When I was 14 and living in a small town in England, I discovered the menswear inspired look via the Sloanes (which the Free Dictionary defines as "young upper-class or upper-middle-class women, having a home in London and in the country, characterized typically as wearing expensive informal country clothes"). Though I didn't relate to the lifestyle, I loved the look and adopted it with ease -- rolled-up jeans, doc martens, and a basic tee with either a tweed waistcoat or jacket over it. I still remember my dismay when I took home a gorgeous tweed jacket I had purchased in Covent Garden only to discover that it reeked of its former owner and had to be trashed. Beware of outdoor markets! Though I've expanded my wardrobe throughout the years, I've never abandoned the basics of the menswear look. Adding an ultra-feminine piece like chunky jewelry or strappy shoes keeps it from veering into Annie Hall territory.
Images: 1) Stylebop. 2) Boden. 3) Jason Wu. 4 & 5) Carrier Company. 6) L.L.Bean. 7) The Sartorialist.