Literary Underwear: Get In Character


literary underwear

Everyone knows the old trick. You have to give a public speech. You’re nervous. So you picture everyone in their underwear. Voila. Nerves gone. What they never talk about is the lasting effects of picturing people in their underwear. Soon enough that’s all one is doing. But it doesn’t stop there. Soon, we’re picturing movie characters in their underwear. And then singers and popstars who aren’t already in their underwear.

And then, like the twee’s we are, it’s on to literary characters. What underwear looks are our favorite literary characters wearing? We assembled a list of 15 guesses that are every bit as page-turning as the character’s themselves.

A Confederacy of Dunces by John Kennedy Toole (1980)


  • THE CHARACTER: An overweight, over-educated, New Orleans-loving buffoon
  •  THE UNDERWEAR: Charlie Dog Bruce Boxer
  • THE REASON: In an attempt to relate to the most common of great men, this unaware elitist would wear the most simple pair of boxer shorts imaginable (and probably hide a couple extra hot dogs down there too).


Great Expectations by Charles Dickens (1860)


  • THE CHARACTER: A romantic lad with a big heart and a thirst for experience that brings that make him mature.
  •  THE UNDERWEAR: Wood Briefs
  • THE REASON: Pip may be a great many things, but being flamboyant is not one of them.


The Big Sleep by Raymond Chandler (1939) & The Maltese Falcom by Dashiell Hammett (1930)


  • THE CHARACTER(S): Two hard-nosed private dicks.
  •  THE UNDERWEAR: Mack Weldon 5X5 Brief Pack.
  • THE REASON: “She wasn’t just a lousy secretary, she also forgot to wash my briefs, so I need 5 to make it through the week … but she makes one hell of a cup of coffee.”


Dracula by Bram Stoker (1897)


  • THE CHARACTER: Let’s just say he’s a lot like Gary Oldman.
  •  THE UNDERWEAR: Good Devil Rotica Sheer Cheeky Brief in black and red
  • THE REASON: Do we have to spell it out for you?

Anna Karenina by Leo Tolstoy (1877)


  • THE CHARACTER: The princely brother of Anna Karenina. He’s a philanderer, rastabout, party animal, and bon vivant.
  •  THE UNDERWEAR: The Andrew Christian Trophy Boy Spider Thong with Show-It Tech
  • THE REASON: Philanderer … rastabout … bon vivant … Show-It Tech. Yeah, totally.


Gone With The Wind by Margaret Mitchel (1936)


  • THE CHARACTER: A cynical and charming rogue who is much more than the public persona he potrays.
  •  THE UNDERWEAR: Tani Everyday Silk Touch
  • THE REASON: Frankly, he only gives a damn about comfortable underwear.


Moby Dick by Herman Melville (1851)


  • THE CHARACTER: The enigmatic narrator of the great white whale tale.
  •  THE UNDERWEAR: The aussieBum WrestleMe USA Full Body Trunk
  • THE REASON: Imagine him, up on the mast, harpoon in hand, water cresting the boat as the mighty beast and Ahab dance their final pass. Do you think normal trunks would be warm enough? Of course not.


The Great Gatsby by F. Scott Fitzgerald (1925)


  • THE CHARACTER: The man who is everything to everyone, but not enough to the woman he loves.
  •  THE UNDERWEAR: The XVII Zephyr Men’s Briefs
  • THE REASON: The diamond-like design, the font edging of the brand name. If that isn’t the roaring twenties of underwear, we don’t know what is.

The Stranger By Albert Camus (1942)



  • THE CHARACTER: An observant man who feels particularly nothing about practically everything.
  •  THE UNDERWEAR: Bjorn Borg Basic Solids
  • THE REASON: Even in Algeria, the French wear black and white.


Doctor Zhivago By Boris Pasternak (1957)


  • THE CHARACTER: An exemplary figure, an honest man, tempted by the love of another.
  •  THE UNDERWEAR: Nasty Pig Long Underwear
  • THE REASON: Russian winter. Enough said.


Robinson Crusoe By Daniel Defoe (1719)


  • THE CHARACTER: The first shipwrecked character ever to grace book pages.
  •  THE UNDERWEAR: The Intymen Tie Me Up Swimmer
  • THE REASON: It’s a long swim back to England from the South Seas. A good suit is needed.


The Three Musketeers by Alexandre Dumas (1844)


  • THE CHARACTER(S): The three valiant saviors of the crown and French honor.
  •  THE UNDERWEAR: The Rounderbum Weekend Trunks
  • THE REASON: They were the reason we say “all good things come in threes.”


Edgar Allan Poe (b. 1809 d. 1849)


  • THE CHARACTER: Yes, we know he’s not a character. But at this point he might as well be.
  •  THE UNDERWEAR: The Gregg Homme Strip Trunks
  • THE REASON: We’d like to think he was wearing something equally macabre when he wrote The Pit And The Pendulum.


Wuthering Heights by Emily Brontë (1847)


  • THE CHARACTER: A man in love who turns vengeful and bitter as he grows old.
  •  THE UNDERWEAR: The Hardhause Flame (and Grey) Trunks.
  • THE REASON: The fire of love that once burned bright in fair Heathcliff’s heart has burnt out and left nothing but grey stone.


The Metamorphosis by Franz Kafka (1915)


  • THE CHARACTER: “When Gregor Samsa woke up one morning from unsettling dreams, he found himself changed wait into a monstrous vermin.”
  •  THE UNDERWEAR: The N2N Titan Jock
  • THE REASON: Eight legs and a thorax will require some clever snapping and adjusting.


Did we forget any great characters? Who is your favorite literary character and what underwear do you think they would wear? Let us know with a comment below or by tweeting @underwearexpert.

For more information on these brands: Charlie Dog, Wood, Mack Weldon, Gooddevil, Andrew Christian, Tani, Aussiebum, XVII, Bjorn Borg, Nasty Pig, Intymen, Rounderbum, Gregg Homme, HardHaus, N2N

Photo Credits: Charlie Dog, Wood, Mack Weldon, Gooddevil, Andrew Christian, Tani, Aussiebum, XVII, Bjorn Borg, Nasty Pig, intymen, Rounderbum, Gregg Homme, HardHause, N2N

Get The Look

Nasty Pig

Long Johns


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Everyday Silktouch Trunk


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Andrew Christian



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Gregg Homme

Strip Trunks


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Classic Brief - Forest Green


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Björn Borg

Basic Solids


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WrestleMe USA


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Charlie Dog



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Titan Jock


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Zephyr Men's Briefs


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Good Devil



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Mack Weldon

5X5 Briefs


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