Rebellious teen Holden would definitely be rocking some leather in the 21st century

in Fiction by

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

Rachel Carter grew up surrounded by trees and snow and mountains. She graduated from the University of Vermont and Columbia University, where she received her MFA in nonfiction writing. She is the author of the So Close to You series with Harperteen. These days you can find her working on her next novel in the woods of Vermont.

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