Jackie ‘O’ Henderson may have just walked away from a $100million radio contract, but it doesn’t look like her luxury lifestyle is going to take much of a hit.
The radio star, 51, called time on The Kyle & Jackie O Show and her co-star Kyle Sandilands on Tuesday after a very successful and lucrative partnership.
From a $30million mansion and sports car to a designer wardrobe, no-expense-spared holidays and a hot dog walker on call, the media personality has more than prepared for what comes next in her decades-long career.
Henderson’s most lucrative asset in her portfolio is the $13.25million Clovelly oceanfront property she purchased in 2023.
Situated in one of the most sought-after locations in Australia, Jackie is currently doing an entire rebuild of the home, to the tune of a whopping $5million.
But while the cash she has splashed on the house is nothing to balk at, it’s the value she’s adding to the property that could earn her back the investment with a hefty profit.
While the Clovelly home remains under construction, artist impressions have shown the house will boast a multi-level mansion with uninterrupted ocean views across Gordons Bay and a gym that opens up to a pool.
Plans for the four–bedroom abode were designed by architect Madeleine Blanchfield, with Jackie’s vision set to make guests feel like they ‘are in Italy on the Amalfi Coast’.
The home is expected to be worth an eye-watering $30 million when the rebuild is complete, with Jackie currently hiding out in a rental with her daughter Kitty as she weathers the media storm of her recent departure from The Kyle & Jackie O Show.
Just recently, on Thursday, it was even noted she had hired a dog walker to come around and take out her Cavoodle, which she purchased and named Sadie in 2023.
The woman – who was notably very chic – was spotted exiting the radio star’s property with lead in hand, dressed in a black tank top and mini shorts paired with stylish boots.
She kept her face covered with a cap and stylish sunglasses as she strapped a bum bag around her hips.
When she’s not living it up at home, Jackie can be seen cruising around town in her luxury, all-black Range Rover Sport, which is worth about $500,000.
The radio star purchased the vehicle in 2024, admitting at the time that she was able to bypass the huge wait period for the vehicle because it had originally been imported into the country for someone else.
However, the intended owner was sent to jail ‘and could no longer pick it up’, leaving Jackie the lucky owner of the brand-new car.
Jackie has also proven she’s not shy about splashing thousands on opulent holidays.
Not long before she signed her historic $100million, 10-year contract with KIIS FM and co-host Sandilands, the mother-of-one embarked on a three-week Europe holiday with her daughter Kitty.
The mother-daughter duo spared no expense as they swanned about Paris, the south of France and the Amalfi Coast – sharing enviable photos of everything from the Eiffel Tower to the Riviera.
Around the same time, Jackie also enjoyed a working holiday in Positano and St-Tropez, renting villas in the area to broadcast from.
The same year, Jackie went on to enjoy a ‘hot girl summer’ with her best friend and manager Gemma O’Neill in Western Australia, with the pair visiting Ningaloo Reef for a beach holiday where they swam with whale sharks.
The radio host finished off 2023 and brought in the New Year by taking her daughter Kitty to a luxury resort on Kokomo Private Island in Fiji to celebrate her 13th birthday.
Jackie spoiled her teenage daughter with a lavish resort that set her back a shocking $11,000 per week.
The blonde beauty kept her travel to a minimum in 2024, but did enjoy two massive trips in June and December, as well as a brief trip to New York for work.
She began with an international trip with her ‘bestie’ Gemma, jetting off to Mykonos where they let loose in beach clubs and stayed at the ritzy Soho Roc House.
They then rounded their holiday out with a visit to the UK, where they stayed at a hotel near the Glastonbury Festival.
Jackie did another international trip later in the year, again with her daughter Kitty, but stayed closer to home as the pair enjoyed a getaway to the Phi Phi Islands in Thailand.
Posts shared to social media showed them partaking in boat rides and paddleboarding as they lived it up near the beach.
Last year was spent in a similar fashion, with Jackie spending the Easter break in 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 made her way back to Kokomo Private Island Resort in Fiji – a clear favourite as she was spotted languishing at the seaside escape on a catamaran.
Perhaps one of Jackie’s most exuberant displays of wealth is her ever-growing designer wardrobe.
Since shedding 18kg in 2023, the blonde beauty has undergone a complete transformation of not only her look – but her aesthetic as well – largely thanks to one of Australia’s most in-demand stylists, Jess Pecoraro.
The Sydney-based celebrity fashion stylist has dressed some of Australia’s biggest names, including AFL WAG Jesinta Franklin, Zoe-Foster Blake, model Georgia Fowler, singer Delta Goodrem and P.E Nation co-founder Pip Edwards to name a few.
Jackie is frequently spotted running errands and attending ritzy events while wearing the most stylish designer clothes money can buy.
To date, she has been seen in a myriad of expensive outfits, including a $595 Christopher Esber T-shirt and a matching micro mini-skirt worth $495 for her 49th birthday in 2024.
That same year she was also spotted enjoying a shopping spree at designer boutique Désordre in Darlinghurst.
Jackie also owns a cotton bomber jacket from Prada, valued at a whopping $6,600, and a short dress ($2,950) from the same design house, as well as a Gabardine miniskirt worth $2,650.
Jackie is frequently spotted running errands and attending ritzy events while wearing the most stylish designer clothes money can buy
Prada and Christopher Esber make regular appearances in her wardrobe, but Zimmerman appears to be the go-to for Jackie.
She has often been seen in flowing floral patterned dresses from the brand, ranging from $795 for her Waverly number right up to $4,288 for a blue silk linen organza designed by the label.
Even her basics are on the costly side, as she has been seen swanning around in a simple white T-shirt which retails for $397.
However, the most lavish items in Jackie’s wardrobe are her designer accessories.
While the breadth of her collection is currently unknown, there are hints her shelves are filled with pricey items from Yves Saint Laurent, Prada, Bottega Veneta and Miu Miu.
She has been seen toting a YSL handbag worth $3,300, and a tote from the same fashion house valued at $5,450.
In 2024, she flaunted her wealth when she stepped out in a $12,000 outfit to attend a Rose Bay party – white leather loafers by Prada ($1,830) and Bottega Veneta aviator sunglasses ($895) were included in her look.
She has also been known to carry around a Miu Miu Wander matelassé nappa leather hobo mini–bag worth an eye-watering $3,100.
cre: Dailymail