In the early 1900s, bright rugby shirts, cashmere sweaters and flannel blazers became a thing, with guys at prestigious US universities adopting the style of wealthy preparatory – or ‘prep’ – school students as a status symbol. The look remained a sign of privilege until the fifties, when the trend expanded thanks to the rise of Tommy Hilfiger, Calvin Klein and Lacoste, which started making these kinds of clothes for the masses.
Prep had never been more popular, having the final say on menswear for the next three decades and seeming like it might do so forever. But when streetwear came along, prepster brands were almost completely left behind. Streetwear evolved from the uniform of skaters, punks and hip-hop heads into a $185bn industry that accounts for around 10% of the entire global apparel and footwear market, according to the consulting and accountancy firm PwC.
It’s been a good few years since modern prepster brands have dominated fashion, but a self-described ‘menswear nerd’ is leading a mashup that nobody knew they wanted – preppy streetwear – and achieving a level of success that’s increasingly uncommon in an otherwise badly struggling industry.
Yet on the face of it, Rowing Blazers is about as far away from Supreme, Off-White and all the others as you can get. It might sell ‘preppy’-looking clothes, but the business model underpinning the brand is straight out of the streetwear playbook. ‘I wouldn’t say that Rowing Blazers is a streetwear brand,’ says CEO Jack Carlson. ‘Although we’ve been called a streetwear brand before, it’s sort of funny to me. I think it’s most likely because I am a fan of streetwear personally, so I consciously or subconsciously channel some of the philosophies and ideas.’
‘Although we’ve been called a streetwear brand before, it’s sort of funny to me. I think it’s most likely because I am a fan of streetwear personally, so I consciously or subconsciously channel some of the philosophies and ideas.’
Rowing Blazers undoubtedly speaks the language of streetwear. Drops often happen on Thursdays, the brand’s campaigns have always featured multiracial casts, there’s a strong sense of irony and subversion and there are too many collaborations to keep up with. In many ways, the brand today has more in common creatively with urban youth subculture than it does with prep. You are as likely to see the Winklevoss twins wearing Rowing Blazers as you are on someone queuing up for the latest Supreme drop.
Rowing Blazers’ long list of past collabs – from FILA, Slim Aarons and Barbour to streetwear brands such as Noah – shows how highly the brand is regarded by the rest of the fashion industry. Still, says Jack, ‘We’ve had big brands offering us a lot of money to do collaborations with them, but often we turn them down if I feel that it’s going to have a negative impact. No amount of money can buy your reputation back.’
The early days
Describing his decision to start the brand in 2017 and concentrate his designs around the most Ivy League of items, the rower’s blazer, Jack says, ‘Friends of mine were literally begging me not to do it. They were convinced that the [streetwear-dominated] moment we were in was a million miles away from, well, blazers.’
Even now, the data suggests his friends were right. In May 2020, J Crew, the 73-year-old retailer whose new millennium- style take was hugely popular with American consumers, filed for bankruptcy. Two months later, another major prepster brand, Brooks Brothers, left behind $600m in debts.
But as with so many of the most successful counter-cultural brands, Jack didn’t launch Rowing Blazers with the sole aim of making good money. He started the brand because he was passionate about an aesthetic he wanted to revive. ‘I grew up between Boston and London, but I always spent my summers in Hampstead and it gave me this love not just of the architecture, fashions and design, but more importantly of the history,’ he explains. ‘I was always interested in heraldry and, more broadly, the meaning behind traditions.’
Jack was even an intern at the College of Arms, the British institution that designs new coats of arms, and later went into academia to read archaeology. During this time, first as an undergraduate at Georgetown and later studying for a Doctor of Philosophy at Brasenose College, Oxford, Jack was also introduced to rowing – a sport unlike any other, with ties to academic institutions and their ancient, often elitist traditions.
Between 2011 and 2015, Jack went from being an amateur rower to representing the US at three World Championships. He also raced at the Henley Royal Regatta, an annual rowing competition established in 1839 and held on the same quintessentially English straight of the River Thames that served as the setting for Kenneth Grahame’s 1908 children’s classic The Wind in the Willows.
‘Henley is like Wimbledon tennis but for rowing,’ Jack says, recalling his past triumphs. ‘Once, though, we got knocked out in the first round – pretty disappointing having come all the way from America. But it did mean I was able to spend time in the Stewards’ Enclosure where there was a strict dress code, with crews each wearing unique, colourful blazers.
‘I was immediately fascinated by them, asking everyone what you do to earn them and hearing these quirky stories about the myths associated with them,’ Jack continues. ‘Everything from Dutch rowers whose blazers were ripped to shreds or missing sleeves because they have an organised fight to earn it, to this one British club that rips down a clubhouse curtain and makes it into a blazer if a rower wins three races. I thought someone should make a coffee table book about it all.’
And so, in 2017, he did. Although he thought it would only interest the rowing community, the book also resonated with menswear fashion communities – including Ralph Lauren, who hosted a series of events for the book leading to a lot of personal publicity for Jack.
‘I started receiving emails from rowers asking me if I could make blazers for them,’ Jack says. ‘At first I had to tell them that I was actually an archaeologist, but then I started looking into the cottage industry of tailors who were making these blazers, usually just one local tailor who would be taking all the knowledge away with them if they retired. Many of the rowing clubs I photographed for the book hadn’t gotten new blazers made in years.
When Jack finally decided to start Rowing Blazers, he didn’t employ any designers at first. Instead, he collected vintage blazers and reverse engineered them. ‘Eventually we got it pretty much exactly right using all the old techniques and stitching,’ he says. ‘But we also updated them a little bit so that the fit didn’t look like you were wearing something from the twenties.’
Soon the brand was making blazers for elite rowing clubs. ‘We hadn’t even made a website at the time but we were already full steam ahead,’ says Jack. But by 2020, Rowing Blazers had moved on from its purist roots. When asked about the ‘prep revival’, Jack replies: ‘I hate the “p” word. It has so many negative connotations. When we launched, the very first article published about us had a headline something like: “Former US rower Jack Carlson launches uber-preppy brand”, and I was like, “Oh, God, we’re going to have an uphill battle, aren’t we?”
‘What we do has a sense of irony, but also a reverence for the past,’ he continues. ‘We aren’t too stuffy. We want to be accessible. Over the past three years, I think we’ve done well to redefine the “p” word.’
‘I started receiving emails from rowers asking me if I could make blazers for them. At first I had to tell them that I was actually an archaeologist, but then I started looking into the industry... Many of the rowing clubs I photographed for the book hadn’t gotten new blazers made in years.’
While the US remains Rowing Blazers’ biggest market, it is also popular internationally, especially in Japan, Korea, Australia and northern Europe. And although Rowing Blazers has a store – or ‘clubhouse’ as the brand unironically calls it – in SoHo, New York City, and has held pop-ups in various countries, the majority of its sales come from online. At a time when the retail industry is straining, with menswear sales falling by more than 15% throughout 2020, according to Euromonitor, Rowing Blazers’ unusual brand positioning somewhere between prep and streetwear has been proving popular. In 2020, Jack estimates his company will have turned over around $8m.
As well as its profit margins, Rowing Blazers’ team is also growing. Last year Web Smith, founder and editor-in-chief of 2PM Inc, and Edith Young, former associate editor at Man Repeller, both joined the company in senior roles, bringing yet more streetwear credentials to the brand.
Covid-19 wasn’t the only major issue Rowing Blazers had to contend with last year. The brand also took a particularly strong stance on supporting the Black Lives Matter movement. Part of rebranding the ‘p’ word is paying tribute to the black and minority prep fashion influences that made streetwear- prep possible. For two weeks over the summer, Jack donated 100% of Rowing Blazers’ proceeds to the NAACP. Acknowledging that both prep fashion and the sports and academic worlds that inspired it were ‘predominantly white’ and frequently inaccessible to communities of colour, Jack has also helped to fund and promote causes that help to break down the barriers of entry into rowing in particular.
Rowing Blazers makes regular donations and carries out partnerships with Row New York, a not-for-profit that aims to help members of the black community get into rowing and the academic privileges it can offer as well.
‘When I first heard about it, I thought: “Oh, that’s nice, they get these kids out on the water, show them what rowing is,”’ says Jack. ‘But it’s actually a very competitive programme, with kids who’ll win the New York State Championships meeting all these private schools along the way. Close up, you can really see how huge opening a few doors can be to someone.’
This article was first published in Courier issue 39, February/March 2021. To purchase the issue or become a subscriber, head to our webshop.