use of hyphens in a compound adjective
Solution 1:
NR - it would be helpful if you could post the link to the article you are referring to. I am looking at the US version of the article, published May 13 entitled "Nicole Sturgeon, Cloaked in a New Mantle of Power".
In the retail and style industries, the term 'pencil skirt' is generally never hyphenated. However, the initial outfit being described in this article is, in fact, a dress. This is why 'pencil-skirt' is hyphenated the first time it is used in the article; the author is describing a pencil-skirt dress.
As Fashion Director of the New York Times, and I might add a phenomenal writer, I'm going to guess that when Vanessa Friedman originally penned her article, she punctuated her (arguably nasty) zinger correctly:
Put simply: written one pencil skirt, three-quarter-sleeved jacket suit critique, written 'em all.
It is possible that the style editor of the International NYT, or some other editor, or perhaps Friedman herself, inserted the unnecessary hyphen. The editor may have seen the words hyphenated when describing the pencil-skirt dress and thought the hyphen needed to stay in the zinger, for symmetry's sake... and she may also have hoped to improve the readability of said zinger.
The style of skirt is pencil; the style of jacket is three-quarter-sleeved. I hope this is helpful.
Solution 2:
The author's wording,
Put simply: written one pencil-skirt, three-quarter-sleeved jacket suit critique, written ’em all.
is just a highly compressed way of saying this:
To put it simply, if you've written one critique of a suit consisting of a pencil skirt and a three-quarter-sleeve jacket, you've written them all.
In other words, there is nothing more to be said about such suits than can be (and is) said the first time around by anyone writing about them.
The form of the original wording here plays on a phrase made famous in 1968 by Republican vice-presidential candidate Spiro Agnew (Richard Nixon's running mate), when he was asked whether he planned to visit a black ghetto (South Bronx in New York City, according to one account), during the presidential campaign:
"If you've seen one slum, you've seen them all."
A Google Books search for "if you've seen one X, you've seen them all" turns up no instances of the phrase earlier than Agnew's, so popular association of the expression with him has some validity.
If I were punctuating the original wording, I would include a hyphen between sleeved and jacket specifically to help readers recognize that the skirt and the jacket are the two main complementary pieces of the suit that is being critiqued:
Put simply: written one pencil-skirt, three-quarter-sleeved-jacket suit critique, written ’em all.
But as John Lawler notes in a series of comments above, there is no consensus among style guides as to the correct way to handle hyphenation in such compound phrases.