Jackie ‘O’ Henderson is in her Meghan Markle era! Radio star swaps her edgy outfits for floaty floral dresses and refined ensembles ahead of Duchess’ appearance at her Best Life retreat

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Jackie Henderson and her business partner, Gemma O’Neill, are excited to announce that Meghan Markle will be the main speaker at their ‘Her Best Life’ retreat in Sydney next month.

In the weeks before the event, the radio personality seemed to be dressing like Meghan, Duchess of Sussex, wearing several outfits that looked similar to hers.

Jackie has recently shifted her style. While she used to be known for bold, attention-grabbing outfits – a look probably inspired by her fashionable friend Pip Edwards – she’s now opting for a more subtle and polished look.

She’s been seen wearing breezy floral dresses and soft, classic outfits – a style similar to the one Meghan Markle has favored since stepping down as a senior royal.

Jackie showed off her latest look on Wednesday when she went to her hairdresser in Bondi Beach. She was wearing a simple black top and a white, A-line midi skirt.

Jackie used to wear a lot of jewelry, but this time she kept it simple, choosing just a few plain gold bangles.

For shoes, she switched her once-loved high heels for practical brown sandals.  

She completed her look with an elegant black handbag. 

Just recently, Jackie was spotted in Newtown looking effortlessly bohemian and relaxed while leaving a sound frequency healing appointment.

For a casual outing, she chose a simple and sweet look, swapping her usual trendy clothes for a classic white babydoll dress with a delicate blue floral pattern.

Jackie paired this with a simple white canvas bag, two raw gemstone bracelets and brown sandals. 

I’ve been noticing a real shift in Jackie’s style lately – it’s so much more relaxed and chic. A perfect example? Back in February, I spotted her in Clovelly wearing this gorgeous, simple black maxi dress. It just felt so effortless and really highlighted her natural elegance.

Her pared-back look featured simple gold jewellery, a black handbag and brown slip-on sandals.

Jackie had previously embraced a ‘more is more’ mantra when it came to dressing. 

Last December, Jackie was photographed with her close friend Pip. She was wearing a bold T-shirt that said ‘Wrong party babe’ and paired it with stylish brown cargo pants.

In September, she showcased another stylish outfit while celebrating with friends, including Pip, at Icebergs in Bondi Beach.

She was wearing a brown button-down shirt, a very short matching skirt, and black pointed heels.

In Sydney during October, Jackie made a bold fashion statement, combining a delicate, embroidered white top with white cargo pants and brightly colored high heels.

Jackie and her business partner, Gemma O’Neill, are excited to announce that Meghan will be the main speaker at their ‘Her Best Life’ retreat in Sydney next month.

A three-day event for around 300 women will take place at the InterContinental Hotel in Coogee Beach, Sydney. The weekend will focus on building connections, improving wellbeing, and personal growth.

The April 17–19 event is anticipated to bring in nearly $1 million in ticket revenue.

VIP ticket holders, who pay $3,199, will get a group photo with the Duchess and will be seated in the first two rows at the gala dinner.

VIPs will also enjoy an exclusive goodie bag and a premium ocean-view hotel room. 

It was recently reported that Jackie chose not to host or interview Meghan, allowing Gemma to take the lead and get more attention.

On the latest episode of Her Best Life, Gemma revealed she strongly encouraged Jackie to lead the retreat, but Jackie declined.

She explained she tried to convince the other person to step in and manage the event, or at least take charge.

She was firm and told Gemma, “You have to do this for your own sake. It’s supposed to benefit you.”

Gemma explained that Jackie didn’t attend because she wanted to encourage Gemma to become more outgoing.

O’Neill explained that she understood he was reluctant and anxious, knowing he valued his privacy and generally disliked being put on the spot.

You prefer to work on the practical side of things and support projects from behind the scenes, rather than being the public face of them – I think many of you are aware of that.

I used to prefer keeping to myself, but now everything about my life is very public.

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2026-03-20 13:19