The Internet is full of cool places like Cool Site of the Day and Engines that aggregate cool like Daily Candy. Cool can also can be found on the library shelf. Any up and coming hipster worth his coolness can turn to the pages of the book Birth of the Cool: California Art, Design, and Culture at Midcentury [2]To examine his roots.

In the book author Elizabeth Armstrong collects contributions and explores the beginnings of Fifties modernist influences on the West Coast in art, music, film, and architecture. A pretty nifty trick.
Besides being an aesthetic and an artifact of culture, individuals and music can also embody cool and nothing is cooler than Jazz and nobody is cooler than Miles Davis. Davis' legendary album Birth Of The Cool [3]was released by Capitol Records in 1957 with music from 3 recording sessions and the album is timeless cool and even inspired a whole school of jazz musicians in California known as the "cool school.
Objects, movies, and fashion can be cool. Take Ray Ban Wayfarers, Messenger bags, Cloverfield, and other stuff. This type of cool often translates into marketing strategies targeted at the teensy segment of the culture and can lead to consumerism and the rise of materialism to enhance prestige and status based on affluence. And that's not cool!
Links:
[1] http://bp0.blogger.com/_nvjvKkd-RB4/R7MLsmJ5M2I/AAAAAAAAByY/bxIIgmyrImw/s1600-h/Miles-Davis-Cool--Collected-366906.jpg
[2] http://www.amazon.com/gp/product/3791338781/ref=cm_cr_pr_product_top
[3] http://bp1.blogger.com/_nvjvKkd-RB4/R7MK82J5M1I/AAAAAAAAByQ/s6F-vdZ3VK8/s1600-h/cool.jpg
[4] http://bp3.blogger.com/_nvjvKkd-RB4/R7MM7WJ5M4I/AAAAAAAAByo/7egk5c90440/s1600-h/poster1.jpg