The Only Way To Wear A Button-Down With Style, 1966

The San Francisco Chronicle recently chose a very intersting piece to run from its archives. The paper chose a 50-year-old piece brimming with anecdotes about the buttondown collar.

It opens like this:

The late Jack Kennedy looked up from his desk in the White House on a day in 1963. One of his aides had come in to confer with him. The aide was wearing a white Brooks Brothers button-down shirt.

The President was pained, visibly. “For heaven’s sake,” he told the puzzled chap. Take off that shirt. Nobody wears those things anymore except Chester Bowles and Adlai.”

The author goes on to praise the virtues of the frayed collar:

The only way to wear a button-down with any style at all these days is to follow the example of Mr. George Draper of The Chron. I am convinced that he has an army of galley slaves who wear his blue shirts until they are deliciously frayed. Then George takes them on, just after the collars have been turned the second time. On him, it looks good.

There’s some literary craft in this passage:

The only people besides high Chronicle potentates who still wear the old BB number are members of the staff of Time and Life who are over 50, certain Hollywood press agents, and old ladies who stumble about Pebble Beach with double scotches in their hands, unaware they have died.

In other times, it was different: In the days before all the Irish-Catholics earning over 15 grand a year belonged to all the right country clubs, and we were properly oppressed by the Yalies and the lads from Old Nassau, the Brooks Brothers button-down was a thing, the real status symbol.

As for the rest, in fairness I’ll direct you to the Chronicle site. Today I’m in a fairly new white custom buttondown from Ratio. I’ll see if I can’t rough it up a bit. — CC

15 Comments on "The Only Way To Wear A Button-Down With Style, 1966"

  1. “and old ladies who stumble about Pebble Beach with double scotches in their hands, unaware they have died.”

    Priceless visual –

  2. Vern Trotter | December 21, 2016 at 3:29 pm |

    The trouble with wearing a shirt in this condition (pictured) is that it is one trip away from totally disintegrating at the laundry. Especially in NY.

  3. I pulled out a 5-year-old BB OCBD the other day and noticed, for the first time, that the collar is really fraying along one of the edges. In the past, that it would have meant it was time for the trash. But now that I’ve been enlightened, I know the fun is just beginning.

  4. Raymond Shaw | December 21, 2016 at 5:28 pm |

    If it was good enough for Chet and Ad it’s good enough for me. BTW, go to (if it’s still there) website Natural Shoulder which was (is) a gallery of the suits and their well-known wearers in the Fifties. A LOT of CIA boys wore buttondowns, from Old Man Dulles on down, and they were serious dudes.

  5. I’ve never been a fan of shabby chic of which the frayed collar and cracked shoe phenom seem to be. It’s a badge of honor for a certain crowd but not me. I suppose it’s because I don’t come from serious old money. ;o)

  6. Reminds me of being a little kid in the 50s: the WORST thing to go out in was a pair of new, dark, stiff blue jeans. Never any teen stigma to new shirts or shoes that I recall.

  7. Great post on shabby chic, CC. This reminds me of what Tom Wolfe called the Boston “cracked shoe” look-you know, Adlai Stevenson in his expensive dress shoes with a large hole in the sole. Kind of ironic because Boston has always had a large number of cobblers and fine clothing stores including the venerable Brooks Brothers outpost on Newbury Street. I would love to see a post on clothes that get better with age, like Barbour jackets, khakis with frayed hems, tweed jackets, and of course BB OCBDs.

  8. The Man Who Was Thursday | December 22, 2016 at 8:06 am |

    @Chris I hear you. Growing up, and coming from No Money™, I don’t subscribe to that rationale either. We always tried to hide or polish away any shabbiness and “paint on the smell of soap”.
    My OCBD’s with overly-frayed collars are typically relegated to mufti wear, and after they’re too beat for that, yard work.
    Cool article either way– it’s a nice little snapshot into opinions from a not-so-distant past that’s sadly all but forgotten.

  9. Rick Woodward | December 22, 2016 at 9:25 am |

    I lived in NYC in the late 70s and early 80s. I had a bunch of BB OCBDs, which I took to a Chinese laundry around the corner from my apartment and my best recollection is that they charged less than a dollar a shirt. Better still they would turn collars for two dollars. Not exactly a new shirt but a great deal for a young guy with serious budget issues.

  10. Haven’t clicked on the link yet but I’m going to guess that that’s a Charles McCabe column. He’s a little before my time but I recall catching him towards the end of his stint at the Chronicle, which had the finest columnists anywhere.

  11. Evan Everhart | February 12, 2018 at 2:07 pm |

    While I do have some frayed shirts that are too dear for various reasons to part with, and which I do occasionally wear, I cannot honestly say that I am a proponent or necessarily a practitioner of the whole frayed collar/cracked shoe lifestyle. I mostly wear Grandfather’s and Father’s old clothes which have by and large held up rather well. I also add in new or vintage items as needed or required, but honestly the whole cracked shoe thing offends my sensibilities. It seems rotten to not care for your shoe. It seems almost wasteful to let a good pair of shoes get to the point of no return. I still have Grandad’s and Dad’s shoes too, and they kept them up, or else I wouldn’t, ditto their suits, though Father was much worse about it than Grandfather. Good clothes warrant good care and respect. I’ve got some of Great-Grandad’s clothes too, the ones that he made, they’re fresh and sound as can be.

  12. FELIX CASTANEDA | July 18, 2018 at 7:53 pm |

    What does “turn the collar” mean?

  13. Evan Everhart | July 18, 2018 at 8:31 pm |

    Turning a collar was an old procedure, that alterations tailors and launderers used to perform (back in the days before fused interlining – which precludes any possibility of this procedure), to give new life to a shirt’s collar when its begun to fray at the edges. The collar wouls literally be unsewn and then inside-outed so that the fresh material of the inside would then be on the outside. Some particularly parsimonious individuals would even have collars cut from their shirt tails after that if the collars had already been turned.

    Entertaining addendum; there’s also a charming reference to either a thrice turned doublet or breeches in Shakespeare’s Taming of the Shrew.

  14. I’m not too fond of the frayed collar/pants look either. All clothing that has been worn and loved to death has a fixed life span. When it’s worn out (beyond turning the collar) its time to toss it into the rag bin and replace it with a similar item anew.

  15. I consider the frayed collar/cracked shoe business to be the 1960’s equivalent of today’s black tshirts and ripped jeans. And often worn by folks of similar lineage.

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