Karoline Leavitt's Sexiest Outfits Before Becoming Press Secretary

Karoline Leavitt has undergone a stunning transformation since becoming the youngest White House press secretary in history. Her style also did a complete 180, going from fun and flirty to full-on grandma within the span of just a few months. During her first media briefing in January 2025, Leavitt sported a purple suit with a black top and her signature cross necklace that seemed to age her by a few years. Since then, she has stepped out in a string of frumpy outfits that prove her style game is slipping hard.

There was one time she confused the White House for an '80s pajama party and another when she tried to bridge the age gap with her husband in her stuffy old lady outfit. (She and Nicholas Riccio share a whopping 32-year age gap.) However, Leavitt, who's only 27, didn't always dress so conservatively. In fact, she used to turn heads with her daring outfits that captured her youthful spirit. Join us as we take a look at Leavitt's sexiest looks before her style took a nosedive.

Before joining the White House, Karoline Leavitt wasn't shy about showing off her figure — whether through a figure-hugging dress or a busty outfit. In September 2023, she shared an Instagram snapshot from Labor Day Weekend in Napa Valley, sporting a halter-style cropped top that offered a rare glimpse of her décolletage. The top had a matching skirt, which Leavitt styled with heeled sandals and a shoulder bag with gold straps. Her waist was also exposed, and she wore her hair styled in a bun while holding a glass of champagne. Chic? Perhaps not exactly, but it's nice to see Leavitt in anything other than her usual old lady jacket and frumpy trousers.

Seen here posing on a balcony with an amazing view of the city, Karoline Leavitt flaunted her curves in a sleek, body-hugging dress with a halter neckline. In the snap, she stood sideways with her left leg slightly in front of her right, striking a pose that highlighted her backside. She completed her look with a small woven bag and block heels with clear straps. The image was part of a photo carousel thart Donald Trump's press secretary posted to Instagram in June 2023 to recap her month. As expected, the comments were full of fans thirsting over her look, with one fan gushing, "Body of all bods," while another exclaimed, "Stunning, beautiful! MAGA women are so hot!"

One of Karoline Leavitt's busty outfits we doubt she'd ever wear today was her game-day look for the Boston Celtics vs. Miami Heat matchup in Florida. Showing her support for the Celtics, Leavitt donned a bright green top with thin straps and a low scoop neckline that showcased both her arms and cleavage. She paired them with white jeans before finishing the look with a small handbag and the same block heels from earlier. She quoted NBA star LeBron James in the caption of her post, writing, "'I'm taking my talents to South Beach.' Go Celtics!" Once again, fans flooded the comments with praise, with one gushing, "Green is her color," while another user added, "This outfit would be the only reason I'd go to a sporting event."

Karoline Leavitt had a knack for wearing risqué outfits prior to making history as the youngest-ever White House press secretary. At the 2020 White House holiday party, Leavitt — then an assistant press secretary — wowed in a glittering red dress with a deep plunging neckline. The dress highlighted her frame and gave her followers an eyeful of her assets. In the pic, she posed with her then-boyfriend, who wore a look straight out of Donald Trump's playbook featuring a navy blue suit and a classic red tie. "Hottest lady in the world," one fan gushed, while another exclaimed, "You guys look amazing." A third user added: "Stunning, Ka!"