You can see where Tom Waits' style borrows from his heroes—beatniks, jazz artists, bluesmen, folkies, and country stars. There's a timelessness in those influences that helps him look confident and effortlessly relaxed. The consistency of his style earns him credibility and a certain old-world mystique.
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 Michael Caine to Richard Gere (see full list here). Now she's guest blogging on Details.com every week. Have a hero you want to see featured? Leave a note in the comments and we'll see what we can do.