No sixties film star would be seen without a bombshell blonde – and this watch – on the Italian coast. Named after the portside town of Portofino, this stainless-steel timepiece features classic Swiss engineering and Italian flair, thanks to its simple dial (three hands and a tiny date) and a mesh bracelet. [$4,500–$11,700; iwc.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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