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‘27 Pushing 68?’—Karoline Leavitt’s Dramatic Style Evolution Has the Internet Seriously Confused

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Published On: July 6, 2025
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Since joining the Trump administration as the youngest-ever White House Press Secretary, Karoline Leavitt went through a massive wardrobe evolution. Many people comment that she has a bad way of dressing, older than her age. However, the grandma style wasn’t how she always made her fashion choices.

Christopher Cuozzo, who now dresses Leavitt, commented, “She leaves it to me.” In an interview with WWD, her stylist added, “She’ll look to me for colors and ideas. I’ll send her that and some products that have been modeled by my clients for inspiration. She will say, ‘Yes. No.’ but she leaves the design to me — lapels, buttons and linings.”

To understand her wardrobe evolution, we must take a look at her past photos. Although these days, occasionally, the 27-year-old White House Press Secretary dons attired tailored for her fit and age, she once made some heavy-risque choices.

One of her most memorable outfits has to be a white mini-dress, which she shared on her Instagram. The outfit was short enough to showcase her killer legs. However, it’s hard to imagine that Leavitt would be wearing this risque outfit during her current MAGA phase.

Notably, this outfit didn’t just showcase her far her fashion has fallen, but it also looked more like her. From a youthful look like this to her current wardrobe, it’s a transformation of her from an outspoken woman to someone advocating for Donald Trump.

 

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

 

A post shared by KAROLINE LEAVITT (@karolineleavitt) 

Her current fashion choice leans more into matronly silhouettes, head-to-toe black, and oversized dresses, which many would describe as a way of visibly aging her. While it might just be a MAGA effect, many doubt that her sudden wardrobe transformation has something to do with her marriage to real estate tycoon Nichols Riccio, who is 33 years older than her.

This photo from 2023 further showcases how far her personal style has changed. In this Instagram post, Leavitt, who was 25 years old then, posed in a bright green tank top, white jeans, sandals, and a small cork purse. She also flaunted a full Miami look in blonde straight hair and sun-kissed skin. While this beachside, laid-back look is far from her current matured, polished, and monochromatic style, it surely suits her better.

 

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

 

A post shared by KAROLINE LEAVITT (@karolineleavitt) 

The conversation about her wardrobe choice once again resurfaced after Karoline Leavitt posted a picture of her at the White House in a hot pink tweed dress and matching shoes. Some people commented that the outfit visibly aged her, “27 pushing 68,” one user commented.

Another took a jab at her almost 60-year-old husband: “Ahh, look another grandma outfit for her old man!” A third chimed in, “Go take care of your Grandpa…sorry I meant your sugar daddy.” Another mocked, “My mom is 80 and has that dress Karoline.”

Despite the criticism, many MAGA supporters continue to back her fashion choices, commenting that she dresses appropriately for her position. “Her dress is perfectly respectable for the white house! Leave her alone,” one individual defended her.

 

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

 

A post shared by KAROLINE LEAVITT (@karolineleavitt) 

While the biggest reason behind her dramatic wardrobe shift can not be unveiled, it once again starts the dialogue about how young women are often judged based on their looks. Perhaps, for someone in Leavitt’s position, the fashion choice evolution is inevitable, regardless of whether she wants it or not.

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Moupriya

An entertainment junkie and a big cinephile. She has a passion for cultivating compelling and impactful stories for her readers. As an avid pop-culture enthusiast for years, she is obsessed with writing about celebrities, royals, and the A-listers of Hollywood.

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