One of the New York Times most popular articles this week centered around a trove of letters written over several years by a young Hillary Rodham to a friend she met in high school, now a professor in California. The Times sums up the discovery of the letters thusly:
"Ms. Rodham's 30 dispatches are by turns angst-ridden and prosaic, glib and brooding, anguished and ebullient -- a rare unfiltered look into the head and heart of a future first lady and senator and would-be president."
Of more interest to us, however, is the 1969 photo that accompanied the article. Is this look evidence of a major lapse in sartorial judgment, or was Clinton -- as with her 2002 vote to authorize the use of force in Iraq -- just kind of going along with what everyone else was doing at the time? In short, is this outfit a mistake...or a "regret?"
And, like Iraq, the closer you look, the worse things get...
It's time to step back and get some perspective.The radical social and political experimentation of the late 60s and early 70s were reflected in the era's clothing, but where did Hillary Rodham fall on the fashion spectrum? Was she considered sexy-librarian-ish? Pretty-elegant? Asexually cute?
"Just How Big A Dork Was Hillary Clinton Anyway?"
Let's investigate...
The Blouse A high-collared white shirt with slightly puffed wrists and double-button cuffs, similar to what America's most mainstream apparel outlet, Sears, was selling in that year's catalog:
The Sears blouse may have been a bit too Romantic for young Hillary Rodham - she was born in Illinois to a Methodist Republican family. Her blouse is ruffle-free, and you can bet there's a neutral-toned bra under there.
The Glasses Today's "Female-Version-Of-Dwight-from-'The Office'" was 1969's "John Lennon on the Cover of 'LOOK'":
The Shoes
Shocking to the contemporary palette as these boats may be, they were fairly standard for the time: 
They're hippieish, but appear to have been color-coordinated, Virgo-style, with the pants (an upscale, more bougie choice.) They're not as blandly orthopedic-looking as the youth footwear of the time, Earth Shoes:
Nor are they as offensive as their contemporary fashion analog: the Birkenstock sandal, which is worn almost exclusively by grubby millionaires (Silicon Valley residents, Olsen twins):
Now About Those Pants
Anyone sporting these today would be larping (live-action role-playing), but remember that the late 1960s were a different time.In fact, the stiff-looking, blocky, aggressively pleated plaid pants on the right of the Sears catalog photo make Hillary's slim-fitting, tapered Op-Art pants look whimsical, even fashion-forward by comparison.
n.B.: The patterned seams create a pleasing "starburst" effect around the crotch (or "Clinton-getter"), making them, indeed, a historically significant choice.