Karoline Leavitt's Spiciest Outfits Clash With Her Press Secretary Persona

Karoline Leavitt may have outspoken opinions, but the White House press secretary's wardrobe choices don't always match her out-there remarks. The controversial star clearly has an interest in fashion, as she's been spotted in pieces from plenty of big name designers. Just some of the luxury pieces in her lookbook? Items from Gucci, Luis Vuitton, and Jimmy Choo. 

But despite having access to the most expensive fashion houses in the world, Leavitt has still worn a handful of outfits that missed the mark and is often seen at work in some very frumpy, downright boring looks that age her beyond her years. She mainly sticks to safer, professional, and modest garments during her many press briefings. But don't be fooled into thinking Leavitt — who was born in 1997 — doesn't have a few spicier looks in her closet. On numerous occasions, Trump's go-to media woman has sported some outfits that straight up clash with her buttoned-up press secretary persona.

When Karoline Leavitt attended the Conservative Political Action Conference (CPAC) in 2024, her outfit did everything but make her fade into the background. The future press secretary wore a sleeveless leopard-print midi dress with black, stiletto, pointed-toe, tall, leather-look boots. The bold and feisty combo marked a stark contrast to her usual pantsuits and corporate dresses, and we appreciated Leavitt stepping out of her often-frumpy workwear comfort zone to try a daring print. Though the shoe choice may have been wrong for Leavitt's animal-print dress, we still liked that she thought outside the box and tried something less bland.

At work, Karoline Leavitt's style is sophisticated but understated, which is why we were surprised to see her don a rose gold snowsuit during a 2021 Vermont vacation. Leavitt stood out in the vibrant, out-there number, which featured head-to-toe shine and a flattering waist-cinching belt. "Now that's a ski outfit," one person commented on her Instagram upload, as she paired the bold all-in-one with pink and orange, two-tone ski goggles. The look gave us Mariah Carey diva vibes (in a good way) and the whimsical garment showed her fun and daring style side, which we don't see very often.

Karoline Leavitt looked stunning in a 2020 Instagram upload posing with Barstool Sports' Dave Portnoy. Her form-fitting LBD was one we could imagine on little black dress queen Reese Witherspoon, as it gave us lingerie vibes thanks to it's nude-lined, lace bodice. Even though Leavitt wasn't showing an excess of skin, the sheer-illusion top was undoubtedly very different from her starchy work looks. The spicy knee-length number flattered her frame thanks to its form-fitting material and was gorgeous against her tan skin. Leavitt's worst outfits may all have one thing in common, but it's not being little black dresses.

Karoline Leavitt showed her flirty side in a summer 2019 Instagram upload that saw her in a satin white mini dress with criss-cross straps that revealed her bare back. The avid President Donald Trump supporter wore her long, straight hair in a slicked down ponytail with ribbon tied around her locks, which added to her chic yet breezy aesthetic. The silky material marked a fun change from Leavitt's usual go-to looks made of thicker fabrics and conservative necklines, while the shorter length made her aesthetic more fun and youthful.

For the holidays in 2020, Karoline Leavitt slipped into a fiery red, all-sequin dress that left her followers dazzled. Though we don't see the divisive star wearing full-on sparkles very often, this look proved she can more than pull them off. The plunging maxi dress was far more glamorous and exciting than the numbers we're used to seeing her in at The White House and was well-tailored to fit her figure. "ZAYYUMMM," one fan commented on the upload alongside a fire emoji, as this dress certainly made a statement.

Abiding by trends may not be easy for Karoline Leavitt, who has to ensure she's dressed appropriately for political work, but she was clearly paying attention to what the world was wearing in 2023. She sported an all-black, athleisure number on Instagram, including a plunging top with form-fitting shorts and white sneakers. The New Hampshire native's modern and minimalist ensemble felt a world away from her corporate looks and spiced things up by highlighting her figure and showing a little skin. The casual, laid back look wasn't something we'd expect to see a one-day White House secretary in, which makes it all the more striking.