Trump’s White House Press Secretary Karoline Leavitt probably didn’t expect her latest Instagram post to spark a fashion firestorm. What was meant to be a harmless behind-the-scenes glimpse into her professional life quickly turned into a full-blown social media debate.
The online conversation had little to do with her policy work — most of the noise was about her pink tweed outfit.
Leavitt, 27, is the youngest person ever to serve as White House Press Secretary. Yet, despite her age and generational ties to Gen Z, she’s being called out for fashion choices some say make her look decades older.
Her recent post, which shows her confidently walking into the White House in a hot pink tweed dress and matching shoes, reignited a recurring conversation about whether her style reflects personal taste or the influence of her relationships and surroundings.
The people in the comments didn’t hold back.
“Ahh look another grandma outfit for her old man!” one person commented, taking a jab at her 60-year-old husband.
Another joked, “Go take care of your Grandpa…sorry I meant your sugar daddy.” A third wrote, “27 pushing 68.”
The feedback kept pouring in, with one observer posting, “My mom is 80 and has that dress Karoline,” while another summed it up: “It’s giving grandma.”
Some even criticized how she walked writing, “Walking in like a BOSS!!” while others said, “I just tripped looking at her spacing of her walk MAGA.”
“She doesn’t rock that outfit like a grandma though… very cool outfit,” wrote one defender.
The criticism didn’t come out of nowhere.
Leavitt’s visual evolution has been drastic — and very public. A resurfaced photo from her pre-Washington days has now gone viral, with fans and critics alike questioning whether they’re looking at the same person who now commands the White House briefing room.
The image, showing a carefree then-25-year-old at a basketball game, has sparked intense debate about transformation, authenticity, and the pressures of political stardom.
She originally posted the image on Instagram on May 27, 2023, during Game 6 of the Boston Celtics versus Miami Heat Eastern Conference Finals at the Kaseya Center in Miami. The Celtics won that night by just one point — 104 to 103 — with a buzzer-beater that saved them from elimination. (The Celtics subsequently lost Game 7 at home.)
But Leavitt wasn’t the story then — her outfit is now. Standing in a suite overlooking the arena, she wore white jeans, a bright green tank top, sandals, and carried a small cork purse. Her blond hair hung straight, her skin noticeably sun-kissed. It was Miami in full effect.
That beachside, laid-back version of Leavitt now feels miles away from the polished, monochromatic political persona she’s carefully crafted.
The contrast is so stark, people are speculating whether this makeover is about more than personal growth. Some believe it’s tied to her new marriage to real estate developer Nicholas Riccio, who is 33 years older. Married for less than a year, the couple’s age gap has fueled suspicions that Leavitt’s fashion evolution is more about adapting to a social circle than professional demands.
Her current wardrobe leans hard into matronly silhouettes, oversized dresses, and head-to-toe black — choices that many say visibly age her. One two-photo collage shared online, showing Leavitt in 2021 versus 2025, drew thousands of reactions.
Karoline Leavitt HATES these side-by-side photos.
— DonkConnects ♻️™ (@donkoclock) June 25, 2025
DO NOT REPOST, @PressSec does not want people seeing this. pic.twitter.com/MMC0o4w3oW
Still, she has supporters. Some see her style as fitting for her role.
“Her dress is perfectly respectable for the white house! Leave her alone,” one user insisted. And not everyone is throwing shade.
But it’s not just the tweed that’s keeping Leavitt in the spotlight.
A recent post from June 28 shows her posing in the Oval Office wearing a sleek black dress and matching pumps, her back turned as she glanced over her shoulder. The caption read: “Have a great weekend, everyone!” While some praised the look, others took it in a different direction, drawing a shocking comparison to Monica Lewinsky.
Whether praised or picked apart, Karoline Leavitt is being watched closely — not just for what she says behind the podium, but for every stitch of fabric she wears. She may be the face of Trump’s communications machine, but in the court of public opinion, she’s also become a case study about how young women in power are often judged by their looks just as much as their words.
