George looked exactly how I expected someone who went to Yale in the 50s to look. He wore a tie every day. Round tortoiseshell glasses perched on his aquiline nose. His voice fell somewhere on the spectrum between Franklin Roosevelt and George Plimpton. George, like many of the men in his family before him, was a Yalie; a fact he brought up on an almost hourly basis. He also often mentioned his partner, Douglas, who had passed away a decade before. One specific story revolved around George's embarrassment when Douglas, a Dartmouth student, visited him at school for the first time. Assuming George was alluding to the difficulties of introducing a boyfriend to friends in Eisenhower-era New Haven, I made some remark about how hard that must have been for him.
"It was," George responded. "He wore boots just like yours all the time." He pointed at my L.L. Bean duck boots. "You wear those things if you're going hiking in the woods. You don't wear them to walk Bucky in the city," he said, referring to the Pomeranian he paid me seven dollars an hour to walk.
I was reminded of this conversation a month as I was looking at a post on Brooks Brothers' Rogues & Gentlemen blog. Titled "Fall Essentials – Urban Woodsmen," the post featured, alongside "indispensable" prep pieces like the tweed sport coat and the "updated knitted tie, items like a vintage-looking canvas rucksack, a navy puffer vest, and Red Wing boots (which Brooks Brothers now carries). These pieces of clothing, the copy explained, are ideal for "strolling down the streets of Manhattan or chopping down trees."
The meeting of Ivy Style and rustic Americana is emblematic of the coasts moving inward to aesthetically meet in the Middle West; this is a considerable sea change for brands like Brooks Brothers. If those that historically cater to the 1% are offering styles borrowed from the 99%, what does that say about the brands' evolution? George died four years ago, but as I read that post I pictured him turning over in his grave (along with an entire generation of former Ivy Leaguers) at the very thought that one of the pillars of the traditional Ivy League look was promoting navy puffer vests and work boots, both items of clothing that wouldn't have cut the mustard for George. The generation he belonged to defined the traditional Ivy League look: custom-made suits, button-up shirts with button-down collars, ties and cuffed pants without pleats. And while we've all come to expect the woodsman look in Brooklyn (or on "Portlandia"), it's finally drifting uptown, in a metaphoric sense. It took a while, but the plaid shirts and thick woolen wears of the New England weekend meanderer and the Minneapolis logger have coalesced with the traditional urban prep look, to the point that it's getting hard to tell the two styles apart anymore.
This represents a pretty big shift for a company that in 1991 had George Plimpton write the copy for a six-page advertisement in The Atlantic. Plimpton extolled the company's "brand of elitism," and seemed shocked that Brooks Brothers had deigned to start selling blue jeans.
Brooks Brothers' most recent embrace of the urban lumberjack look—a willingness to get their hands dirty, also—highlights an enthusiasm among sartorially-minded gentlemen to embrace a more relaxed idea of what formal dress can be (the flannel shirt is fine for the office if you pair it with a knit tie and tweed sport coat), and it also shows the latest evolution of the American preppy look. Once strictly an aesthetic native to old-money New Englanders and their kids en route to prep school and East Coast colleges, now Barbour hunting jackets are as acceptable part of daily wear in fall as pastel tennis shirts are the summer. Even Gant, another brand launched out of New Haven in the late 1940s, has seen their fortunes turn around thanks to a popular partnership with designer Michael Bastian, a guy who describes his influence as "deep-woods preppy." It's a look influenced by his growing up on Lake Ontario, not time spent at Yale.
Paging through the book Ivy Style, a history of Ivy League dressing forthcoming from Yale Press, you get the feeling that the traditional preppy look hasn't really changed all that much from the look's Golden Age in the late 1950s to mid 60s. If you look at pictures of students from Yale, Harvard and Princeton from the interwar years to the early 1960s (think Fitzgerald's This Side of Paradise to Animal House's wayback style, for pop-culture points of reference) you see jackets and ties, everyday guys dressed up in a way that might mark them as a dandy today. But as America relaxed culturally in the 1960s, you began to see the ties and jackets disappear, save for the sort of students who voted for Nixon and worshipped William F. Buckley. By 1968, Yale had abolished its jacket and tie dress code that had been instituted in 1952 to combat "Disorderliness" and "Sloppiness." But even before the revolutionary days of the late '60s hit Yale, the other Ivies started to mark a decline in the suit and tie look. As Richard Press, grandson of J. Press founder Jacobi Press—the other major supplier of wears for the traditional Ivy look—told me of his days at Dartmouth in the last years of the 50s, unless you were going to a formal event, "If you dressed up with a jacket and tie you looked like a shmuck in most circumstances."
The 1970s weren't the Ivy look's best decades: long hair, beards, bellbottoms and t-shirts became commonplace. Young Republicans shopped at Brooks Brothers, Gant, Fenn-Feinstein and J. Press for their suits, penny loafers and button-down collar shirts. It wasn't until the early 80s that America at large once more warmed to the preppy look. The satirical book, The Official Preppy Handbook, was a bestseller, and the Reagan-worshipping Alex P. Keaton of the television show "Family Ties" looked snazzy in his sport coats and suspenders. Along the way, even Andy Warhol traded in his leather jacket for a coat and tie from Brooks Brothers. As the country embraced conservatism, men's style followed suit (both literally and metaphorically). After a period of slumber, the Ivy style had come roaring back—and not much had changed. Reagan promised to deliver us safely to the prosperity of the post-war years, Jerry Rubin went from yippie to yuppie, and "earthy" and "laidback" gave way to wide ties, pinstripes and shined shoes.
But while pinstripes and Ralph Lauren Polo shirts were all the rage among adults, the younger American preppy was comfortable mixing up the dressed-down look of their parents' generation, but in a clean-cut way: Ski gear was worn off the slopes, and Maine Hunting Shoes were worn on the sidewalks of big cities. In 1984, Eddie Bauer teamed with Ford to create the very popular Bronco 2 SUV. And that same year, the first suburban lumberjack heartthrob came in the form of Jake Ryan, the wealthy, plaid-shirt-wearing object of affection for Molly Ringwald's character in Sixteen Candles. Played by then-23-year-old Michael Schoeffling, Jake Ryan is essentially the patron saint of the urban lumberjack. Ryan's ensembles included Oxford shirts under sweater vests with jeans, a pair of work boots and a clean preppy haircut. Whether he knew it or not, John Hughes was doing something more than making some of the greatest teen movies ever; he was telling the world it was perfectly fine to mix preppy with workwear. Jake Ryan may not have been the first urban lumberjack on film, but he remains the greatest, as well as a counterweight to the preppy rich kids of Hughes' Pretty in Pink, Andrew McCarthy and James Spader.
The 1990s gave new meaning to the phenomenon. Pacific Northwest bands like Tad and Mudhoney wore flannel shirts and jeans. Nirvana sold millions of albums and suddenly the grunge look was seen everywhere from your local Kmart to the Perry Ellis New York Fashion Week runway, where Marc Jacobs introduced his grunge-inspired collection for spring/summer 1993 to the world. But while grunge came and went in the span of a few years, the even bigger change to American menswear during the Clinton era was the growing ascendancy of Abercrombie & Fitch in malls across America. A&F, long a sporting and hunting-supply company, underwent a total rebrand in the early 90s. No longer was it the store where Ernest Hemingway shopped to buy bullets for his rifle; now they were in the business of selling high-end and high-priced merchandise in a frattish style (or "neo-preppy" as Women's Wear Daily dubbed it ). While some may scoff at the suggestion, A&F going from hunters to frat boys was an important step in the progression of the urban woodsman.
These days, commenting on the hairy-faced gentlemen walking down the street in a major city has become passé. Yes, lots of guys have beards. Yes, you can see them all wearing black-and-red-checkered shirts as they lope along, carrying bags filled with artisanal this and that. They may look like they're coming home from a weekend hunting trip, but they're more likely on their way to their MFA program or band practice, dressed up in whatever Made in the USA gear A Continuous Lean is hyping that week. The look isn't new, but now the menswear old-boy establishment is finally getting around to embracing the scruff.
So how did these two looks become intertwined? Maybe it's a tonic for the allegedly growing American masculinity crisis. Putting on a pair of work boots to go sit in the office imparts a sense of gruff virility to the day that a normal pair of bucks don't. Wearing a Carhartt jacket over your shirt and tie is tougher and closer to the popular conception of what is macho; therefore, so is the guy wearing the getup.
Nor can the Internet's involvement be understated. Now we can easily see what everybody else is wearing. The barriers to entry when it came to style have been demolished by the egalitarian nature of the web—even if you're not at an Ivy, you can see the look online. The same goes for guys generally stuck shopping from the ivory tower. There are a thousand Tumblrs and wannabe Bill Cunninghams and Scott Schumans out there to showcase each style and how they interact and influence each other across different continents and cultures.