Karoline Leavitt's Most Outdated Looks That Had Us Checking The Calendar

Karoline Leavitt's known for her penchant for experimenting with fashion. Unfortunately, her choices often lack finesse, resulting in outfits that completely miss the mark. Although the Gen Z-er is the youngest White House Press Secretary ever instead of taking the opportunity to display a youthful vibe, Leavitt frequently opts to dress way older. In addition to being unflattering, her ensembles often channel trends that are better left in the past.

One of Leavitt's preferred styles is her selection of bouclé dresses. These frequently showcase prominent shoulders and square chest pockets. While bouclé is featured in current styles, Leavitt's attire looks entrenched in the 1950s, the fabric's original heyday. Her dresses often include excess embellishments on the pockets, collar, and down the front of the dresses, making them look old-fashioned. Unfortunately, Leavitt's outfits are often wildly expensive. According to the Irish Star, one of these blinged-out, retro-looking dresses costs $555. For that price, an authentic vintage outfit would be much cooler.

Even when she chooses options that aren't as heavily decorated, Leavitt's pastel colored wardrobe also gives her look a very mid-20th century aesthetic. For instance, Leavitt wore a baby blue dress with a pleated skirt and topped it with a matching cardigan with gold buttons. The whole ensemble was reminiscent of '50s-era sweater sets and too matchy-matchy. This isn't the only era where Leavitt's stuck in the past. Her outdated choices are all over the decades, including '90s fake-looking leather and an '80s style suit. Let's take a look.

When Karoline Leavitt wore a leopard print dress to CPAC in February 2025, it felt like a callback to the dawn of the 21st century. Although leopard is a timeless choice, it's not impervious to looking outdated. In this case, her dress's hem looked like it was an odd length –- too short to reach her ankles, but too long for midi length. Leavitt paired her dress with high black boots, adding to the sense of hem displacement. Since the dress dominated Leavitt's look completely, it felt more akin to Mel B's signature Spice Girl-era leopard print jumpsuit, rather than an updated take on an enduring print.

Unfortunately, that same day, Leavitt accessorized with a bulky, fuzzy-collared coat. While it toned down the loudness of the leopard print, the bland beige wasn't the best choice color-wise. Had she worn a black coat, it would have made the leopard spots pop, elevating the look.

Leavitt's had tough luck with animal prints before, like when she wore a polarizing green zebra print dress in March 2023. One Instagram commenter had an interesting observation, writing, "That dress almost looks flavored." While some would contend that zebra print is a modern choice, the unusual color might be its biggest stumbling block. One YouTuber recommended sticking with animal prints in their natural hues. "It does not need a splash of color," she contends. "It makes it look comical, cheap, and not sophisticated."

In May 2023, Karoline Leavitt paired a pink suit with a silky bow-tie blouse. Sometimes referred to as a pussy bow, this type of blouse became particularly popular beginning in the mid-20th century. Lately, it's been a go-to choice among politicians. Even so, this is a resurgence of the trend, since Margaret Thatcher also wore pussy bows when she was Britain's prime minister in the 1980s.

Leavitt appears to be channeling Thatcher's iteration, and her outfit looks like it came straight out of that same decade. Initially, the pink shade could be construed as modern, since 2023 was peak Barbie-core. However, Leavitt's had many unsuccessful Barbie-core looks, and this pink suit can be added to that list. If Leavitt took a time-machine to the mid-1980s, she'd fit right in. "That was during the whole reign of the floppy bow tie and the suit," a fashion journalist explained to NPR. "That was the look most women wore in their 20s and 30s when they started in the workplace."

Wherever she is in time, Leavitt might want to seek out a tailor. The sleeves of Levitt's suit jacket are too long, and she has hastily cuffed them, resulting in a sloppy look. While cuffing can be chic in some instances, Leavitt might be better off cuffing the sleeves a couple times and pushing them up to make the look appear intentional, rather than as a quick fix for a poor fit.

With their clean lines, sheath dresses are an enduring style. Unfortunately for Karoline Leavitt, it's her choice of material that makes one of her black dresses look firmly rooted in the past. In October 2024, Leavitt attended Donald Trump's Madison Square Garden rally wearing a dress with a textured pattern. The unwavering evenness and shininess of this pattern makes the dress appear to look like '90's era pleather aka "plastic leather." Besides the cheap appearance of the material, some social media users felt it was more suited to going out to a club rather than wearing to a political event.

Genuine leather vs faux leather can be a fraught decision. Leavitt herself alluded to concerns about wearing animal-derived clothing in a February 2023 Instagram post. She wore a black leather vest with a furry collar, and her friend wore a fur coat. "The fur is fake. @peta don't come at us!" Leavitt remarked. Unfortunately for Leavitt, the overly shiny vest looked unflatteringly fake.    

While these pleather items might be better off for a '90s-themed party, Leavitt has had success with leather, like when she wore a pair of leather pants with a double-breasted blazer. Even though it's impossible to tell the material without consulting the tag, these pants have a satiny-smooth look that appears to be quality leather. Luckily for Leavitt, numerous vegan leather options exist, giving her plenty of choices so she can avoid outdated plastic-looking outfits.   

Karoline Leavitt's been accused of grandmacore gone wrong, and she made that mistake in November 2024 by pairing very high-waisted black pants with an overly-embellished scalloped-hem cardigan. Between the super-'70s era waist line, and the '60s-eque beaded cardi, Leavitt's mid-century mashup isn't winning any fashion accolades. 

Not only does the clothing itself make her look far older than her 27 years, the outfit could benefit from some styling tweaks. For example, instead of tucking in her pale pink top and revealing lots of wrinkles at the waist, Leavitt may be better off pairing these pants with a longer shirt or jacket to lengthen her torso. 

"Bad outfits can happen to good pieces," explains "The French Chic Expert" YouTuber Marie-Anne Lecoeur. "Don't think it's because of each piece, but rather it is those pieces together that don't work." Lecoeur even has a fuzzy, beaded cardigan that looks like it came out of Leavitt's closet. She combines it with white pants to match the cardigan, and then adds a black, collared shirt for a stylish defined neckline that complements the cardigan's design. As a finishing touch, Lecoeur accessorizes with a black belt, accenting her waist. Similarly, Leavitt could follow this strategy and bring her love of beaded designs in the modern world. She could swap the pink tee for a button-down shirt. A  belt could also be helpful, and make Leavitt's pants look less athleisure and more polished.