Unveiling the Smart Strategy and Hidden Message in Karoline Leavitt’s Fashion Choices

Messaging for many of the men in Trump 2.0 has, at least in recent days, gone rather embarrassingly off the rails.

The principals involved have struggled to provide coherent explanations about how Atlantic editor Jeffrey Goldberg became unintentionally included in a confidential Signal chat group. This incident has highlighted the vulnerabilities of experienced individuals who should have acted more prudently.

Enter Karoline Leavitt to pick up the pieces of this PR nightmare.

At just 27 years old and a mother of one, the youngest White House Press Secretary is known for her articulate, confident, and assertive demeanor. She has proven herself to be one of the most resilient individuals to stand behind the iconic White House podium.

In her short two months in office, she has already displayed a fearless ability to engage in tough exchanges with journalists, surprising many seasoned professionals in Washington with her unwavering approach.

But like most of the women who populate Trumpworld (and let’s be honest – any world), this rising superstar in the MAGA ecosystem isn’t just judged on her performance – she’s judged on her clothes.

Too conservative, too boring, too expensive, too matronly, too flashy – all are accusations that have been leveled in recent weeks at Leavitt who is, by any measure, atypical of Generation Z.

Boxy blazers, boucle skirt suits and jersey minidresses, this is a wardrobe that is a world away from the couture creations worn by the Trump family itself.

Articulate, confident and fiery, this 27-year-old mother-of-one is not only the youngest White House Press Secretary to grace the iconic podium, she is the steeliest. (Pictured: Karoline Leavitt).

Boxy blazers, boucle skirt suits and jersey minidresses, this is a wardrobe that is a world away from the couture creations worn by the Trump family itself.

On a salary of $180,000 a year Leavitt could hardly hope to compete with the financial demands of First Lady Melania’s Dior-filled wardrobe, but she could certainly afford more aspirational, youthful choices.

Instead, the sixth woman to hold the position since 2017 seems to have willfully ignored the examples of her predecessors (both on the Right and Left).

Eschewing the model-like propensities of Kayleigh McEnany, Leavitt has maintained a cautious and controlled formality – even frumpiness.

Her look is as far removed from her former boss (Leavitt worked as McEnany’s assistant in the first Trump administration) as it is from the kaleidoscope of colors and striking silhouettes that were a constant in the reigns of her Democratic forbearers Jen Psaki and Karine Jean-Pierre.

And it’s all because Leavitt is a woman who has quickly recognized that the most powerful backdrop for a forceful message is an outfit that seems to say nothing at all.

Finding her niche in styles which have ensured her words, rather than her wardrobe, do the talking, Leavitt has – like Hillary Clinton, Kamala Harris, and current White House Chief of Staff Susie Wiles – come to appreciate the value of a non-descript pantsuit.

Stepping up to the lectern for her very first press briefing, she chose a $109 purple blazer from Zara and coordinating $49.90 trousers that felt more schoolteacher than political powerhouse.

Her black patent and rhinestone-studded Jimmy Choo pumps might have added a touch of youthful pizzaz to the conservative ensemble had it not been for the unusually large diamond cross that hung around her neck.

It was an unmissable and rather ostentatious reminder that Leavitt’s star rose as a conservative firebrand at the Benedictine liberal arts college, Saint Anselm, in Goffstown, New Hampshire which she attended on a softball scholarship.

Her passionate op-eds in the college newspaper defending the 2017 Trump travel ban paved the way for her political future and marked her out as curiously regressive amongst an overwhelmingly progressive majority.

On a salary of $180,000 a year Leavitt could hardly hope to compete with the financial demands of Melania’s Dior-filled wardrobe, but she could certainly afford more aspirational, youthful choices.

Eschewing the model-like propensities of Kayleigh McEnany (pictured), Leavitt has maintained a cautious and controlled formality – even frumpiness.

Leavitt’s look is as far removed from her former boss (she worked as McEnany’s assistant in the previous administration) as it is from the kaleidoscope of colors and striking silhouettes that were a constant in the reigns of her Democratic forbearers Jen Psaki and Karine Jean-Pierre.

Leavitt has chosen to extend this winning formula through dress and has fully (and, I think, strategically) embraced a persona that is seemingly out of step with her generation and position.

Married to a man thirty-two years her senior and mother to an eight-month baby son, Leavitt is a full-on ‘trad wife’, except for the fact that she occupies one of the most powerful roles in American political life.

Resisting the urge to use the podium as a catwalk, Leavitt has astutely understood that her success lies in silhouettes that seem more appropriate to a woman approaching middle age than one on the verge of thirty.

While opting in for full ‘Republic glam’ – glossy blond hair and skin smoother than her baby’s bottom – and save for the occasional Louis Vuitton handbag or black leather dress (Super Bowl 2025), she has resisted the informality or unrestrained theatrics in which so many celebrities of her age indulge.

Indeed, what might pass as her most fashion forward moments have been a series of shimmery boucle dresses from the British brand Self-Portrait.

At first glance depressingly bland, it’s tempting see this choice of a brand once favored by the Princess of Wales as a courtly nod to the monarchical aspirations voiced by her presidential boss.

However conservative Leavitt’s dress sense she is, I believe, an enthusiastic innovator who has learned the lessons of her generation’s social media moment. 

But however conservative Leavitt’s dress sense she is, I believe, an enthusiastic innovator who has learned the lessons of her generation’s social media moment.

Unapologetic in her treatment of the traditional media outlets she dislikes, Leavitt has welcomed reporters from ‘new media.’

A catchall description for influencers and podcasters, this group have now been allocated front-row briefing room seats that were previously reserved for White House staff.

Leavitt has used their presence just as powerfully as her microphone to champion a thus far winning political narrative – and largely because she has defied her critics to become one of the most effective exponents of the new administration.

Leavitt has disguised her ingenuity in an unremarkable wardrobe, making her Trump’s not-so-secret weapon who hides her power in plain sight.