Last week we designed looks for classic-novel heroines, and now it’s time to dress the men. Find out what Holden Caulfield might wear as he wanders a 21st century New York, or what social-climbing Pip would put on before visiting Mrs. Havisham in her dilapidated mansion. These four men are definitely well-dressed, and—for some reason—considerably hotter when you picture them in modern clothes.

First, the covers to get you in the mood.

Book cover 1 Book covers 2

And on to our dapper heroes!

Great ExpectationsPip


Great Expectations

A modern day Pip would be a little bit trendy and a little bit classic. His roots wouldn’t necessarily reflect who he has become, but his look would always have a touch of this-guy-is-trying-too-hard. Still, he’d definitely gain Miss Havisham’s approval in this outfit…and Estella probably wouldn’t kick him out of bed for eating crackers.


Anne of Green GablesGilbert Blythe

Anne of Green Gables - Gilbert

Is there anyone swoonier than Gilbert? (The answer is no.) This outfit would perfectly capture his school-boy charm—lots of swagger, a few elegant touches, and an adorable hat. Plus he lives in Canada so he has to wear some flannel. It’s practically the law.


The Great GatsbyJay Gatsby

The Great Gatsby - Jay Gatsby

We’ve already outfitted the Gatsby-girl, and it seemed a shame to overlook the man himself. A modern Jay Gatsby would have a really nice suit. That’s a given. Plus all of his accessories would be expensive, flashy, and most likely dipped in gold. Gatsby wouldn’t be a subtle dresser, but boy would he look good.


The Catcher in the RyeHolden Caulfield

The Catcher in the Rye - Holden Caulfield

Rebellious teen Holden would definitely be rocking some leather. Plus he’d probably hold onto his prep-school tie (for the irony), and a great backpack (for convenience—he’s basically a nomad). And let’s be honest: if there was ever a literary character destined for Chuck Taylors, it’s this guy.

Who are your favorite well-dressed men in literature? Let us know in the comments!

Image Credits:

Pip: Great Expectations by rachelcarterya featuring chronograph watches

Gilbert Blythe: Anne of Green Gables – Gilbert by rachelcarterya featuring leather booties

Jay Gatsby: The Great Gatsby – Jay Gatsby by rachelcarterya featuring Tom Ford

Holden Caulfield: The Catcher in the Rye – Holden Caulfield by rachelcarterya featuring Superdry