Boujie dinners and girls’ nights out: Inside Jessie’s adventure-filled life before Love Island

She’s now living with Will on the farm🥺


Jessie and Will may not have won Love Island, but they have won the hearts of the public with their adorable TikTok videos since leaving the villa. Despite a few bumps in the road while they were on the show, Jessie and Will have been nothing but couples goals since the show ended.

Jessie is now living and working on Will’s farm, a major change from her life in Australia. But just how different? Jessie was already on Love Island Australia before starring on the UK show, and so was living her influencer life well before any of her fellow Islanders. Here’s everything you need to know about Love Island’s Jessie Wynter’s life before she was a bombshell on the show.

Jessie was a finalist on Miss Universe Australia

Love Island's Jessie Wynter's life

via Instagram @jessiereneewynter

In 2019, Jess competed in Miss Universe Australia and although she didn’t win the competition, she went far and managed to get to the final. If you scroll far back enough on Jessie’s Instagram, Jessie shared a load of photos of her time competing, all before she went on Love Island Australia for the first time.

Jessie has opened up about her Miss Universe experience, and speaking to 9Now, she revealed the secret to going far is down to your personality. She said: “The key thing I learned in Miss Universe Australia is it’s actually not looks-orientated. It’s all about what you bring with your personality.

“When I walked out on that stage in a bikini, no one was looking at all the little flaws. I could see they were looking at my facial expression, like am I enjoying it? Am I engaging with the crowd? That’s what people are looking for. like it’s all your personality. It’s not about all looks. It’s about what you got on the inside.”

She is a personal trainer and loves going on adventures

Love Island's Jessie Wynter's life

via Instagram @jessiereneewynter

Jessie introduced herself as a personal trainer when she entered the Love Island villa, and her fitness knowledge proved a success during movie night. A lot Jessie’s Instagram is full of her on the most scenic walks, in and around Australia.

Whether she’s at a beach, a waterfall or a national park, Jessie is always up to something exciting. Jessie is originally from Tasmania, an island state of Australia situated just off the mainland. In one Instagram post from September 2022, Jessie shared the most gorgeous views of Kingston Beach in Tasmania, and said: “Wholesome mornings with a spontaneous dip in the ocean.”

She is an avid traveller

Love Island's Jessie Wynter's life

via Instagram @jessiereneewynter

Like a lot of her fellow Islanders, Jessie loves a holiday and has frequently jet set to the UK and Channel Islands. In a few of her posts, Jessie has shared with her followers holidays to England, Jersey and Mallorca. When she was in London, Jessie told her followers how much she “loved” being there and what a “beautiful” city it is.

In April 2022, Jessie visited Jersey in the Channel Islands and even met up with former Islander Shannon Singh. It seems the pair were on a work trip together, but they wouldn’t be the first pair of cross-season Islanders who know each other.

via Instagram @jessiereneewynter

Jessie is always down for a night out

via Instagram @jessiereneewynter

The 26-year-old sure knows how to have fun, in the very best outfits. A lot of Jessie’s Instagram photos are of her on nights out with her friends or at fancy restaurants. Jessie often goes on dinner dates and nights out with her friends she truly has some of the best girl friendships. Her Instagram radiates pure positive vibes, and she brings exactly that to the South African villa.

via Instagram @jessiereneewynter

She looked completely different on Love Island Australia

via Instagram @jessiereneewynter

Love Island’s Jessie Wynter’s life was completely different before she made her debut on the Australian version of the show, with a completely different look.

Jessie made her Love Island debut on the Australian version of the show back in 2019 and she made it all the way to the final and left with a boyfriend, but they split up just months after the show. She was in a fair few couples while on the show, and split up with her first partner in the villa because she felt he was “seeking publicity”. Jessie was completely blonde while on Love Island Australia but has since embraced being a brunette.

Love Island 2023 continues at 9pm on ITV2 and ITVX. For all the latest Love Island news and gossip and for the best memes and quizzes, like The Holy Church of Love Island on Facebook.

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Featured image credit via Instagram @jessiereneewynter.

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