Jay Gatsby and Don Draper Are Enigmatic Bores

Notes from the fashion apocalypse.
May 8 2013 2:50 PM

The Problem With Handsome, Enigmatic Men

They’re boring.


Hang onto your scotch tumbler, Don Draper—you are about to get upstaged by the greatest stuffed shirt in American lit.

Simon Doonan Simon Doonan

Simon Doonan is an author, fashion commentator, and creative ambassador for Barneys New York.

Let me explain. Mad Men is like crack cocaine to me. Every Sunday I plonk down in front of the telly, roll down my knee-highs, grab a pig foot and a jar of pickles, and tuck into a new episode. I am not exactly sure why. Nothing much happens, and most of the characters walk around looking as if they just got bad news from the doctor. Peggy is turgid and prim, Betty a withholding bitch. Joan has lost her joie de vivre. Even Megan and jolly old Roger are in a funk. The entire dramatis personae exist in a David Lynchian stupor. And yet I am totally gripped.


These blank and tedium-drenched characters pale in comparison to the Lord King Bore himself, Don Draper. Mr. Draper is stunningly morose, bad-tempered, and humor-impaired. He is a monosyllabic, unsmiling, ungiving dude with a nasty drinking problem. A real barrel of laughs. Imagine being stuck next to him at a dinner party!

Despite his lack of pizzazz, all eyes are on Don. Why? Because he is classically handsome. He is the man in the gray flannel suit, thus giving him carte blanche to be a black hole. Think about it: Would you worship Don Draper if he resembled, say, Buddy Hackett? No. You would accost him and say, “Listen buddy [or Buddy], you are simply not handsome enough to be this dreary.”

Dapper + grumpy = compelling.

Schlumpy + grumpy = you better have some good jokes.

Which brings us to The Great Gatsby.

Jay Gatsby is the primordial muck from which all subsequent Drapers emerged. He is such a remote enigma that he makes our Don look like Rip Taylor. (I make no apologies for my habit of referencing old-school show-biz personalities. I am committed to keeping their names in the national conversation.)

So what, other than good looks, are the key components of the Gatsby/Draper paradigm?

Secrecy: Like Don, Gatsby spends much of his energy concealing a tawdry-but-sizzling back story. This is really just another way of being boring. Everyone loves a tawdry-but-sizzling back story, so what better way to torture your admirers than not to share it?

Hair: Good hair is clearly a vital asset for the successful lead bore. If Jon Hamm or Leonardo DiCaprio had hair like Marty Allen—or even Marty Feldman—that whole strong, silent shtick would seem absurd. A good head of hair is de rigueur because, while they think they act with their hearts and their minds, handsome male leads actually act with their hair. This is their instrument. (There are rare exceptions, Yul Brynner being the most noteworthy—he acted with his bald pate.)

Spiffy suits: Don and Jay are both snappy dressers. If you are going to behave in a terse, unresponsive manner, you’d better have a damn good tailor.

Gobs of dress shirts: I worked for Turnbull and Asser on Jermyn Street around the time of the 1974 Gatsby mega movie. T. and A. supplied all Robert Redford’s shirts for the famous scene where Daisy, played by Mia Farrow, weeps at the beauty of his flying garments. I vividly recall the subsequent massive uptick in the shirt biz. As sumptuous as Baz Luhrmann’s new Gatsby apparently is—I wouldn’t know since my tickets to the premier got lost in the mail—I seriously doubt this phenomenon will repeat itself. Back in 1974 that airborne abbondanza of shirts seemed like an unattainable hallucination. Now every playa from here to Fresno already has a Ralph Lauren fantasy walk-in closet.

So there it is. Sad but true, the sartorial, good-looking grumps shall inherit the Earth. I am not particularly happy about this situation. Having dedicated my life to being as folksy, bubbly, and accessible as possible, I have a strong resentment for the adoration lavished on those attractive grumpsters. I take comfort from the fact that they usually come to a horrible end. Watch out Don Draper. Better sleep with one eye open.



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