Tacky Outfits We Can't Believe Karoline Leavitt Actually Wore

During her time in the White House, Karoline Leavitt has not exactly established herself as a style icon. As the youngest White House press secretary in history, one might assume she's got a sense for trendy looks, but she's made no shortage of fashion mistakes in the brief time she's been serving as Donald Trump's mouthpiece. Leavitt has run the gamut of fashion faux pas, from rocking outdated quasi-vintage outfits that look more like old school uniforms to donning bright red bombshell dresses at the most inappropriate times.

The world has seen just how different Leavitt looked in some college throwback photos, and it seems her MAGA makeover may have somewhat ruined her sense of style. However, looking back through her social media posts and Instagram 'fit checks, it appears that Leavitt has always had a taste for the tacky and garish. From pink wrap skirts to skin-tight leather pants to a shimmering rose gold ski suit, here's a look at some of Leavitt's tackiest outfits we still can't believe she wore out of the house.

To celebrate her 20th birthday back in August 2017, Karoline Leavitt hit the town with her parents and her two older brothers, Mike Leavitt and Joe Leavitt. The future White House press secretary commemorated the special day with a snapshot she posted to Instagram and revealed a particularly tacky look that included a white halter top, long necklaces, and a hot pink chiffon wrap skirt that she paired with ornate sandals. While she captioned the pic, "Unconditional love for my people," it's hard to feel the same love for her clunky ensemble.

Karoline Leavitt flew out to Europe in February 2018, and spent some time in Florence, Italy, where she shared a look at her Italian vacation 'fit to Instagram. The baffling getup included a fluffy fur coat over a red knit turtleneck sweater, as well as checked black and white pants with a bright red strip down the side. She capped the chaotic ensemble off with chunky black and white boots and oversized glasses. The only thing as tacky as her wardrobe choice was her confusing caption: "Sun don't shine in the shade."

After her jaunt through Italy in February 2018, Karoline Leavitt headed to London, England, to go sightseeing with a friend. Leavitt opted to rock yet another tacky combination of looks in a photo she shared to Instagram, donning a black sweater and black leggings under a white coat. She then added a pink and gray tartan skirt cinched with a loose-fitting belt. The knotted belt and coarse texture made the skirt look more like a potato sack that had been hastily reassembled into a piece of questionable couture. It certainly didn't fit the regal vibe radiating from the iconic Buckingham Palace that loomed in the background of the snapshot.

It's no secret that Karoline Leavitt has worn her fair share of gaudy, overpriced floral dresses. However, she really outdid herself with this garish frock that she wore for Thanksgiving Dinner in 2020. The dress, which she showed off on Instagram, was a kaleidoscopic blend of purples, pinks, blues, and oranges that was somehow busy and boring at the same time. The long sleeves and awkwardly pleated ruffles just added to the surreal nature of the design, and pairing it with black boots didn't do a lot to bring any more class to the ensemble.

Nothing says "class" like decking yourself out in head-to-toe faux-gold. Karoline Leavitt showed off her sparkling, obtrusive metallic rose gold ski suit on Instagram while hitting the slopes at the Sugarbush Resort in Warren, Vermont, on December 31, 2021. Leavitt decided to ring in the new year in the snow, and made sure to rock a look that simply shimmered with flashy faux-elegance. However, the outfit could also be used to reflect sunlight and signal to search and rescue helicopters if she got lost in the wilderness, so maybe she's on to something.

There have been several times in the past when Karoline Leavitt was slammed by critics and commentators after rocking ridiculously oversized outfits that give off big-time preschool dress-up vibes. However, she went the opposite direction when she took her godson to a Boston Celtics game in April 2022. Leavitt instead opted for some skin-tight leather pants (always a tough look to pull off) and a jersey top, as seen in a photo she posted to Instagram commemorating the fun night out. What makes her awkward look even more head-scratching is her choice of wearing a Red Sox jersey to a basketball game — not to mention her decidedly non-sporty pair of tan heels.

In November 2022, after losing her US congressional campaign in New Hampshire, Karoline Leavitt decided to decompress and relax. She took to Instagram to share some snapshots of her vacay outfit, and once again proved that she doesn't quite know the difference between chic and cheap. Leavitt flaunted the curve-hugging neon blue minidress with a big smile, despite the fact that the semi-sheer dress' abstract design and color scheme made it look like it was melting down over her figure. More than two years later, one commenter returned to the post and succinctly criticized the look, calling Leavitt the "Secretary of Shoes that are Too Small."