Meet the London-based Illustrator Who Turned Hobby to Hustle


Jennifer Darr is no starving artist.

“If you could do anything, what would you be?”

Before Jennifer Darr became the successful freelance artist behind Jen and Jennifer (you might recognise her illustrated celebrity portraits in Lisa Messenger’s new book, Purpose), the former fashion designer contemplated this question as she found herself jobless in London. It was unplanned; Jennifer and her new husband had left their home in Brisbane to travel around Europe for a few months, and like many Aussies, fell in love with that side of the world. They decided to stay, and her husband scored a well-paid job in London that enabled her to take time out.

“I was so incredibly lucky,” Jennifer says of the unintended sabbatical. When the couple sat down to work out what she should do, if she could do anything at all, the answer came easily: “I’ve always been an artist, but maybe not looked at it as a realistic job. It was a bit like, ‘That’s a bit fruity and I’m going to be a starving artist’.”

“My husband, who is obviously my No.1 supporter, was just like, ‘You can do it. We can give it a go for a few months,’” Jennifer says. So rather than overwhelming herself with the massive career shift ahead, she decided to take it one step at a time. “I think travelling taught us to do that. You don’t think about travelling all of Europe; you think about where you’re going tomorrow… I think when you focus your attention on one thing, if you really do put your heart into it, good things happen.”

The opportunity for the career change came at the perfect time, at what Jennifer calls her “quarter-life crisis”. At 26, fashion design wasn’t the fulfilling work she’d hoped. “My favourite part of the job was the creativity and having a product at the end, something that I felt like I’d created with my hands. And I guess what’s hard in fashion design, especially working within a big company, is that the name of the label gets the recognition,” Jennifer says. “I felt like I only had a very small part [of the creative process], whereas I really wanted to have something that I could say, ‘This is mine’, and be really proud.”

With nothing to lose, she started illustrating for a London boutique that sold pre-loved designer clothes. “That was the niche I first stumbled into. It’s great because it involved fashion and illustration. From there I just got requests and I started doing invitations for fashion events, and that kind of thing. I still look back and think I’m so incredibly lucky that it all happened the way it did.”

Four years on – including a stint living in Melbourne, and most recently, relocating back to London – Jennifer isn’t living any starving artist cliché, but is running a successful freelance business and a popular Instagram account. She mostly illustrates portraits and fashion with pen and ink, and has started playing around with watercolours. Now that she’s back in London, “The dream, obviously, is to one day do a sketch for Chanel or Dior.”

She says of her art: “I don’t necessarily want my work to be a political message or have a heavy meaning behind it. I want it to be something that people enjoy. And even if it’s just for a moment they’re scrolling by [on Instagram], if it makes them pause and think happy thoughts.

“The world is really a harsh place at the moment and I like the idea that I’m putting something nice or something beautiful, rather than adding negatively charged energy or bad feelings out there. All we can do is make sure our little pocket is a nice place. And I guess putting up art is my way of doing that.”


Pick up a copy of Lisa Messenger’s new book, Purpose, with illustrations by Jennifer Darr, here.

Lizza is a Sydney-based journalist and boxer.


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