The Daring 25: Clothing Trendsetters

Produced with  GQ Style

Cadillac is passionate about innovations that drive us forward, so we partnered with five Conde Nast publications to discover individuals who use their talents to do the same. We asked the editors of Vanity Fair, Wired, Architectural Digest, Bon Appétit and GQ who they found most daring in 2016.

The Daring 25 are innovators, creators and pioneers who are trailblazing in their fields. These impressive individuals and companies stand out in the industries of entertainment, technology, design, food, and style, and represent the best of those who challenge the status quo.

These five designers and retailers are bringing boutique menswear to the masses.



Just a few years ago anyone who listed more than one profession on his passport was regarded with suspicion as a dilettante or dabbler. But in today’s interconnected, entrepreneurial, constantly changing environment, the best way to achieve success and maintain relevancy is to diversify your personal portfolio. Right in the vanguard of this new generation of enterprising multitaskers is fashion designer, DJ, and creative director Virgil Abloh.

Abloh has worked as Kanye West’s creative director for 13 years, helping oversee his videos, concerts, merchandise, and DONDA, West’s creative agency. At the same time, Abloh has pursued a DJ career; opened a retail store in Chicago, RSVP Gallery; and launched two clothing brands. The 36-year-old is now making his mark in the fashion world with his label Off-White, which mixes his distinctive custom logos, skateboard culture, and a streetwear edge with a high-end aesthetic. The collection, whose fans include Beyoncé, Rihanna, and Takashi Murakami, earned a 2015 nomination for the prestigious LVMH Award. Abloh was the only American designer that year to be nominated.

Abloh grew up in Chicago in the ’90s, during Michael Jordan’s sports reign, and earned a degree in civil engineering at the University of Wisconsin–Madison, followed by a master’s in architecture at Illinois Institute of Technology (IIT). He references his technical training in his creative pursuits. “The world is made up by the merger of those two things,” he says. “Buildings don’t get built without a vision of what creatively they’ll look like … My background gave me the foundation of making a career in creative endeavors that utilize both.”

“Off-White stands for a case study in nudging the definition of fashion forward.”
Virgil Abloh

In 2002, two years before West’s breakthrough album, The College Dropout, was released, Abloh quit a job at an architecture firm to become West’s creative director. The longtime collaboration, Abloh says, is the best job he ever had. “Kanye is the greatest artist, designer, and musician living and is dedicating his life to the modernization of culture,” he says. “The goal is to work together for 45 years.” West has returned the compliment, declaring Abloh, “one of the smartest, fastest, most innovative people I’ve created with.”

Simultaneously, Abloh channeled his love of skateboarding, ’90s hip-hop, and other musical genres into his own fashion pursuits. He first gathered discontinued Ralph Lauren Rugby flannels and printed oversized logos over them for a collection called Pyrex Vision, which Abloh says was “less a clothing line than it was a music video that had clothes.” Abloh shuttered Pyrex after one year, but channeled his energy into a more fully formed collection, Off-White. Its mixture of street style and luxury men’s and womenswear—there are still logos and graphics, but there are also luxe leather trench coats and tailored dresses and jackets—has caught the attention of industry insiders by redefining what luxury clothes mean to a younger generation, which often takes its fashion cues from Instagram and YouTube.

“Off-White stands for a case study in nudging the definition of fashion forward,” Abloh explains. “This generation has the Internet, and is way more global. With social media, knowledge is shared instantly, and when something happens in the world, it can be more impactful there than when it’s a headline on a newspaper.”


Abloh has caught the attention of industry insiders redefining what luxury clothes mean to a younger generation.

The LVMH nomination last year, says Abloh, was “a tremendous milestone to help understand where I wanted to go with Off-White. It was self-validation that the fashion world look at what I was doing as fashion, not just a clothing project.”

Off-White has evolved into a lifestyle, with Abloh starting to open retail stores across the globe; publishing a book, You Cut Me Off, based on the backstage action before and after his Fall 2016 menswear show; and recently announcing a collaboration with Moncler.

Abloh’s in no mood to slow down. “You’d be surprised how much you get done if you just constantly work,” he says. “I look at it as I’ve been given a tremendous opportunity. Most people think in 9-to-5 terms or in ‘I need a vacation’ terms. For me, it’s not a chore. For me, I don’t work any jobs. I’m just into the things I’m passionate about, and I do them.”



The first location of The Armoury was doomed to fail—that is, according to its feng shui. “It was in an old building on the third floor at the end of a hallway that was not occupied for 10 years,” explains the clothing store’s founder, Mark Cho. “In Chinese feng shui, if you’re at the end of the corridor, it’s unlucky; it means your business will end. But I liked it—I just felt something particular to that space.”

Good thing Cho wasn’t afraid to break a taboo. Despite its supposedly ill-fated location, Cho’s atelier for bespoke suits and expertly crafted shoes and accessories quickly became a destination for a new generation of well-dressed men from Hong Kong and beyond. The Armoury has since expanded to include an additional outpost in Hong Kong as well as one in New York. And in 2010 Cho acquired Drake’s, a traditional British manufacturer of ties, shirts, and scarves, gaining a foothold in the heartland of heritage menswear.

“For me, daring is to go against the grain, against trends, occasionally logic and the most rational choice, and to stand alone,” says Cho After a brief stint working in womenswear for Jill Stuart, Cho pursued a career in real estate, first in London and later Malaysia, where his penchant for tailored office wear made him stand out from his coworkers. “People would ask me if I was going to a wedding, because I would wear a jacket and tie,” says Cho. “They were these dumpy-looking guys in polo shirts. It really frustrated me.”

“Daring is to go against the grain, against trends, occasionally logic and the most rational choice, and to stand alone.”
Mark Cho

Looking for a change of pace after his father’s death, he ditched his lucrative real estate career to launch The Armoury with business partners Alan See and Ethan Newton. Cho had a close connection with a tailor in Hong Kong, W.W. Chan. “After a while, I was helping him do trunk shows in London. I’d organize hotels and clientele and help him as a sales person,” Cho says. When The Armoury opened, the tailor let the upstart take orders for him on his behalf. “That provided the initial clientele, and that made me more comfortable taking this weird floor at the end of the corridor of the building to start a business,” Cho says.

The Armoury stocks shoes by Saint Crispin’s and shirts by Ascot Chang among its international roster of tailors and craftsman, often introducing smaller independent designers to a global clientele they may not usually reach. “Region to region, the look is different,” Cho explains. “The Florentine cut is different than the Milanese cut or the English cut. We have a Japanese tailor who specializes in American tailoring from the ’50s and ’60s.”

Cho finds most of the The Armoury’s goods by word of mouth. “New tailors don’t pop up that often,” says Cho. “Tailors talk and they’ll recommend. They’re like artists in that way; they talk about each other and each other’s work. They also want to know if they’re doing the same work as someone else, because they always want to stand out from the crowd.”

While growth is still on the horizon—Cho wants to expand his in-house line of shirts and accessories—one of the entrepreneur’s boldest ploys is resisting the pressure to over expand. He says the future doesn’t hold many more Armoury stores, given the handcrafted work of its vendors. “The Armoury stocks designers who make 60 bags a year. You can’t have too many shops.”



For Jill Wenger, fashion is not about the latest trends. “I’m influenced and inspired by designers and artists who create what they believe is good in spite of what’s in style,” she says.

To that end, her minimalist-driven boutique Totokaelo stocks timeless pieces by designers like Haider Ackermann, Issey Miyake, and Dries Van Noten. The seasonless mix has proven a hit with shoppers. Between two stores and its online business, Totokaelo earned an estimated $17 million in sales last year. At a time when the fashion industry is struggling with consumer fatigue brought on by trend overload, Wenger’s more considered approach could serve as a model for her peers in retail.

Wenger grew up in Texas and always had an entrepreneurial spirit. As a kid, she says, “I was always re-strategizing the placement and pricing of my lemonade stand. My favorite toys were an adding machine and a day planner.”

After studying entrepreneurship in college, she traveled to Australia and Ireland. She then landed in Seattle, following a brother who had moved there for a job at Boeing. She worked as a window display stylist for Anthropologie, putting a second degree in graphic design to use.

“Shoppers come to Totokaelo when they don’t want to look like everyone else. Blending.”
Jill Wenger

Nine months later, she took the plunge and opened her first retail store in a 400-square-foot basement studio. She named her consignment shop Impulse. “My intention was to put beautiful things in a space and help people figure out what they wanted to say to the world and help them say that.”

After finding success stocking local vintage brands, she opened Totokaelo (which in Latin roughly translates to “the sky’s the limit”) to sell forward-thinking designer labels. That included a proprietary line of women’s clothes.

It grew into a destination for people who are “intelligent, creative, confident, and originals,” Wenger says. “Shoppers come to Totokaelo when they don’t want to look like everyone else. Blending in is boring. Having an ‘it’ bag doesn’t mean anything anymore.” In 2015, Wenger took a gamble on a second outpost of Totokaelo in New York. The learning curve was steep. “Our contractor walked out two weeks before the store opened,” she said. Her employees worked overtime to paint walls and hang shelves. On opening day, there were holes in the walls where speakers were supposed to be installed. “Everything that could have gone wrong, did,” she says. “I learned a ton. I now know 239,482 things not to do when opening a retail store in New York City.”

But none of that has deterred Wenger. To her, daring is “doing whatever it takes to accomplish something you believe is important.” She adds: “I believe that when something is 70 percent awesome, we should just do it.”



There are legendary tales of young entrepreneurs dropping out of college to found massively successful tech empires. Arun Gupta’s isn’t one of them. Gupta decided to leave Yale University in his junior year in 2009 to run a start-up called WakeMate, a wearable alarm clock that gave users readings on their sleep patterns. The company sold just 10,000 units in 10 years, then Fitbit hit the market. Then Jawbone. Soon, WakeMate was out of business.

“I ended up going back to school, finished my last three semesters at Yale, and got a degree in physics,” explains Gupta.

But Gupta, now 27, hadn’t lost his zeal for start-ups. He combined his science background with his real passion—fashion—and created a website to sell coveted luxury men’s clothes and accessories: Grailed.

Grailed is the ultimate online marketplace for hard-to-find, high-end fashion items for men. Searching for those Yeezy Boosts from last season? Grailed’s got ’em. What about those Rick Owens drop-crotch black wash jeans you’ve been coveting? Yup, Grailed has them, too.

Just a few years ago, you’d have said Gupta was crazy to think there was a big enough audience for a venture like this, but he’s poised to capitalize on the recent explosion of interest in high-quality, adventurous fashion among young men. (It’s no coincidence that menswear bro and former Four Pins editor Lawrence Schlossman works for the site.) Grailed already attracts 90,000 monthly users shopping the coolest goods vetted and sold by their peers. This time it looks like Gupta’s risk-taking is going to pay off.

“More men are spending dollars on fashion. Department stores are putting more time into their men’s selections. It’s okay for guys to care more about fashion.”
Arun Gupta

Gupta was into clothes even as a teenager. “I wore J.Crew and Diesel back in high school,” he says. “As I got older, I was more into A.P.C. and Lanvin.” By the time Gupta was at Yale, sites like Mr Porter and Gilt Man were in their infancy, but he sought out like-minded shoppers on chat rooms and message boards. It was here that men talked openly about their clothing obsessions and bought and sold their one-of-a-kind finds. “I bought some A.P.C. denim at great prices,” says Gupta. “And this was right after college, so I had no money.”

Once he saw the active audience, he wanted to create a marketplace to serve these members. So he coded Grailed, using the chat rooms as focus groups.

“It was by the people for the people,” Gupta says. “I announced its launch on Reddit. For the first six months, it was me in my bedroom working on this and talking to the people on the forum. They would give feedback and say, ‘I wish I had a wish list or a shopping cart,’ and I would spend time making those features.”

Today, the New York–based Grailed lists nearly 50,000 items on its site a month. The site attracts sneakerheads and celebrities, suburban dads and Brooklyn hipsters who love Raf Simons, Vetements, Hood By Air, and Acne Studios. The company doesn’t carry inventory, instead hosting a network of over 20,000 users who buy and sell their own luxury goods, setting prices significantly lower than what’s at retail. The goods are both new and used, but if used, they’re still in pristine condition.

“One of the great parts about Grailed is that you’re experimenting with used stuff,” says Gupta. “Maybe it would be a frivolous purchase if you bought it new.” On Grailed, he says, “You don’t have to spend a ton of money,” and if you’re not happy with a purchase, “You can just resell what you just bought.”

Gupta has noted how men’s shopping has evolved since the time he was browsing chat rooms. “Before, it wasn’t considered manly,” he says. “Now rappers and celebs are noticeably into fashion. More men are spending dollars on fashion. Department stores are putting more time into their men’s selections. It’s okay for guys to care more about fashion.”

And for Gupta, that’s one wake-up call he’s happy to hear.



When you think of fashionable cities, New York, Paris, and London usually come to mind first. Aaron Levine is currently making a case for an alternative: Columbus, Ohio.

Last April, Levine left the Big Apple to oversee menswear at the Columbus-based Abercrombie & Fitch. The designer has his work cut out for him—Abercrombie has suffered from slumping sales and a tarnished brand perception under former CEO Mike Jeffries, who abruptly left in 2014. Levine, who previously applied his vintage-cool-meets-modern-swag aesthetic to a well-received men’s collection at Club Monaco, welcomed the challenge. “I like figuring out solutions and building things,” he says. “What fun would it be to go someplace and they’re like, ‘Okay, we’re [already] perfect’?”

His goal: to transform the 124-year-old Abercrombie, a retailer most recently known for shirtless models and logo-strewn clothes, into an elegant men’s brand with a more polished ethos.

“I like figuring out solutions and building things...What fun would it be to go someplace and they’re like, ‘Okay, we’re [already] perfect’?”
Aaron Levine

Aside from pulling from Abercrombie’s own fashion archives, Levine plans to reference his love of vintage finds, a passion he developed while growing up in Virginia. “I would buy stuff that I wouldn’t even wear because I liked having it,” says Levine. “I would shop surf shops, and army/navy stores were treasure troves. Or [preppy East Coast men’s retailer] Britches. When you combine all those different things together, vintage military with prep with surf shop stuff, that’s what I thought was really cool.”

The designer attended college at Virginia Tech, but Levine dropped out of school after a few years. He crashed on friends’ couches in Richmond, Virginia, until he found a gig as, ironically, an assistant manager at the local Abercrombie. This was back when the store employed shirtless models to greet guests at the door. “I wore a shirt,” Levine notes.

While there, he discovered fashion as a career calling. “I would look at a shirt and decide whether or not I would buy it, and if not, what would I do to make it cooler?” he says. “Then I thought, ‘I could do this.’ I went back to school and changed my major and went into fashion merchandising.”


Levine's goal is to transform the aged retailer A&F into an elegant men's brand with a polished ethos.

After stints at labels including Hickey Freeman and Jack Spade, Levine joined Club Monaco. He made its previously rather bland menswear so hot that it started selling on men’s e-commerce site Mr Porter alongside Public School, Givenchy, Acne Studios, and Burberry. Three years later, he got a call from Abercrombie, which wanted him to work the same creative magic on its brand.

Levine has already toned down the tacky logos, played up the more classic, military-inspired elements of Abercrombie’s past, and improved the tailoring. “There’s that heritage there already,” he says. “So we just played with that, and tried to kick the can down the road and make it applicable for now, paying attention to fit, fabric and really caring about the product.”

Still, he recognizes change for Abercrombie will take time. In the meantime, he’s enjoying his more relaxing Ohio commute. “I lived in New York for 15 years, and I commuted almost four hours a day, between driving to the train and getting to Grand Central. Now I drive back roads through farm lands for 25 minutes a day. It’s a perk for sure.”

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