LOS ANGELES, United States — It's an early Monday evening in Hollywood. The mid-October sun has already set and the air is cool, if not chilly. The cast of Amazon Prime's newest docuseries, The Fashion Fund, chat with fellow guests at a relaxed cocktail party on the rooftop of upscale shared workspace NeueHouse, which recently opened its first Los Angeles outpost in the historic CBS Radio building.

The cast isn't composed of actors or even reality stars in the traditional sense. Nor would they particularly like to be considered a cast. Instead, they are fashion designers in the running for the Council of Fashion Designers of America/Vogue Fashion Fund prize. The annual competition, established in 2003, has ignited the careers of nearly every significant American designer under the age of 40. Past winners include Jack McCollough and Lazaro Hernandez of Proenza Schouler (2004), Alexander Wang (2008) and Joseph Altuzarra (2011). This year's winner, who will be announced on November 2 at a dinner in New York City, will receive $400,000 in cash, as well as a year's worth of mentorship from an industry leader. The two runners-up will receive $150,000 each, as well as mentorship.

It’s nearing the end of the evening’s festivities and this year’s 10 finalists, two of whom are duos, are flirting with Los Angeles fashion’s finest as they wait for their microphones to be removed by the team from Break Thru Films, the production company behind the show. Cadet founders Brad Schmidt and Raul Arevalo have formed a circle with Vogue contributing editor Lawren Howell, and Jonathan Simkhai is posing for a photo with Eva Chen, Instagram’s head of fashion partnerships.

Chrissy Teigen and John Legend, the night's marquee guests, are long gone. In the corner, a Break Thru field producer gives headset-wearing co-workers a pep talk. Tomorrow is a big day, he says. It's true. Tuesday will be the culmination of three months of work carried out by the competitors, judges and film crew alike, starting with a fashion show at the Chateau Marmont, followed by afternoon tea and, later on, an 80-person dinner at Bouchon in Beverly Hills, hosted by Kanye West and his very pregnant wife, Kim Kardashian West. "Kim is my dream Chromat girl," remarks designer Becca McCharen, who uses her architecture degree to construct cage-inspired lingerie, swimwear, activewear and more.

Anna Wintour, Kanye West and wife Kim at the CVFF fashion show | Photo: Jeff Vespa/Getty

As the crowd thins out, a pile of Fund-ers, including CG’s Chris Gelinas and Baja East’s Scott Studenberg and John Targon, file into the elevator. Most of them arrived from New York on Saturday and have spent the last two days producing videos for Instagram, the latest in several challenges brought forth by the judges over the course of the competition. While they weren’t required to design any new clothes for the fashion show, they’re eager to blow off some steam before the mid-day schmoozing begins. So it’s off to West Hollywood’s famed Saddle Ranch, where there are promises of mechanical bull riding. Too bad the cameras aren’t there to witness that.

If it all sounds a bit surreal, that's because the CFDA/Vogue Fashion Fund (or CVFF for short) is what industry dreams are made of. For those familiar with the Greek system — the North American tradition of organising university social groups into what are called sororities and fraternities — the annual trip to Los Angeles, which has been a part of the programming for the past 11 competitions, could be compared to the end of the so-called pledge (or initiation) process. Rubbing shoulders with celebrities, staying at the Sunset Tower, meeting Kim and Kanye, being recognised by American Vogue editor-in-chief (and Condé Nast artistic director) Anna Wintour: These moments give participants, some of whom haven't even hit $100,000 in annual sales, a feeling of acceptance into a world that is still rarefied.

But more than 10 years after the inaugural prize was awarded, where does the value of the CFDA/Vogue Fashion Fund truly lie?

The CVFF was established in 2003, a year that marked a notable shift in American fashion — namely, the emergence of Proenza Schouler, a label run by two fresh-out-of-Parsons twenty-somethings, whose designs were imaginative and exciting enough to earn international recognition. At that point, McCollough and Hernandez were best known for their structured, inside-out lingerie tops and for the fact that Barneys New York bought their graduate collection straight off the university’s catwalk. But at the time, this kind of swift success was unheard of. New York, back then, was not as welcoming to young fashion designers as it is today and Wintour saw an opportunity to help by staging a competition.

The seed, however, was planted two years before, in 2001, during the dark days after the September 11 terror attacks. "September 11 was the very first day of New York Fashion Week," Wintour recalls. "As a result, every fashion show was cancelled. The big designers were able to regroup and show in a different way, but what became very obvious to us was all the younger designers had put down their deposits, lost them and did not have the financial wherewithal to have another show." With the help of designer Carolina Herrera, who lent out her showroom, Wintour and her team at Vogue organised a runway show for said designers just a few weeks after the attacks. "From that came the realisation that these young designers were living a hand-to-mouth existence, and that they needed mentorship and support," Wintour says.

It took some time for Wintour to organise and raise money for the first competition, which happened in the autumn of 2004. More than 170 designers submitted their names for consideration. Just 52 were asked to move on to the second phase of the competition, and only 10 were selected as finalists. That year’s group included Derek Lam, Behnaz Sarafpour, Peter Som and Libertine. Runners up Habitual and Cloak won $50,000, while the winners — Proenza Schouler — won $200,000. “We were all very much in agreement that we didn’t want to just hand out another award,” she says.

The editor and her judging panel — which at the time included Robert Duffy, Narciso Rodriguez and Julie Gilhart — spent several months visiting the competitors' studios. "We really wanted to get to know our finalists," she continues. "One of the points, right from the beginning, was that these designers had to be in business for two years. We didn't want designers who were just coming out of school. We wanted to be able to look at a body of work and understand their business sense and design ability."

The process may be more regimented today than it was in 2004, but the foundation remains the same. The finalists — who are each featured in the November issue of Vogue, this year alongside model Kendall Jenner — are asked to complete a series of challenges, which take place between mid-July and November. This year, Fossil sponsored a design challenge, Kate Spade sponsored a marketing challenge and Instagram sponsored a social-media challenge. They must complete these tasks, spend half-a-week in Los Angeles and welcome every judge — as well as a camera crew — into their workspaces on a continual basis, all the while maintaining their regular production schedule. More than anything, it’s an investment of time.

But the payoff can be great. Along with the money, each winner is also granted a year-long mentorship with an industry leader, which remains a core tenet of the programme. (The CFDA also provides on-going mentorship to all finalists through its Business Advisory Committee, which includes 3.1 Phillip Lim chief executive Wen Zhou, Alexander Wang president Rodrigo Bazan and Coach chief executive Victor Luis, amongst others.) Indeed, out of the nearly 30 past and present participants who spoke to BoF about their time spent in the competition, every single one named mentorship — both formal and informal — as the most meaningful part of the process.

Prabal Gurung, who was a runner-up in 2010, maintains a steady relationship with his mentors Carolina Herrera and her former chief executive Caroline Brown, who now leads DKNY. "From accounting to financials, I guarantee I would not be here without their help," says Gurung, who used his award money to produce his first Resort collection. "It completely changed my business."

Eva Fehren jewellery designer Eva Zuckerman, a runner-up in 2014's competition, says her mentor John Idol — the chief executive of Michael Kors — gives her assignments as a part of their process. "I meet with him on a very regular basis," she says. "He's a really busy person, and for me to get time with someone like that, I don't take that for granted." Fehren, who has struggled with copyright infringement — most notably relating to her signature "X" ring — says she continues to reach out to judges as well. "I feel like I'm still in the Fund," she remarks. "I recently had a business decision and I wasn't 100 percent certain what to do. I called one of the judges and talked through it with him. That, to me, has been so critical. I do feel like a part of the family now."

The judging panel, a mix of industry executives and designers, is an alluring part of that CVFF "family." The current line up includes Wintour, CFDA president and chief executive Steven Kolb, CFDA chairman Diane von Fürstenberg, J.Crew's Jenna Lyons, Theory chief executive Andrew Rosen — who has personally invested in several of the brands that have gone through the competition — designer Reed Krakoff, Neiman Marcus' Ken Downing, Nordstrom's Jeffrey Kalinsky, Vogue fashion news director Mark Holgate and Rag & Bone designers Marcus Wainwright and David Neville.

Wainwright and Neville are unique in that they have participated in the Fund themselves, but have also gone on to both judge and mentor. They didn’t place when they entered the competition in 2006, yet they now run one of the largest businesses to come out of their class, which included Thakoon, Rodarte, Marchesa and 3.1 Phillip Lim, as well as Costello Tagliapietra, Devi Kroell, Subversive, Jovovich-Hawk and Doo.Ri. “We were one of the smaller ones,” Wainwright recalls. The winner, Doo.Ri Chung, left her own label in 2012, although runners-up Rodarte and Thakoon are still in business. The rest of the class has seen mixed results: 3.1 Phillip Lim is now a major player in contemporary-priced fashion, while Jovovich-Hawk had shuttered by 2008. Shoe designer Devi Kroell departed from her namesake label in 2010. Marchesa has cemented its place on the red carpet, while Subversive jewellery designer Justin Giunta, who is also a fine artist, has built a custom-order business.

Much like any startup accelerator, not every designer who has participated in the CVFF has succeeded. In fact, several of the Fund’s finalists are no longer in business or have parted with the brands they founded, including Band of Outsiders, Doo.Ri, Vena Cava, Christian Cota, Moss Lipow and Jovovich-Hawk.

“It’s like a relationship. It’s not just what you get, but what you put into it,” reasons Kolb, who joined the CFDA in 2006. “You can’t sit back and wait for us to come knocking on your door and offer you work opportunities and exposure and advice. You have to ask the questions. Many of the designers who have succeeded have done that well and developed relationships beyond the program.”

To be sure, winning the top prize does not guarantee success. But as the years go on, the criteria for what makes a winner does not seem to be set in stone. While the end goal is always to take the company to the next level, it’s not always clear what that level should be. Is it fair — or does it make sense — to pit Billy Reid against Joseph Altuzarra, or the shoe designer Paul Andrew against luxury knitwear label Orley?

Yet looking back, it’s clear that each CVFF class reflects the state of American fashion at the time. Wang, who won in 2008 before the recession hit, signalled the arrival of the contemporary designer. Billy Reid, 2010’s winner, represented the rise in the importance of menswear to the overall apparel market. Paul Andrew, who took last year’s top prize, reflected the growing significance of accessories.

The American fashion industry has changed dramatically since 2004. Today, dozens of new labels are launched each season. The increase in the number of shows on the New York Fashion Week calendar — from around 150 in the early 2000s to more than 300 in the 2010s — is evidence of this. That proliferation is, in part, thanks to competitions like the CVFF, which bring more exposure to the American fashion industry. The fashion business has also diversified. Designing apparel for women is no longer the only avenue, nor is wholesale the only distribution option. As the menswear and accessories markets have grown and e-commerce has flourished, the barrier for entry has lowered. But it also means that competition has increased.

These factors may explain why 2015’s CVFF class is the most eclectic to date. “We call this our indie group,” Wintour says. “In a way, it’s a very even playing field this year because they are all so different.”

That, they are. Along with Chromat, there is luxury-knitwear label Baja East, founded by two friends who worked in sales for years at major companies including Givenchy and Céline. The Kansas City-based Baldwin, designed by owner Matt Baldwin with support from his business-partner and wife, Emily, is grounded in American-made denim. Brother Vellies’ Aurora James designs shoes crafted by artisans all over Africa. Gypsy Sport, perhaps the wildest of the wild cards, is designed by Rio Uribe, who spent six years in merchandising at Balenciaga before launching his own street-inspired collection in 2012.

Cadet models at the CVFF fashion show | Photo: Donato Sardella/Getty

Many of the finalists produce both women’s and men’s clothing, although three started the competition in menswear only. David Hart focuses on classical styling. Thaddeus O'Neil’s inspiration comes from years spent surfing. Raul Arevalo and Brad Schmidt, the married partners behind Cadet, launched more than two years ago not through e-commerce or wholesale, but by opening a physical store in Williamsburg, Brooklyn. Both Thaddeus O'Neil and Cadet showed women’s collections during New York Fashion Week in September, at the urging of Wintour and the other judges. “We did suggest to them that they should take advantage of the immediate recognition that they received through being one of the finalists and that it’s a wonderful way to take advantage of that,” Wintour says. “If they had the wherewithal to do it, we did recommend it and in many instances the CFDA would try and help them find a space.”

The only traditional womenswear designers are Chris Gelinas, whose intellectual-sportswear collection is priced at the designer level, and Simkhai, who has made a name for himself on the contemporary segment with sexy, form-fitting dresses that err on the side of cool. A decade ago, these two would have been the norm. Today, they are nearly the anomaly.

Indeed, the group — whose annual sales figures vary wildly, with some making just under $100,000 in revenue a year and others bringing in several million — symbolises many of the biggest movements happening in global fashion: sustainability (Brother Vellies), genderless styles (Baja East, Gypsy Sport) and direct-to-consumer business models (Cadet).

However, this year’s grab bag of finalists has spurred observations, if not straight-on criticisms, about how the CVFF operates. Some of the individuals with whom BoF spoke, including those directly involved with the programme, suggested that the number of finalists be reduced to eight, or that the competition, which currently has an endowment of $30 million, take place every other year instead of annually, for lack of a large enough talent pool of contenders, especially in the women’s design category. Yet it’s unlikely that there will be any drastic changes made to the current formatting. “The reality is, there are a lot of brands out there,” Kolb argues. “Every year, I wonder if we are going to get 10 that are worthy, and we always do. I look at the brands that have [participated] and many of them are doing amazing things. If it wasn’t for the program, people in the industry wouldn’t know who they were. I don’t worry that we’re over mining a field. There’s enough talent, enough capacity.”

While there are very few young designers who have not applied for the Fund at least once in their early careers — Hart applied three times before being accepted on his fourth attempt — some eligible candidates have decided not to apply, given the amount of time and effort the process requires, which comes on top of running their businesses. Many of this year’s finalists are one or two-person operations. Of course, O’Neil, who has one full-time employee, launched a women’s collection during the competition at the urging of the judges. “I was totally expecting them to suggest that, but definitely not expecting to do it during the course of the Fund,” says the designer. “But I’m glad I got the nudge.”

Others who have chosen to forgo the experience expressed concern to BoF about being a part of the docuseries, which requires the finalists to be filmed on and off for four months. This season of The Fashion Fund will stream on Amazon during the spring of 2016. “Who would say that?” questions von Fürstenberg. “Yeah, but it gives visibility. I think that’s unfair. This is the world we live in. I mean, come on.”

Along with the exposure, Amazon will also be a driver of sales. Pieces from the finalists' spring collections are slated to be sold on the e-commerce behemoth's website. "This collaboration is part of our on going effort to lend support to the industry where we think we can add meaningful value," says Cathy Beaudoin, president of Amazon Fashion. "In this case, it's just not easy for emerging designers to reach a wide audience early on. So, we wanted to help solve that problem. But we also wanted to give our devoted fashion customers access to these designers and do it all in one place."

The two projects are meant to fuel each other. While the details are still being ironed out, “The idea is to give our customers more context in the form of content as they shop and learn and discover these designers,” Beaudoin says. “Our intent is to have parts of the docuseries in this [shopping] experience so that customers will be learning about the makers and designers behind the product while they shop.”

Initiatives like Amazon's illustrate the breadth of opportunity participating in the Fund can bring. And, while the overall premise of the competition has stayed the same over the years, the prize money has increased significantly. In the past, the winners have created capsule collections for a mass retailer. Previously, it was Gap, then J.Crew. (This year, Uniqlo is the Fund's retail partner and three winners will design a capsule collection to be sold in stores during the summer of 2016.)

The CVFF has also served as a template for other programmes. The British Fashion Council/Vogue Fashion Fund, founded in 2008, follows a nearly identical model. There is also the LVMH Prize, the H&M Design Award and Design Entrepreneurs NYC Award, as well as several that have come and gone since the establishment of the CVFF in 2003. There were fashion prizes long before the inception of the Fund as well. The first recipient of the ANDAM Prize was Martin Margiela, back in 1988, while the International Woolmark Prize was launched in 1953. (Yves Saint Laurent and Karl Lagerfeld won in 1954.) However, the Woolmark initiative went dormant for many years, only to be revived in 2012. Stuart McCullough, chief executive of the Woolmark Company, insists that the re-launch of the programme was not inspired by the prominence of the CVFF, but he acknowledges the need — and demand — for these types of competitions. "I don't think the cheque hurts, but it's really about the media attention that this garners," he says. "We certainly have no shortage of applicants."

Save for the BFC/Vogue Fashion Fund, in the UK, many of these other competitions also tend to operate quite differently than the CVFF. “The LVMH Prize is more of a whirlwind,” says Baja East’s Studenberg, who participated in the French conglomerate’s Spring 2015 competition. “Press, designer and buyers all in one, within three days. With the CFDA you’re sitting down looking at your business — where you are, where you came from, where you’re going. Yes, we met Karl Lagerfeld [at LVMH], but when Anna and Diane came to our place, you’re actually sitting there talking about your business and they’re giving you feedback.”

While these other competitions have certainly attracted interest from the media — or “column inches,” as McCullough puts it — as well as the opportunity to connect with editors, retailers and other industry executives that could make or break a young designer’s career, none of them have the CVFF’s secret weapon. That, of course, is a chance to be noticed by — and potentially form a relationship with — Wintour. “I can email Anna now, and I do,” says one of last year’s runners-up, Ryan Roche, whose knitwear business has more than doubled every season since winning the competition.

“I probably didn’t have much face time with her before the Fund,” says Wang. “I got to know her, express my ideas to her. That relationship has propelled a lot further since I won.” The designer’s namesake brand now brings in more than $100 million in annual revenue (not to mention his stint designing for the house of Balenciaga).

Altuzarra expresses a similar sentiment. “Probably the most important relationship is the one I built with Anna in that process,” he says. “It had the most direct impact on the growth of my business. She has such a 360-degree understanding of the industry. Sometimes it can feel like lip service, but I want to stress how incredibly helpful the Fund actually is. The day after I won, I got calls from Europe. It was a really big deal for me, and it put us on the map in a much more substantial way than we’d ever been.” In 2013, French luxury conglomerate Kering took a minority stake in Altuzarra’s company and his name has been floated for multiple creative director roles at European fashion houses.

Back in Los Angeles, the finalists are shuffling around the famous courtyard of the Chateau Marmont, which Vogue’s West Coast director Lisa Love has transformed into a salon-style runway. "I cast the audience as much as I cast the show," Love says after the annual event. While the seated crowd — which ranged from LA-based designers like Jenni Kayne to celebrities including Solange Knowles and Stephen Dorff — was a delightfully entertaining mix, this year it was the models that proved to be Love’s true challenge. The concept of the show changed at the last minute to reflect the unique positioning of the current class. Love and her team were tasked with finding dancers, drummers, and other non-traditional models to stand alongside the waifs. Each designer's group came out like a little vignette: a day at the beach for surfer Thaddeus O'Neil, a team of steppers for shoe label Brother Vellies. The Wests look on, smiling and nodding their heads to the beat of the drum.

After the show, Rag & Bone’s Neville and Wainwright discuss the finalists’ chances over a plate of charcuterie. “We’ve been talking about Gypsy Sport, Jonathan Simkhai, Brother Vellies quite a lot. Maybe more to the point is who we haven’t been talking about,” Wainright says. “We haven’t been talking about Baldwin at all, haven’t been talking about CG at all. David Hart is a very interesting one. This is someone who, you know, if he had some business under his belt, he’d be a real contender, because everyone loves him. And he’s very good at the creative. He’s got such a strong point of view, which is translatable. But he’s so green that it’s hard. It’s a difficult year to be honest, to pick a winner. It boils down to what the criteria are for who should win. Should it be the people who would gain most from it, or should it be the people that have performed the best and therefore deserve to win it but might not need it as much as other people?”

Chromat models at the CVFF fashion show | Photo: Donato Sardella/Getty

The judges are looking for labels that will be here in five years time, not to carry someone for a season or two. “I often question, what does it even mean to be a designer anymore?” Gelinas comments just a few days before the end of the competition. “Are we building collections or building brands?”

“Who would benefit most from winning? Even that’s a hard thing to define,” Neville continues. “Benefiting most from winning meaning, ‘I’m not going out of business,’ or benefiting most from winning meaning, ‘I’m going to really be able to catapult myself?’ There are only a few companies that really have the infrastructure, the foundation, that this would help propel them forward.”

“I like this girl with the technology, Chromat. She’s incredibly talented,” von Fürstenberg says from her office in New York, fresh from her one-on-one studio visits with each designer. “Then you have [Brother Vellies] who is doing something completely sustainable. I think that’s so wonderful. They’re my favourite. At the end, everything exists in every colour, in every price. More than ever, talent and creativity is important. That is the truth.”

The Los Angeles festivities end with the Bouchon dinner, in a room filled with enough A-listers — including Reese Witherspoon and Lily Collins — to attract a swarm of paparazzi out front. Simkhai is seated between Collins and Wintour, which some consider a hint that the Vogue editor has decided on her own favourite. But while it’s easy to place bets, there is a genuine feeling that everyone who participates in the CVFF wins, even if only three will take away prizes in New York on Monday night.

West, who stands up to speak before the rib eye steak is served, makes a heartfelt attempt to sum it up himself. “There’s something about this competition,” he says. “Anna is still the most powerful person in fashion. I think we should applaud to that. To be in that position to help young designers to communicate with the masses, to break through, to use the mix of celebrity and designers, to keep pushing that conversation... to where we are now. I really think what [the designers] are doing is equally important as what the guys are doing in San Francisco, and D.C. [Fashion] is an important part of culture.”

Editor’s Note: This article was revised on 2 November, 2015. An earlier version of this article misstated that Baldwin is based in St. Louis. It is based in Kansas City. This article also misstated that Gypsy Sport was founded in 2006. It was founded in 2012.