Inside Jackie ‘O’ Henderson’s lavish lifestyle including a VERY glamorous celebrity dog walker as she walks away from $100million radio contract and The Kyle & Jackie O Show

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Jackie ‘O’ Henderson recently turned down a lucrative $100 million radio deal, but she’s still expected to maintain her comfortable lifestyle.

After a highly successful and profitable run, radio personality Kyle Sandilands, 51, has ended his partnership with co-host Kyle & Jackie O on Tuesday.

The media personality is well-prepared for the next phase of her long career, having invested in a lavish lifestyle that includes a $30 million home, a sports car, designer clothes, luxurious vacations, and even a dedicated dog walker.

The most valuable property in Henderson’s investment collection is the $13.25 million oceanfront home in Clovelly she bought last year.

Jackie is completely renovating her home in a highly desirable Australian location, with the project costing around $5 million.

Although the amount she spent on the house is significant, the improvements she’s making could ultimately earn her a substantial profit on her investment.

Oh my gosh, you guys, the house is STILL being built, but the artist’s renderings? They’re EVERYTHING! It’s going to be this incredible, multi-level mansion, and the views… seriously, unobstructed ocean views right over Gordons Bay! And get this – the gym literally opens up to the pool! I’m already planning how I’ll spend all my time there. It’s going to be absolute heaven!

Architect Madeleine Blanchfield designed the four-bedroom house to fulfill Jackie’s dream of creating a space that feels like being on the Amalfi Coast in Italy for guests.

Once the renovations are finished, the house is predicted to be worth around $30 million. Jackie is currently staying in a rental property with her daughter, Kitty, while dealing with media attention following her exit from The Kyle & Jackie O Show.

I’ve been following the news, and it’s interesting to see how even the smallest details of her life are being reported! Apparently, she recently hired a dog walker for Sadie, her adorable Cavoodle who she welcomed into the family last year.

A stylish woman was seen leaving the radio personality’s home walking her dog. She was wearing a black tank top, short shorts, and fashionable boots.

She wore a cap and sunglasses to shield her face, and added a trendy bum bag around her waist.

When Jackie isn’t relaxing at home, she’s often driving around town in her expensive, black Range Rover Sport, valued at around $500,000.

The celebrity radio host bought the car in 2024, and revealed she was able to get it quickly because it was initially brought into the country for another person.

Unfortunately, the person who was supposed to receive the car ended up in jail and couldn’t take possession of it, so Jackie unexpectedly became the new owner.

Jackie has also proven she’s not shy about splashing thousands on opulent holidays. 

Just before signing her groundbreaking $100 million, 10-year deal with KIIS FM and Kyle Sandilands, the mother of one took a three-week vacation to Europe with her daughter, Kitty.

A mother and daughter enjoyed a lavish trip to Paris, the south of France, and the Amalfi Coast, posting stunning photos of their adventures – including sights like the Eiffel Tower and the French Riviera.

Around the same period, Jackie spent time working and vacationing in Positano and St-Tropez, using rented villas as temporary broadcast locations.

That same year, Jackie had a fun-filled summer in Western Australia with her close friend and manager, Gemma O’Neill. They spent time at Ningaloo Reef, enjoying a beach vacation and even swimming with whale sharks.

To ring in the New Year and celebrate her daughter Kitty’s thirteenth birthday, the radio host spent the holidays at a luxurious resort on Kokomo Private Island in Fiji.

Jackie spent a surprising $11,000 a week to treat her teenage daughter to a luxurious resort vacation.

She didn’t travel much in 2024, but she took two big trips in June and December, plus a quick work trip to New York.

She started with a trip abroad with her close friend, Gemma, flying to Mykonos. There, they enjoyed the lively beach clubs and stayed at the luxurious Soho Roc House.

To finish off their amazing trip, they headed to the UK and booked a hotel close to the Glastonbury Festival. It was the perfect way to experience a bit of British culture and soak up the festival vibes, even if they weren’t actually attending! As a travel tip, staying near popular events can really add a fun dimension to your holiday.

Later that year, Jackie traveled internationally again, this time with her daughter Kitty to the Phi Phi Islands in Thailand for a relaxing vacation.

Social media posts revealed the group enjoying boat rides and paddleboarding, having fun near the beach.

Jackie spent last year’s Easter holiday much like this one, traveling to Tuscany and Lake Como with Kitty.

They stayed at the opulent Passalacqua hotel, where rooms start at around $2,500 per night. 

Kitty and her famous mother spent their days cycling through Tuscan countryside and sightseeing. 

Just a few months later, Jackie returned to Kokomo Private Island Resort in Fiji, a place she clearly loves. She was seen relaxing on a catamaran by the sea.

Perhaps one of Jackie’s most exuberant displays of wealth is her ever-growing designer wardrobe.

Let me tell you, 2023 was a big year for me – I lost 18kg and completely revamped my style! It wasn’t just about the weight loss, though; I really wanted a whole new look and feel. I worked with the amazing Jess Pecoraro, one of Australia’s top stylists, and she helped me create an aesthetic that truly feels like me.

Sydney fashion stylist has worked with many well-known Australian personalities, including Jesinta Franklin, Zoe Foster Blake, Georgia Fowler, Delta Goodrem, and Pip Edwards, among others.

Jackie is often seen out and about, whether she’s doing everyday tasks or going to glamorous parties, and she always looks fashionable in expensive designer clothes.

She’s known for her expensive style, and recently wore a $595 Christopher Esber T-shirt with a $495 mini-skirt to celebrate her 49th birthday in 2024.

Also that year, she was seen shopping at the high-end Désordre boutique in Darlinghurst.

Jackie has a Prada cotton bomber jacket worth $6,600, and she also owns a $2,950 dress and a $2,650 miniskirt from the same designer.

While Jackie often wears Prada and Christopher Esber, Zimmerman seems to be her favorite designer.

As a style enthusiast, I’ve noticed she frequently wears beautiful, flowing floral dresses from this designer. They’re definitely an investment piece – I’ve seen them range from around $795 for a gorgeous piece called the Waverly, all the way up to $4,288 for a stunning blue silk linen organza design. It’s clear she appreciates quality and timeless style!

Even her most basic clothing items are expensive; for example, a simple white T-shirt she wore costs $397.

However, the most lavish items in Jackie’s wardrobe are her designer accessories. 

We don’t know exactly how large her collection is, but it seems to include expensive pieces from designers like Yves Saint Laurent, Prada, Bottega Veneta, and Miu Miu.

She’s been spotted carrying a $3,300 YSL handbag and a $5,450 tote bag from the same designer.

She showcased her wealth in 2024 when she wore a $12,000 outfit to a party in Rose Bay, which included $1,830 Prada loafers and $895 Bottega Veneta sunglasses.

Let’s talk accessories! I’ve noticed she’s often spotted with a gorgeous Miu Miu bag – it’s one of those smaller, super-soft leather hobos, and honestly, it’s a bit of a splurge at around $3,100. It’s definitely a statement piece!

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2026-03-06 14:05