If your adventure doesn't require hyper-technical kicks like hard-core hiking boots or rock climbing shoes, pack just one pair of boots and carry them on your feet. It's the best way to save a space in your bag. The four rules for that pair: It needs to be tough, it needs to be comfortable at all times, it needs to function in a lot of situations, and it needs to look presentable enough to wear to a nice dinner in the city. Danner's Cloud Cap Low GTX hits all those marks. [$140; danner.com]
Mad Men's Charming Rogue
The man who played Roger Sterling, is moving on – surfing in Montauk, hanging with his son, and directing a feature film.
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