Karoline Leavitt’s fashion fails: 7 times WH press secretary raised eyebrows with her outfit choices

WASHINGTON, DC: White House press secretary Karoline Leavitt may be just 27, but her wardrobe choices often tell a different story — one that’s drawn more criticism than compliments.

Leavitt’s oddly mature and frumpy fashion sense has sparked everything from eye-rolls to political debate, with some calling for her to trade the “granny garb” for something more fitting.

Whether she’s trolling critics or trying to connect with Gen Z, her controversial looks have stirred reactions across social media, as per Nicki Swift. Here are seven instances where Leavitt’s outfit choices missed the mark.

1. Leopard-print 2025 CPAC outfit

One of the most recent criticisms of Karoline Leavitt’s fashion choices came after she attended the 2025 Conservative Political Action Conference (CPAC).

For the event, she opted for a bold leopard-print ensemble paired with knee-high black boots — a look many felt was more fitting for a night out than a professional political gathering. The outfit sparked fresh debate about her sense of occasion and judgment in public appearances.

2. Crystal-embellished Self-Portrait minidress

Over time, some critics have pointed out that some of her clothing choices miss the mark in terms of appropriateness for formal or political settings.

One of the pieces in Leavitt's wardrobe that has raised eyebrows is a crystal-embellished mint green minidress from Self-Portrait. She wore it during a South Lawn event and a press briefing in March.

The dress featured a prim, grandmother-style top paired with a more glamorous, party-ready skirt. Notably, the same outfit was worn by Paris Hilton in a more fitting context—while filming her reality series 'Paris & Nicole: The Encore'. 

3. Presidential debate plaid miniskirt-blazer combo compared to an outfit from ‘Clueless’

In 2024, Karoline Leavitt chose to wear a plaid miniskirt and blazer to a presidential debate, a look that many compared to an outfit from the movie ‘Clueless’.

The choice was widely criticized for being inappropriate for the serious nature of the event. Given her boss's stance on immigration, it seemed even more out of place, as Leavitt would likely dismiss the iconic line from the film, "It does not say 'RSVP' on the Statue of Liberty." 

4. 'Republicans are hotter' hat 

In 2023, Karoline Leavitt shared a casual photo of herself dressed in a black tank top, Daisy Dukes, and a snapback hat, emblazoned with the phrase "Republicans are hotter," promoting the conservative dating app, Date Right Stuff.  

At the time, she was a failed congressional candidate who had adopted the tactics of criticizing Democrats, much like her former mentor, White House press secretary Kayleigh McEnany.

Rather than using the opportunity to defend her party’s policies or highlight Trump's achievements, Leavitt’s intention seemed more focused on making a superficial, attention-grabbing statement.

5. Flashy zebra-print dress 

For an event at Mar-a-Lago in 2023, Karoline Leavitt wore a bold green zebra-print dress, which quickly drew criticism for being too flashy and inappropriate for a professional setting.

The dress, which resembled the bright, garish hues of Fruit Stripe gum — famous for losing its flavor almost immediately — looked especially out of place amid the extravagant gold decor of Trump’s beach club. 

Despite the outfit’s questionable style, Leavitt believed it was suitable for work, captioning a photo of herself in the dress with, "Here for business and pleasure."

6. Inappropriate White House Christmas party ensemble

In 2020, Karoline Leavitt drew criticism after choosing to wear a glittery red dress to the White House Christmas party.

While the ensemble was undeniably festive and eye-catching, many felt it leaned too heavily on glamour and failed to reflect the more serious tone the occasion called for, particularly during the height of the global pandemic.

The event also offered her a chance to emphasize her Christian values, but some observers noted the absence of her usual cross necklace, which might have clashed with the bold, revealing neckline of her dress.

7. Heavily distressed jeans from a soccer match in 2018

In 2018, Karoline Leavitt attended a soccer match wearing a T-shirt that showed her support for Italy’s AS Roma football club. The choice of top was casual and appropriate for the event. However, her jeans sparked some criticism.

The heavily distressed denim featured a large rip high on the thigh, which many felt was too revealing for the occasion. The outfit gave the impression that she was more interested in drawing attention than dressing suitably for a sporting event.