with thousands of apps that track your heart rate, altitude, the weather, and more.

Oakley Frogskins sunglasses ($110). Align SFT jacket by Arcteryx Veilance ($895), Outlier ultra-fine-merino tee ($98). Patagonia Gi III water shorts ($55). Kentwool Tour Profile socks ($20). Asics GEL-FujiRacer shoes ($115). Suunto Ambit2 GPS multifunction watch ($500),