According to Sinatra.com, Ol' Blue Eyes had precise rules of style: A half-inch of a man's shirt cuffs should protrude from his jacket sleeve, trousers should fall slightly above the shoe, black is the only appropriate color to wear after dark, vests are better than cummerbunds, and you shouldn't forget to shine your shoes. In this 1962 photo, the man who knows the rules of style better than anyone pairs a fitted knit vest with his signature classic fedora.
2. Quality all-purpose fedoras can be found at J.J. Hat Center.
Even for the most skilled dressers, assembling a killer outfit sometimes requires a little more inspiration than the average online shopping experience provides. Enter Roxana Altamirano, the genius behind Nerd Boyfriend, the style blog that offers step-by-step instructions for re-creating ensembles worn by icons ranging from Ingmar Bergman to Willie Nelson. Now she's guest blogging on details.com every week. Have a hero you want to see featured? Just leave a note in the comments and we'll see what we can do.