Jack Wills Wants to Forget its Posh Past, But Will it Work?

Once the must-have clothing for young toffs, the fashion brand is trying to become relatable by bringing in the TikTok stars.
The Jack Wills shop front in 2015, with a British flag
Image: Alamy

Picture the scene: A private jet full of influencers being served free champagne and sushi at 30,000, en route to a party villa in Ibiza. No, this wasn’t a Boohoo-sponsored press trip. It was for Jack Wills, the preppy-cool label better known for navy gilets, pale pink polo shirts and hoodies with ‘FABULOUSLY BRITISH’ written across the chest. Jack Wills, it transpires, is trying to forget its posh past. The question is: Will it succeed?


There was a time, between 2008 and 2016, when “dressing cool” for some teenagers meant owning a brand whose logo was a pheasant holding a cane and a top hat. In a 2011 interview with the Financial Times titled ‘Pretty, Posh and Profitable’, founder Peter Williams stated the original thinking behind the brand, which sold puffer gilets for almost £100: “I thought – what if I could create a brand that could bottle what being at a British university is all about and all the cool amazing stuff that goes with that?”

Oxford, Eton, St Andrews and Winchester – where many of the UK’s most expensive and prestigious schools and universities are located – were the sites of Jack Wills’ initial expansion. Every move played into its “University Outfitters” slogan, commodifying what it meant to be posh, white and privately educated in the 2010s.

Wearing one of their pastel-coloured rugby shirts became heavily correlated with having a double barrelled surname. But as the brand grew, it wasn’t just worn by young elites – students en masse bought into the dream, begging for the latest hoodies at Christmas.

Since then, the years have been harsh to the brand. It repeatedly failed to evolve and, in 2019, went into administration after it reported annual operating losses of £14.2m. It was quickly snapped up by Sports Direct CEO Mike Ashley. Now, you can now find Jack Wills on the rails with sportswear brands like Adidas and Nike at Sports Direct stores.


It’s a “far cry from where you would expect to see the old version of the brand,” notes Andy Barr, a trend expert, and the co-founder and CEO of digital agency 10 Yetis. “Now,” he says, “the race is on to distance the Jack Wills brand from its posh past, with new styles of clothing being launched, and influencer campaigns with British TikTokers to try and spread awareness of its new image and bring in new audiences.”

The brand’s recent attempt at rebranding comes after their “IT’S A VIBE” campaign, which came under serious fire online. One ad, plastered on the walls of the London underground featured a number of black models in a house party setting. After years of excluding people of colour from its image, the attempt to capitalise on black culture to revitalise the brand was viewed by many as suspicious.

In an opinion piece for The i about brands trying to align themselves with black culture, Charlene White wrote: “It was never a brand me and my mates bought into; it wasn’t for us, so why would we? But when we did venture into its shops out of curiosity, we were never there for very long, as staff would invariably make a point of making us feel uncomfortable within seconds of entering. We were university age by that point, so technically their target audience. But not all undergraduates are created equal.”


For its follow-up, Jack Wills took a different angle, flying out British and Irish TikTok stars on a private jet to the ‘Jack Wills Ibiza House’. Attendees included Grace Barry (2.2 million TikTok followers), Max Balegde (1.9 million), Moyo Ajibade (2.1 million), and Kate Elisabeth (500k).

“It was kind of like Love Island but with influencers,” says Chiara King (2.9 million), one of the creators invited on the trip. “It was literally like not being on planet Earth. We got on a private jet, we were all drinking champagne, we were getting pretty tipsy. You wouldn’t think Jack Wills is going to be spending that much budget on such a trip.” According to King, the creators were provided with only Jack Wills clothing. “I think the quality is better now,” she says, “the outfits are classic and a bit younger as well.”

When asked about Jack Wills’s elitist past, she pointed out that casting influencers and content creators creates a more diverse image than the models of the past – though, it’s worth noting that clothing on the Jack Wills website only goes up to a UK size 16. “The diversity was definitely there and I think by working with TikTokers, social media people, YouTubers – you know, we are just normal people, everyone comes from a totally different background.”

While TikTokers did share a vast amount of Jack Wills-related content during the trip, Barr points out that simply getting influencers to share content of themselves wearing the clothes may not be as successful as the brand hopes. “In my opinion, Jack Wills has gone too far with this one. Flashing the cash with a luxury mansion and a private jet to the British public – while many are experiencing high levels of financial difficulty due to the current cost of living crisis – is always going to leave a sour taste.”


King disagrees. “When we got the private jet,” she says, “I remember seeing a hate comment being like: ‘Oh it’s so bad for the environment using a private jet.’ But then again, those same people, if you asked them, ‘Do you wanna go on a private jet?’ – they wouldn’t say, ‘Oh no, but it’s bad for the environment.’ I think anyone in their right mind will say, ‘Yes please, thank you very much’.”

Gifting high-profile teens incredible perks in exchange for brand promotion isn’t that different from Jack Wills near history. Back in 2016, the brand ran a “Seasonnaires” campaign, in which they sent cherry-picked British students around the world as brand ambassadors. The Daily Mail described Ella Crockett, one of the chosen ambassadors, as the “student who was paid to party”.

Crockett was flown to America to spend a summer hitting up the most exclusive yacht parties and soirees, while documenting the experience on Instagram. She then joined the Jack Wills marketing team, before leaving the company in November 2018. “Now I don’t really identify with the brand as much,” she says. “It’s definitely going through a transition phase and changing from what it used to be… I think it’s always going to be hard to shake off that kind of stereotype that Jack Wills had.”

Will this rebrand work? The clothes may be different and the obvious links to elitism have been dropped, but flashy experiences that most can’t afford still seem to be at the heart of what it stands for. And during a time of economic downturn, that feels more tone deaf than ever. “I think Jack Wills needs to pause what they’re doing and take time to fully analyse the market,” Barr says. “Now, they seem to be digging themselves into a bigger hole than they’re going to be able to get out of.”