Dress shoes aren't only for work anymore. That expensive pair of black Italian oxfords you just bought? Go ahead and wear them with selvage denim and a leather jacket on Sunday, and then again on Monday with a suit and tie. And keep your socks as dark as your shoes to create a better, more slimming line. [Ermenegildo Zegna Wingtip Oxford, $675; nordstrom.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.
Plus: Greenpeace's High-Seas Avenger
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