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Polo Ralph Lauren's fall 2016 presentation. Photo: Brian Ach/Getty Images
Polo Ralph Lauren's fall 2016 presentation. Photo: Brian Ach/Getty Images

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Ralph Lauren’s American Dream

The iconic brand is struggling. How did we get here, and what happens next?

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Entering the Rhinelander Mansion on New York's Upper East Side is like quietly opening a window into Ralph Lauren's mind. Many describe Lauren's superpower as his ability to turn his wildest dreams into reality, and inside that mansion, Ralph Lauren's original flagship location, his dreams are made real in every nook and cranny of the place.

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Each room presents one lavish scene after the next, and it's not hard to imagine Lauren himself toiling at the displays to make sure everything sits just right. Spaces are small and illuminated with candles and the softest of lighting, beckoning shoppers to linger. A glass of water arrives on a small silver platter, garnished with a single slice of lemon, just for you.

It's stunningly clear here, walking slowly up a staircase lined with oil paintings from the company's collection, that Ralph Lauren is a lifestyle. No detail is left to chance: Ralph Lauren ties are fanned out on a table in front of a bar stacked high with Ralph Lauren shirts, next to a case of monogrammed Ralph Lauren cufflinks. Ralph Lauren briefcases are placed next to Ralph Lauren paperweights on a Ralph Lauren desk topped with Ralph Lauren stationery, positioned underneath a giant, glittering chandelier that can't possibly — but maybe? — be branded Ralph Lauren. Everything, right down to the 82,000 square feet of mahogany hauled in for the mansion's renovation in the 1980s, reeks of style and status and money. Old money.

Twenty blocks away, inside the Lord & Taylor on Fifth Avenue, the dream gets a little murkier. Lauren Ralph Lauren dominates one of the women's floors, and while the gold-plated signage is shiny and the tan leather couches comfy, the endless sea of khaki dresses belted at the waist are not so much impressive as they are predictable. There are no nooks nor crannies filled with odds and ends from Ralph's archives; nothing begs a pause. Jammed up in between racks of floral fit 'n' flare dresses and rows of athleisure, it's harder to see Ralph Lauren's appeal. A similar scene unfolds on the sales floor at the Herald Square Macy's, a short 10-minute walk away.

A Ralph Lauren store in Milan, Italy. Photo: Giuseppe Cacace/Getty Images

Once you leave the giant department stores of New York City and head to the malls of suburbia, Ralph Lauren becomes a few racks of Oxfords, polos, and pleated pants. Reliably found in your local Dillard's, and just as reliably found on sale.

"The clothes look good in magazines, but look older in stores," says Christina, a 31-year-old from Long Island, flipping through a rack of button-down shirts at Macy's. She likens the brand to Michael Kors — oversaturated and devalued. "I would never buy Polo at full price."

Jan Freemantle, a tourist visiting New York from Sydney, Australia, recalled how her husband used to bring her back Polo shirts picked up on business trips to California before she could find the brand in Sydney. Polo was all she knew about Ralph Lauren until recently, when on a trip to Aspen, she came across a Ralph Lauren store that carried the Purple Label and Collection lines. "It was so nice, but so expensive," she says.

Most shoppers haven't encountered the totality of Ralph Lauren's world. How could they? Since the early 2000s, Ralph Lauren Corporation has owned and operated at least 25 different brands. It's a staggering list: Polo Ralph Lauren, Polo Jeans, Polo Golf, Pink Pony, Purple Label, Blue Label, Black Label, Ralph by Ralph Lauren, Lauren Ralph Lauren, Lauren for Men, Women's Collection, RRL, RLX, Rugby, Denim & Supply, Club Monaco, Chaps, Ralph Lauren Childrenswear, Ralph Lauren Watches, Ralph Lauren Fine Jewelry, American Living, Ralph Lauren Home, Lauren Home, Ralph Lauren Paint, and Lauren Spa. Not all are still in operation.

Ralph Lauren is clearly a man who knows how to build an empire, but right now, the empire is in turmoil.

For the shoppers who actually are familiar with the company's multitude of lines, it's still exhausting. "The identity of the brand gets lost," laments Efney Hall, who has been shopping Ralph Lauren for over a decade. She likes it for its classic, elegant appeal, but she's noticed that lately, the fit of the pants has changed. She finds herself skimming over the brand's Lauren Ralph Lauren racks. She's over it.

Ralph Lauren is clearly a man who knows how to build an empire, but right now, the empire is in turmoil. Layoffs have struck the company two years in a row, eliminating 750 jobs in 2015 and another 1,000 this summer. (One former Ralph Lauren designer commented to a colleague on Instagram in June: "Glad you survived the RL Hunger Games this week!")

Lauren has stepped aside to make way for a new CEO, Stefan Larsson — the first person besides Lauren to ever hold that title in the company's 50-year history. The company has been in the process of whittling down the brand list and there are plans to refocus on just three main lines: Ralph Lauren (the new umbrella label for Women's Collection and Purple Label), Polo Ralph Lauren, and Lauren Ralph Lauren.

At the same time that Ralph Lauren is reevaluating its structure and bringing in fresh leadership, it also has to contend with the fact that the specific style of Americana that's so deeply embedded in every inch of the brand isn't something shoppers are clamoring to align themselves with now. If the privileged, preppy aesthetic that Lauren built his company around is no longer the height of aspiration, what will the future of Ralph Lauren look like?

Ralph Lauren did not grow up living the lifestyle that would later make him a billionaire. No, Ralph Lauren was born Ralph Lifshitz, a shy Jewish kid who lived in a small, two-bedroom apartment in the Bronx with his parents and three siblings. In Genuine Authentic: The Real Life of Ralph Lauren, writer Michael Gross paints a picture of young Ralph as a dreamer, never one to run with the crowd. "If white bucks were in fashion, he wore saddle shoes," a former classmate told Gross. "When we wore crew necks, he wore V-necks. He was always a step ahead."

Lauren's perception of taste and class was constructed by what he saw around him, according to Gross. His richer friends' parents drove convertibles, went on European vacations, and had country club memberships. In films, he watched Gary Cooper, Cary Grant, and Fred Astaire glide across the screen, wearing beautiful suits and getting the girls every time.

Lauren and his family at their home in East Hampton, 1977. Photo: Susan Wood/Getty Images

"I grew up playing a lot of basketball, reading, and living at the movies," Lauren said in an old interview that Gross unearthed for the book. "I guess they influenced my taste level. I liked the good things and the good life. I did not want to be a phony. I just wanted more than I had."

However, Lauren's mother had set a strict path for Ralph: he was to be a rabbi. He shuttled between secular public schools and Jewish yeshivas during his youth, eventually convincing his mother to allow him to transfer from Manhattan Talmudical Academy, where he was on the Hebrew teacher-in-training track, to DeWitt Clinton High School, an all-boys public school. In his senior yearbook, listed right below his extra-curricular participation in "Lunch Room Squad" and "Health Ed. Squad," Lauren declared what he wanted to be when he grew up: a millionaire.

At 19, he and his brother Jerry changed their last name from Lifshitz to Lauren. (As Gross reports it, Ralph polled friends on two alternatives, London or Lauren; he was personally partial to London.) In the official document filed for the name change, the reason listed was confusion over people, both at school and at work, who shared the same last name. In reality, Lifshitz had the word "shit" in it and Ralph's plans for himself did not include dealing with that for the rest of his life.

College was never a big draw for Lauren, who dropped out of the City College of New York school system after three years. He was drafted into the Army and served for two years, but the military, with all its rules and regulations, wasn't a good fit either. After the Army, he kicked off his career as a salesman, first for glove companies. Then he got into ties.

"I liked the good things and the good life. I did not want to be a phony. I just wanted more than I had."

Lauren got his first shot at professional tie design at Rivetz & Co., a high-end neckwear company. It didn't go over well. "Rivetz was a traditional firm," David Price, whose father used to own the Rivetz & Co. business, explains. "They were doing all sorts of crazy pinks and oranges and all the Ralph colors, and the industry and the customer base at Rivetz thought it was just atrocious."

But instead of backing down, Lauren went from Rivetz to Beau Brummell Cravats, where his boss, Ned Brower, let him sell his own ties — colorful, wide, and expensive — out of a drawer in the showroom. Lauren had no professional training in design, but he believed so deeply in his wild ties that other people did too. He caught the attention of Norman Hilton, one of the biggest names in the menswear industry at the time, who eventually became the first investor in Lauren's business. Polo Fashions, Inc., named after the posh sport (not the shirts Lauren would later become famous for), launched in 1968 and, as Hilton's son Nick remembers it, his father poured $75,000 into the startup. By the end of his first year running Polo Fashions, Lauren had expanded from ties into full suits that the Daily News Record (a menswear trade publication that was later folded into WWD) featured alongside heavyweights like Bill Blass and Oleg Cassini.

The company was a critical success from the beginning, although according to Nick Hilton, it was always almost bankrupt in its first few years. In 1970, Lauren won his first Coty Award (the predecessor to the CFDA Awards) for menswear, and he launched womenswear after that. In Ralph Lauren: The Man Behind the Mystique, author Jeffrey Trachtenberg describes how the move into womenswear transformed Lauren's business. It was then that he decided to change the name on his labels from Polo Fashions to Polo by Ralph Lauren, in part to imitate how other designers were using their own names on their womenswear labels. And then, for the launch of women's button-down shirts, the company added a new design element: a small embroidered polo player. It was an overnight success.

"The polo player became the new status symbol for women," Raleigh Glassberg, the buyer who purchased Ralph's first women's shirts for Bloomingdale's, told Trachtenberg. The shirts were as pricey as Lauren's ties, but it didn't matter. Everybody wanted one. As Lauren's business grew, buoyed in large part by the ‘80s prep revival, the polo player became an integral part of the women's and men's lines, including on the polo shirts that became a signature of the Ralph Lauren look.

Lauren with women wearing his designs. Photo: Kenn Bisio/Getty Images

Chaps was the first of many extensions that Ralph Lauren would experiment with. Chaps was Lauren's answer to Polo knockoffs that were flooding the market. He couldn't stop the knockoffs from being produced, so he created a cheaper line to compete with them.

The company also expanded quickly through a number of licensing partnerships, a relatively easy way to put the Ralph Lauren name on a variety of products without having to deal with manufacturing any of it.

"The bulk of the company's profits come from royalties on its extremely lucrative licensing agreements, which lend the Ralph Lauren name to manufacturers of eyewear, fragrance, furniture, and a range of apparel," the New York Times' Stephanie Strom reported in the mid-'90s. "Polo Ralph Lauren only manufactures its men's sportswear, coats, and furnishing lines; all other Ralph Lauren products, ranging from towels and sheets to shoes and sunglasses, are manufactured by others under license."

The article also noted the voracity with which Lauren launched new lines, started new partnerships, and continually built upon his vision. "The sheer number of new ideas coming out of Mr. Lauren's head at a time when the fashion industry seems to be satisfied with endlessly regurgitating old looks gives him an edge," Strom writes. "In the last year alone, he has started RRL, Polo Sport, a line of Polo Sport skin treatments, and the Ralph label."

As Lauren's empire grew, the accolades kept coming. According to the CFDA, Lauren is the first and only designer to win four of the CFDA's top honors: the CFDA Lifetime Achievement Award (1991), the CFDA Womenswear Designer of the Year Award (1995), the Menswear Designer of the Year Award (1996), and the CFDA Award for Humanitarian Leadership (1998).

Lauren's vision of America drew heavily from the world of Ivy League preps, but the brand appealed far beyond the country club crowd.

"Insecurity can sometimes make a man do bold things," Cathy Horyn wrote in a profile of Ralph Lauren for the Washington Post. "It can make him create not one world but many worlds. And it can make him think that what he has done is not only good but better. The upshot has been rather intriguing: a quarter-century of glorious ephemera from a designer who can't draw so much as a sleeve. Never could."

In that profile, Lauren couldn't help but describe his legacy in broad, sweeping strokes. "Did I lift America up a little bit? Did I give it a little bit of quality? Because we were known for polyester. People don't remember that. You couldn't buy good things here. America is mass," he told Horyn.

"And so, as I traveled around and got more sophisticated, I started to see what wasn't there, and I became more nationalistic. Every year of my life. And I'd think, 'Why is this country so insecure about what it is?' So, my thing became more than clothes. It became bigger. It became — America."

Lauren's vision of America drew heavily from the world of Ivy League preps, but the brand appealed far beyond the country club crowd.

The Lo Lifes, a Brooklyn gang officially founded in 1988, used to make a show out of shoplifting Ralph Lauren from department stores around New York City back when they first formed; now, it's more about appreciating the Lifshitz to Lauren, self-made billionaire element of the designer's story, as well as showing off vast collections of archival pieces. (Vice interviewed a Lo Life member who at one point had over 1,000 items.) However, the Lo Lifes' influence on Lauren's brand, specifically its place in hip-hop, isn't officially recognized by the company.

"All together, it makes for a potent folk history of capitalist sedition," Jon Caramanica wrote of the group. "In a time when Polo was being made for and marketed to the aspirational white middle class, some of the most rigorously sourced collections were sitting in closets in the Brooklyn housing projects."

That's not to say the company totally eschewed diversity. Ralph Lauren is credited with catapulting Tyson Beckford to supermodel status, making him the first black male model to hold that title. Beckford's Polo ads were lauded when they first appeared, and the Times ran a story on his breakout success. "I believe I'm setting a good example," Beckford told the paper. "The Polo ad says that I'm not a basketball star or a rap star, but an all-American type. It separates me from those stereotypes, which is good."

Models Tyson Beckford and Bridget Hall at a launch event in New York City. Photo: Evan Agostini/Getty Images

"Lauren built a career by brazenly positioning himself as the quintessential interpreter of the American zeitgeist," Robin Givhan later wrote in The Washington Post. "More than any designer, he has used America's mythology — our secular religion — for profit. In doing so, he has displayed a keen understanding of our cultural symbols. He can parse the difference between a pair of blue jeans worn with cowboy boots and those worn with a black leather jacket. He sees the romance in a prairie skirt or a well-worn Native American blanket. He knows what it means in our racially conflicted society to photograph a dark-skinned, athletic black man in his preppiest, old-money brand. And he knows how a bright-eyed blonde feeds our vision of Mayflower blue bloods. And as consumers, we have bought into those symbols and made Lauren an extremely wealthy man."

Ralph Lauren went public in 1997 and continued to thrive throughout the early 2000s, opening new lines seemingly on a whim. "At Ralph Lauren, there wasn't that outside perspective," says a former designer who requested anonymity since he still works in the industry. "We all, including myself, had our heads up our own asses. It was just so great to be there that even if we were doing something that we couldn't validate based off of the competitive landscape it was like, ‘Well, this is Ralph Lauren. We can do what we want.' We set the tone."

By 2012, Ralph Lauren stock was trading at more than $170 per share, having shot up by $100 in five years. There was so much faith in the success of the company. "Everybody was just feeling the effects of the money that was rolling in, and that it was on a steady incline," says the former designer. The company employed approximately 25,000 people in 2012, and was reporting $6.8 billion in sales and net profits of $681 million.

Then came the slide and Ralph Lauren's literal and metaphorical stock began to tumble. Shares fell nearly 50 percent from a high point of $192 in May 2013 to $82 in February 2016. Sales were still holding steady, but profits slid drastically.

"I used to feel really good about working for that company, but there was so much uncertainty for so long and the lack of communication from the top down was almost absurd."

Underlying problems with the company's organizational structure became more pronounced as the good times gave way to struggling years. "People were just so unhappy," says the former designer. "I used to feel really good about working for that company, but there was so much uncertainty for so long and the lack of communication from the top down was almost absurd. You didn't even know what your job was, you didn't know what your role was. You didn't know if you were going to have a brand the next day."

Several former employees pointed to that lack of communication as a real point of frustration within their departments. "It was like nowhere I had ever worked before," says an employee who worked in materials sourcing for the company's volume brands. "Everyone worked in silos. Manufacturers had one job that they were specific to and the designers only had to report to other designers and we really were kind of bumping into each other trying to do our own jobs. It was really inefficient."

Compared to other retail companies where she had worked, the former employee was surprised by how many managers were assigned to each department. "Ralph is a very, very top heavy company," she explains. "It was a lot of management and not a lot of doers, which is a huge problem."

The organizational problems had long bled into the company's dealings with its wholesale accounts. Michael Schumann, the owner of furniture retailer Traditions, eventually cut ties with Ralph Lauren after years of headaches associated with selling Ralph Lauren Home products in his stores.

"It was no longer worth it to put up with the bullshit in order to have the name, which was too bad," says Schumann. He recalled how Ralph Lauren Home would issue beautiful, hardbound catalogs to stores and then not refresh them for two years since it was too costly to produce the books every six months when new collections would come out.

The rules around where and how to advertise the product were extra strenuous; Ralph Lauren's logo had to be twice the size of the retailer's logo, and ads could only be placed in premium locations. Schumann found success selling Lauren Home, a less expensive line, but then Ralph Lauren implemented a rule that Lauren Home and Ralph Lauren Home couldn't be sold in the same store. "It was just impossible to work with these people," Schumann says.

David Lauren with his parents Ricky and Ralph Lauren. Photo: J. Vespa/Getty Images

Ralph Lauren's managerial structure was broken, relationships were being severed, the quarterly financial reports got more and more alarming, and Ralph Lauren himself wasn't the same radical young guy wooing customers to buy into his dream lifestyle. Change was needed.

For years, David Lauren, Ralph's only child who works at the company, was assumed to be the heir apparent. In 2006, The New York Observer wrote that it was "clear" Lauren would run the company at some point. Fast Company mentioned "industry-wide speculation" that he would take the throne in a 2011 profile. In 2014, Business of Fashion noted that many in the industry pegged the son as the father's successor.

But when the time came for Ralph Lauren to relinquish his CEO title, David Lauren's name wasn't called. Instead, it was Stefan Larsson, a young retail industry darling who built his career at H&M and wowed the industry with a successful three-year stint as the brand president of Old Navy, who would inherit the crown.

When Lauren and Larsson tell the story of how they met, it often includes the tale of a magical first dinner together. Both walked in wondering what the hell they were doing there, both came out knowing that this partnership needed to happen. Larsson is a young star just as Lauren was back in the day, and Larsson has entrepreneurial roots as well — he started his own company to put himself through business school, according to the Financial Times.

Larsson also passed the most crucial test, in Lauren's eyes. "He understands what dreams are," Lauren told the Associated Press when Larsson's new role was announced. (Ralph Lauren declined to make Lauren, Larsson, or any other executives available for comment for this story.)

"In terms of where Stefan is, I saw that he had the background and the excitement and the energy and the knowledge that I don't have."

David Lauren still retains his position as a company executive and a member of the board of directors, and if the new dynamic is awkward, it only comes through a little bit. At the company's inaugural Investor Day presentation in early June, where Larsson laid out his plan for the future of the company, Lauren took the stage for about 20 minutes to talk about the brand history and endorse Larsson.

"I've had great people in my company over the years, wonderful people," Lauren told analysts in the meeting. "But whether someone's going to carry the CEO flag was a different thing because I'm entrusting my baby to him. And that baby has to grow up. And that baby is in the front row, David on the one hand and uh, Stefan on the other. But in terms of where Stefan is, I saw that he had the background and the excitement and the energy and the knowledge that I don't have."

Larsson spent nine months from the point of the initial CEO announcement last September to the Investor Day this summer to take stock of the business and figure out what needed to change.

For those watching the turnaround, there's a lot of optimism about the possibilities under Larsson's leadership. "When you look at Stefan and some of his core competences and what he brings to the table, it's his ability to truly understand and diagnose a weakness within a company and go forth and make the necessary changes," says Jerry Sheldon, an analyst for IHL Consulting Group.

"He really seems to have an understanding of consumers and is able to articulate that understanding, turn it into a business strategy, and execute on that strategy in a very effective way," notes Sheldon.

First up, Larsson is assembling a new executive team filled with people from companies like H&M and Amazon. New blood will likely be just what Ralph Lauren needs. In recent years, employees witnessed how the old guard, which had been in their roles for years and years, weren't cultivating an innovative environment anymore. There was also a sense that Lauren could not be questioned.

"When Ralph has an idea and starts something, nobody ever stands up and says, ‘Hey, this is not right. This is not the way to go,'" notes the former designer. "Everybody just kind of kneels to every word that comes out of his mouth. And when he personally would ask for opinions and direction, people had it and they didn't voice it until he was out of the room, and that was just the way that it went for years and years."

The finale of Ralph Lauren's spring 2011 runway show. Photo: Paul Morigi/Getty Images

"If anything, I see the old management team as being beholden to Ralph and that was probably part of the problem," says Paul Swinand, a retail analyst for Morningstar. "It wasn't that he had lost his touch or that he was too old — you might have thought that — but it also might have been that the old management team was not trying to go out and create anything new, they were just trying to get along and finish out their last few years."

Larsson's public diagnosis of the company's problems was unveiled via the aptly-named Way Forward plan. The main points include a new, more hands-off employee structure (eliminating three levels of management), cutting down the time from initial development of a product to getting it on the sales floor to nine months (down from 15), improving communication between departments, and focusing on three core brands while maintaining a smaller stable of secondary ones. The Way Forward also detailed 1,000 job cuts and 50 retail store closures.

"From a nostalgic, brand-loving perspective, I feel sad about the layoffs, and I'm very fearful that this will be like the JCPenney situation from a few years back," says a former employee in Ralph Lauren's digital operations, who requested anonymity. "But from the business side, it makes a lot of sense to me. Our department did not need three managers."

Larsson is also pulling back from outlet stores, a market where Ralph Lauren had previously been expanding, and cutting down on promotional activity to try and retrain customers not to associate discounts with the brand.

"If anything, I see the old management team as being beholden to Ralph and that was probably part of the problem."

In addition, Ralph Lauren has a huge wholesale business which accounts for nearly half of the company's overall revenue. Macy's in particular is a significant Ralph Lauren buyer; that account alone accounts for about 25 percent of the company's wholesale revenue. But Macy's reported a terrible financial quarter in May, and it doesn't look like it will be making a comeback anytime soon.

"The department store channel is losing market share in general," says John Kernan, an analyst with Cowen & Company, "and Ralph Lauren, the brand, needs to find new channels of distribution like Amazon and other areas where they can grow."

Ralph Lauren is going through operational struggles during not only a tumultuous period in the retail industry, but also a time that's seeing a cultural shift away from what the brand stands for. The prep aesthetic has always smacked of privilege, something accessible primarily to white people with trust funds and monogrammed shirtsleeves. Now, the WASP lifestyle that completely captivated Lauren as a young entrepreneur is considered out of touch at best, offensive and oppressive at worst.

Take, for instance, the media's reaction to the company's Olympic uniform designs this year. Headlines announcing the kits included: "Ralph Lauren's Olympic Uniforms Are Straight Out of Prep School Hell"; "USA's Olympic Uniforms Are WASPy Bullshit"; "Team USA's Official Olympic Uniforms are Peak Vanilla"; and Racked's own contribution, "I Need More From Team USA's Olympic Uniforms". The Daily Mail rounded up the best tweets from the debacle. The comments on Ralph Lauren's own Instagram post of the outfits were littered with prep jokes of varying degrees of wit.

"The uniforms couldn't play more into the world's most unflattering stereotypes of Americans unless they added cigars dangling out of the athletes' mouths, Bibles tucked under their arms, and $100 bills falling out of their pockets," Christina Cauterucci wrote for Slate.

Christian Chensvold, founder of the website Ivy Style and a regular contributor to Ralph Lauren's RL Magazine, broached the subject in a series of posts last fall that questioned whether the Ivy League look was still politically correct. This included a satirical post that imagined a social justice warrior responding to different aspects of Ivy style (example: "Dinner jacket: Offensive to the underfed"); some readers were not amused.

The spring 2016 Polo Ralph Lauren presentation during New York Fashion Week. Photo: Fernanda Calfat/Getty Images

"I would imagine that some of your readers would certainly find ‘club ties' exclusive and elitist," one commenter wrote, referring to a line joking that club ties should be banned for their exclusionary symbolism. Club ties, identified by their repeating motifs, actually did historically denote membership to elite clubs. "I know clothing itself is not elitist; it is the choice behind what we wear that speaks volumes about who were [sic] are."

Later on, when Chensvold published an April Fools' post detailing how preppy style had been banned from college campuses due to the classism and racism that it signified, plenty of readers thought it was real news.

Today's shoppers are interested in more democratic clothing options — options that are casual, practical, and mass. Athleisure is a $97 billion business in the US, accounting for nearly one-third of the entire apparel, footwear, and accessories market. Vetements, the French design collective led by Demna Gvasalia that no one can stop talking about, is making a killing off of what can best be described as incredibly ordinary clothing. Its spring 2017 show, held during haute couture week in Paris, featured collaborations with 18 different brands including Juicy Couture and Carhartt.

"Sometimes, I hear designers from older generations saying, ‘Oh, fashion needs to make women dream,'" Gvasalia told W in an interview earlier this year. "I feel that this is really difficult today. I think it's dated. Fashion shouldn't make you dream in 2016. It should just be there, for us to wear." It's not hard to imagine Lauren burying his head in his hands over that one.

"It could become a social liability to look really old money and traditional, to wear this kind of stuff."

"Ten years from now, when fashion is coming back around in its cycle and these young people are now well into their careers — assuming they have careers with the economy and their crippling student loan debt — when they become 35 years old, are they going to be wearing navy blazers and Alden tasseled loafers and striped ties because that epitomizes success and so forth? I don't know," says Chensvold.

"Theoretically, it could be a version of what we had in the late 1960s with the counterculture revolution," he continues. "This is an election year; the country is more polarized than ever. It could become a social liability to look really old money and traditional, to wear this kind of stuff."

Rebecca Tuite, the author of Seven Sisters Style, a book chronicling the history of the women's equivalent to Ivy League style before many of the actual Ivies were co-ed, sees what's happening now as a less vitriolic version of the backlash to ‘80s prep.

The counterculture revolution of the late ‘60s and ‘70s ushered in an era of long hair and bell bottoms as a response to the conservative style of the ‘50s. Then, in the ‘80s, Lauren led a massive preppy revival that other traditional menswear retailers like Brooks Brothers and J.Press also felt the effects of. This aligned with the Reagan era, a time when conservative politics replaced the freewheeling ideals of the previous two decades. When Lisa Birnbaum published The Preppy Handbook in 1980, it was meant to satirize the prep scene that was reemerging, but ended up being regarded as a literal handbook. The Financial Times described Ralph Lauren as the greatest fashion beneficiary of the book, saying he "cashed in as the preppy wannabe's clothier."

Then the pendulum swung back away from prepsters in the ‘90s, when grunge became the go-to cool kid look. But in the early aughts, prep was popular yet again. Birnbaum published a sequel to the Handbook called True Prep. Lauren's business was on an upswing. Abercrombie & Fitch had infiltrated every high school in America.

"For some, the Lauren prep has become cliché, but actually I think that there is so much genius involved in his reinvention of preppy traditions and that is why whenever the preppy trend circles back to the top, it's Ralph Lauren who is right there, front and center, leading the pack," Tuite explains in an email. "He offers a closet full of preppy staples that perennially sell well, but can still bring a fresh take on a well-trod fashion path."

Men's looks at the most recent Polo Ralph Lauren presentation. Photo: Randy Brooke/Getty Images

And now, here we are again, back at a place where anti-establishment sentiment runs deep. How does a company like Ralph Lauren react to these cultural ebbs and flows? By giving its take on whatever the look of the moment is. In a roundup of old Ralph Lauren advertisements, Vanity Fair captioned a ‘90s ad featuring a cropped long sleeve top and a denim maxi skirt as: "Ralph Lauren did grunge?!"

Patricia Mears, the deputy director of the museum at the Fashion Institute of Technology, remembers observing how Lauren's merchandise morphed to speak to different generations when she was conducting research for a book and exhibition on Ivy style at FIT in 2012.

"When we were looking at images for the book, one of the things that we saw was a more recent photo shoot with young men, handsome, Ralph Lauren-esque. They were wearing certain things like beautiful crested navy blue blazers, but then they also had knitted caps like what you'd see on surfers or skaters," says Mears. "Ralph was very smart about incorporating things like skate culture into a look that is still going to include the cornerstones of the Ralph Lauren vocabulary. It will still have chino pants or a navy blazer, but the T-shirt and the hat and some of the other accessories are going to be much more cutting-edge and something that a twentysomething today can relate to."

Recently, some of Ralph Lauren's lines have a boho feel in accordance with current trends. Carly Heitlinger, the blogger behind The College Prepster, says she doesn't consider Ralph Lauren a traditional prep brand based on the current women's merchandise, because it is so fashion-forward.

"A lot of their designs are a little bit trendier, a lot of crochet and knit," says Heitlinger. "I'm sure you could find a piece or two within each collection that fit into more classic, traditional outfits like the button-downs, but there's a lot of trendier stuff in there too. I think they really embraced this bohemian look." She isn't buying much from the brand these days, but says she would shop it more if it moved back towards its traditional prep roots.

No matter how the brand may change under its new CEO, Lauren's own effect on fashion will always be far-reaching. So many designers have come up under his tutelage, from Vera Wang to Thom Browne to Tory Burch. His reputation in the industry precedes him.

"I asked Marc Jacobs one day, ‘Who's your favorite designer?,'" says Mears. "At first when he said Ralph Lauren, I thought that was an interesting choice, but then he elaborated that there's no person in the world who has done a better job of galvanizing that classical American look and turning it into an empire. When you see a Ralph Lauren piece you really know you're looking at Ralph Lauren. He said that he's probably the best designer in the world at that."

And as the company looks forward, Lauren is adamant that Ralph Lauren will continue to be "a part of life," as he told analysts at that Investor Day meeting. "This is about creativity, about life," he said. "It's not did we make a new shirt, look at us, we made a shirt with three buttons. It's about living. It's about dreams. And everyone has a dream."

Erika Adams is a Racked contributor.

Editor: Julia Rubin



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