For being the youngest White House Press Secretary in United States history, Karoline Leavitt presents herself as an old soul. The transformation of Leavitt from failed congressional candidate to manning media blitzes on behalf of President Donald Trump, she’s certainly gained access to an exclusive inner circle. Leavitt’s sense of fashion, however, feels anything but celebratory. There have been several times Leavitt’s outfit has missed the mark, leaving a trail of questions behind as to who styles her and why she has such a fondness for sweater sets. In fact, it’s Leavitt’s consistent inclination to dress in dowdy, old-timey clothes that makes her youth feel incongruent to her reality.

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There was the time Leavitt wore a pantsuit fit for a nursing home as well as her rather outdated Easter dress debacle that shows the press secretary is stuck in the past. But these are just two examples of Leavitt’s fondness for demure doily-inspired dresses. As she settles into her role — which requires her to be in front of the camera on a regular basis — it seems the message she’s trying to send with her outfits is one of grasping for authority by dressing like a school principal from the 1950s.

While it’s unclear if this strategy is working, what is clear is that there’s many more times Leavitt has worn clothes that have been more fit for a grandma than a new mom. Here’s five times Leavitt dressed significantly older than she really is.

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With Karoline Leavitt determined to firmly nest herself within the inner circles of President Donald Trump’s administration, it makes sense that she would surround herself with other true believers. In an Instagram post simply captioned “WOMEN FOR TRUMP,” Leavitt is surrounded by some of the MAGA elites. Once again, Leavitt finds herself to be the youngest of the bunch, with Sarah Huckabee Sanders, Tulsi Gabbard, Danica Patrick, Lara Trump, and Kristi Noem all at least a decade older than the press secretary. However, despite being the youngest in the bunch, Leavitt picked the dowdiest clothes to wear.

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While Leavitt and her rumored plastic surgery fit right in, standing next to Lara and Noem  — two women who also have surgery speculation following them — she still misses the mark. In her pastel pink top and morbid black cardigan, Leavitt looks ready for a bingo hall. In fact, Patrick has a more youthful glow than Leavitt does here, showing off her toned arms in a fun belted tank top look. Noem, being the oldest of the group, is also in an outfit that makes her appear younger than Leavitt. It’s proof that Leavitt’s closet full of grandma sweaters is not helping her fit in, even with women much older than she is. 

There are plenty of red flags within the marriage of Karoline Leavitt and Nicholas Riccio, one of which is the lore surrounding their wedding. Not only does the couple boast an impressive age gap, with Riccio being more than 30 years Leavitt’s senior, but for being such a conservative-leaning couple, they certainly did some things out of order. Leavitt and her husband had welcomed their son, Nicholas “Niko” Robert Riccio, before getting married. When the couple was finally ready to tie the knot, Leavitt certainly chose quite the questionable wedding dress.

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In an Instagram post to celebrate the occasion, Leavitt admits she “finally found some time to post a few of my favorite pictures from one of my favorite days!” Within the carousel of photos is her repeatedly posing in her dress — a silvery white garment that appears to be something a 1920s flapper would wear instead of a 2020s bride. In fact, according to David’s Bridal, this dress is inspired by the lavish parties thrown in “The Great Gatsby” — not the cutting edge of youthful fashion. The beading creates an art deco-inspired look, which is great for architecture but tricky for clothing. Considering that Leavitt’s husband is a millionaire, the low price tag of under $700 for the dress calls into question just how well thought-out the wedding truly was.

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Seen here arriving for a White House press briefing, Press Secretary Karoline Leavitt is in an outfit that has become a staple of hers: the matching sweater set. Historically, these boxy and slightly fuzzy cardigans are paired with a matching shirt underneath and a skirt or pair of pants. Brought to the height of popularity by previous first ladies Nancy Reagan and Laura Bush, the twinset harkens back to the era of World Wars and rationing. It’s an interesting choice for Leavitt to have in her closet.

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Notoriously, the post-war twinset era was the beginning of the women’s liberation movement as more women began working outside of the home. But Leavitt’s sweater set conjures up an image closer to pearl-clutching than self-idealization. With Donald Trump and wife Melania Trump’s outdated sense of fashion firmly set in the 1980s, it makes sense that Leavitt would want to play to these sensibilities. It could be that Leavitt is trying to fit a throwback-inspired mold, but she’s ultimately falling short. Even her youth cannot save Leavitt from dressing like a reanimated Molly McIntire American Girl Doll.

There’s classically chic, and then there’s Victorian-era modesty. Even though Karoline Leavitt started her job as press secretary in her 20s in 2025, she seems to be stuck dressing in styles closer to that of an elder from the 1870s. Channeling a look closer to “Little House on the Prairie,” Leavitt waltzed up to reporters in a dress fit for Laura Ingalls Wilder. Once again swimming in a boxy cardigan, Leavitt’s overall outfit is not just dated, but ill-fitting.

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The sleeves are much too long for the rather petite Leavitt, swallowing past her wrists and covering most of her hands. Her sweater also cuts her off at an awkward point of her waist, making the matching set feel incongruent. Plus, the hem of the skirt hits Leavitt just above the ankle, making her appear shorter and squatter than she really is. Had she swapped out the sweater for a blazer and her skirt hit just a bit higher on her leg, this would have been a classic look instead of a frumpy one.

On March 27, 2025, Karoline Leavitt wore her frumpiest outfit yet. Perhaps in an effort to distract from the leaked Signal group chat, Leavitt dressed up from an era where telephones didn’t exist at all. In an ill-fitting powder blue school teacher outfit fit for the 1800s, Leavitt proved that she’s firmly trying to make this fully buttoned-up style her signature thing. However, it leaves much to be desired.

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Again, due to her small stature, this belted dress causes her to appear doll-like and as if she doesn’t have money for a tailor. The sleeves are too long and bulky, the waist isn’t cinched in enough — making the belt appear to just be for show — and again, the cut of the skirt makes her look overly short. There are plenty of ways to modernize this look; had she rolled up her sleeves, tightened the belt, and unbuttoned the top two buttons, the whole fit would have brought a relaxed springtime vibe. Instead, Leavitt appears insistent on becoming the real-life embodiment of the character Angela from “The Office.”