They started out aged 16 and 15 and went full-time instead of staying in education
A teenage couple who have pocketed more than £50,000 flipping vintage clothes seven days a week say their biggest motivation was avoiding student debt – and now they are saving for their first home with “no regrets”. Henry Howard and Holly Proud, from Bishop’s Stortford, Hertfordshire, began hunting for designer bargains and reselling clothes in 2023, aged just 16 and 15.
Within months, they said they were making around £2,000 a month and decided to pursue the business full-time rather than follow many of their friends to university. Holly, now 19, said the flexibility of self-employment has allowed her to continue working around her postural orthostatic tachycardia syndrome (POTS), a condition that causes a rapid increase in heart rate when standing up, often leading to dizziness and light-headedness.
After moving the business into a 1,000 square foot unit in 2025, the couple went on to score sales including a Yves Saint Laurent jacket bought for £20 and sold for £200, and a Juicy Couture handbag purchased for £10 and sold for £110.
Henry, now 20, told PA Real Life: “It’s been extremely rewarding. I’ve always believed this was something serious and that we could make it work.
“We’re enjoying ourselves, making a decent amount of money, and one of the biggest driving forces for me is that I’m not in debt like many of my peers who went to university. We’ve got no regrets about not going.”
Henry and Holly became a couple in June 2022 after meeting through mutual friends at secondary school. The pair began reselling clothes in January 2023, combining Henry’s interest in business with Holly’s background in fashion.
They started by buying “underpriced items” from charity shops, such as branded T-shirts, often doubling their money on each sale. The couple would even rummage through bargain bins, finding Ralph Lauren jumpers for as little as £2 and selling them for up to £30 on Vinted and Depop.
“We saw it as a way to get some extra pocket money for going out at first really, we couldn’t believe how cheap we could get some of the branded items in charity shops,” Henry said. After discovering they could buy vintage clothing in bulk online, via wholesaler Fleek, they realised it could become a viable business.
Henry said: “As we scaled up our orders, we scaled up the volume we were selling. We started out in Holly’s bedroom, then moved into her spare bedroom, then a room in my house, and eventually into her grandparents’ annex.”
By the summer, they were making around £2,000 a month. One of their early successes came when they bought a bundle of 50 Carhartt trousers for around £400 and sold each pair for £20. Henry and Holly then decided to pursue the business full-time, instead of going to university.
Henry said: “There was definitely some shock from people around me, as around 95% of my friends went to university. My school largely encouraged me to go to university and stay in education, but I was lucky to have a very supportive family.”
In 2023, Holly was diagnosed with POTS and she has found working for herself more accessible, allowing her to work flexible hours depending on how she is feeling.
She said: “Day to day, I definitely have to take things at my own pace and sit down more regularly. The heat makes it so much worse too. I don’t think I could have gone to university with it.”
In November 2025, the couple moved the business into a 1,000 square foot unit to maximise the amount of stock they could purchase.
Holly said: “We work well together as a team – Henry is good at the business and numbers side, and I have a lot of knowledge about fashion – we agree on most things!”
Since then, they have bought a vintage Valentino suit for £10 and sold it for £250. They also flipped a Yves Saint Laurent jacket bought for £20 for £200, while a Juicy Couture handbag purchased for £10 sold for £110. Another profitable find was a pair of Frye cowboy boots, which they bought for £15 and later sold for £135.
Holly said: “I think I’m quite good at knowing what’s trending, so we look for that as well as big brands – that’s what always works for us. I’m really passionate about the environment. If any of our clothes have holes in them, I sew them up or add patches to make them more unique before we sell them. We rarely buy ourselves anything new now.”
The couple work seven days a week, viewing the business as a combination of hobby and career, and now generate upwards of £2,000 a week in sales. In total, Henry said they have made around £50,000 so far.
While they have treated themselves to holidays, including a trip to Copenhagen, they are primarily focused on saving for their first home.
Holly said: “We’re just excited for the future and what’s to come, we want to just keep growing the business!”
To find out more, visit www.joinfleek.com
