When Season 1 of With Love, Meghan came out in March, the Daily Mail excitedly cataloged the cost of the Duchess of Sussex’s clothing worn in the series. And when I say “cataloged,” I mean they literally did a breakdown of every single item she wore in each episode and estimated the cost. They claimed, at the time, that Meghan was exhibiting a new “stealth wealth” sartorial vibe, but even stealth wealth doesn’t cut it for the pocket-watchers over there. Well, the Mail is probably waiting until Season 2 premieres next week to do another thorough breakdown of wardrobe costs. But they weren’t content to simply sit on their hands and wait! Of course not. They contacted a California stylist and “image consultant” to talk about Meghan’s Season 2 style. Just in case you didn’t get the Mail’s obsession from this week’s story about Meghan’s everyday jewelry.
Meghan Markle is sending a clear message in her new Netflix series, according to a style expert: She’s no longer a Duchess. According to California-based personal stylist and image consultant Cynthia Kennedy, Meghan is ‘not dressing like a Duchess anymore’ based on the outfits she donned in the teaser for season two of With Love, Meghan.
During the first season, Meghan showed off her ‘quiet luxury’ wardrobe of expensive but classically tailored staples from designer labels such as Loro Piana, Max Mara and Brunello Cucinelli. Some items – mostly cashmeres and linens in various shades of beige – were individually worth over $1,000.
But Kennedy told the Daily Mail that Meghan is clearly going for a rather different look when it comes to clothing in the upcoming second season. In the trailer, the Duchess can be seen wearing a loud striped dress, a floral frock, and a chunky crimson sweater – a far cry from the uniform tones and cuts of season one. Kennedy said that Meghan’s style on season two of her Netflix show is sending the audience a clear message that she doesn’t have to dress like ‘a Duchess anymore.’
‘Her revamped style is sending everyone a message that I don’t have to dress like a duchess anymore — I get to dress like myself, and be more approachable, modern, authentic and real,’ the expert shared. ‘Her choices feel deliberate and more like a conscious move toward comfort, vulnerability, relatability, and ease without losing that sense of polish that keeps her aspirational. It’s a careful balance and I think she’s hitting it.’
Kennedy, who is the CEO of Cynthia Kennedy Stylist, told the Daily Mail exclusively that there’s ‘definitely’ been a ‘shift’ in her style from season one to season two.
‘In season one, Meghan relied on very polished, put-together looks that were almost “Duchess-lite” – clean tailoring, muted neutrals, structured pieces, and an overall feeling of being carefully refined,’ Kennedy continued. ‘In season two, her style feels softer, relaxed, effortless, and more lived-in. Her looks are still elegant, but now it’s mixed with approachable pieces like relaxed, cozy knits, breezy dresses, and more casual silhouettes. It feels less like a public figure on a stage and more like a woman at home letting you into her world.’
With this new look comes a different approach for viewers, too: relatability.
‘Meghan has always been aware of the image she projects, and this more relaxed wardrobe seems intentional,’ Kennedy explained. ‘It signals that she’s not trying to perform “royalty” anymore, but instead connect with people as a modern woman, wife, and mother. The softer looks strip away some of that formality and lean into relatability in a way that feels warm, grounded, and human – which helps her connect with viewers.’
That was nowhere near as bad as I thought it would be. It was actually sort of neutral-to-positive? I mean, I think this woman is full of sh-t, but sure, Meghan’s got a different wardrobe in the second season and that’s certainly one interpretation of it. What people are choosing to forget is that… Meghan filmed this last year. She filmed the first two seasons back-to-back in a few months. It’s not like she was making some big point of “in Season 1, it’s all about stealth wealth, but in Season 2, it’s all about rejecting royalty!” Meghan is just… wearing pieces she likes, and probably wearing many of the styles in her own closet. Incidentally, do you think Meghan will finally update her ShopMy account when WLM comes out? She hasn’t added anything to her page in over three months.
Poster & promotional images courtesy of Netflix.
