For scores of eighties schoolgirls, Sixteen Candles dreamboat Jake Ryan (Michael Schoeffling) was the gold standard—a jock with a sensitive side. This ideal mixture of masculinity and endearment is also seen in his wardrobe. In perhaps his most memorable look, Jake rocks a Fair Isle knit vest with jeans and distressed work boots. The look is collegiate but not stuffy. The fit is relaxed but not sloppy. No wonder Jake Ryan is now a term used to describe the perfect boyfriend. Check out NEastStyle for more Jake Ryan looks.

Get your Fair Isle knit vest at Drake's London, Jos. A. Bank, or Rugby

Gitman Bros. Overdye Oxford Shirt in Olive or Navy

J.Crew Straight Denim in Indigo Medium Worn Wash

Chipewa Lace-up Work Boots in Dark Brown or Tan
About the author: 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.
Also on Details.com:
How to Dress Like Robert Redford
How to Dress Like Bruce Springsteen
How to Dress Like Humphrey Bogart












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