Kayleigh McEnany Outfits That Completely Missed The Mark

Before Karoline Leavitt, there was Kayleigh McEnany — the fourth of Donald Trump’s press secretaries during his first term, following in the footsteps of Stephanie Grisham, Sarah Huckabee Sanders, and Sean Spicer. McEnany stuck it out longer than the latter’s six months, serving from April 2020 until January 2021. While in the role, she often raised eyebrows for her questionable outfits, which some believed inappropriate for a high-level governmental position. It wasn’t just her clothing that sparked debate among fashionistas. Some of McEnany’s dodgy hairdos managed to beat Kimberly Guilfoyle’s, which, let’s face it, is quite an achievement. Not to mention McEnany’s eyeliner overloads that left even JD Vance in the shade.

She also came under fire for her combative attitude, insistence on parroting Trump’s narrative no matter how problematic, and her facticity struggles — preferring “alternative facts” like her predecessors. Ironic given that McEnany swore to tell the truth, the whole truth, and nothing but the truth during her first press briefing in May 2020. “I will never lie to you,” she vowed. “You have my word on that.”

While McEnany didn’t always stick to her word, she did stick by Trump, but her ceaseless loyalty bore no value either as she landed on Trump’s hitlist in May 2023, resulting in him nicknaming her “Milktoast.” Well, she may be gone from the inner sanctum, but McEnany’s many makeup fails and dubious dress sense mean she will never be forgotten.

McEnany’s biker chick casual Friday on a Tuesday

Kayleigh McEnany was dressed to the twos rather than the nines in April 2020 in a pair of skin-tight ankle-grazing black jeans, black stilettos, and an asymmetrical zip jacket that screamed biker chick. McEnany’s outfit was perfect for casual Friday — which the White House doesn’t have —but regardless, the day in question, April 21, 2020, was actually a Tuesday.

McEnany was photographed in this ensemble with the suited and booted Deputy Press Secretary Hogan Gidley and the new Director of Strategic Communications, Alyssa Farah Griffin, who was clad in a smart, knee-length, sapphire-colored pleated flare dress, light tan pumps, and a knotted paisley print silk scarf. The three gathered to watch Matt Gaetz brief reporters outside the White House’s West Wing on Trump’s pledge to financially assist small businesses and struggling hospitals during the COVID-19 pandemic. The serious nature of the day and the formal attire of the other White House employees made McEnany stand out more.

McEnany’s attire was all the more surprising given Trump’s now famous alleged decree that his female employees “dress like women.” Politico’s chief White House correspondent, Mike Allen, wrote about Trump’s outfit inclinations in his newsletter Axios in 2017. People were left scratching their heads over what dressing like a woman meant in the 21st century. And, although Allen said nobody’s quite sure, he shared that he’d heard Trump’s female employees, especially those who worked on the frontlines of his campaign, believed it was beneficial to wear dresses and skirts if they wanted to get into The Donald’s good books.

McEnany’s ill-fitting Barbie-girl getup

Gaining entry into Donald Trump’s holier-than-holy club apparently involves ditching mirrors and abandoning all self-awareness. Otherwise, it’s hard to explain the metamorphosis that newly appointed members all seem to go through. RFK Jr. has taken his MAGA transformation to the next level with a fake tan even worse than Trump’s, and Matt Gaetz’s purported Botox overload left him looking like a real-life “Beavis and Butt-head” combo.

Then, of course, there are the women. Mar-a-Lago face is clearly a real phenomenon, judging by Trump’s female devotees’ almost identical aesthetic transmutations and clothing evolutions. Even the oftentimes somber and frumpy Sarah Huckabee Sanders embraced the Barbiecore trend sweeping Trump-land (with dire results, unfortunately). But Kayleigh McEnany is certainly no Sanders, and she dived into her MAGA makeover like The Donald tackling a KFC bargain bucket.

Commenters on X noted McEnany’s ill-fitting ensemble when she posed for pics with Trump outside of St. John’s Episcopal Church, which was damaged during a protest. The curled and coiffed hair, the make-up, the too-tight navy jacket covered in buttons, the good old skin-tight ankle-grazing black jeans that she’d dusted off and stepped into again, the high-heel light tan pumps … it all, well … missed the mark, not to mention the fact it was totally inappropriate for such a sobering and impactful occasion. “Kayleigh McEnany looks like she accidentally put on an outfit from the closet in a Barbie Dreamhouse,” a detractor opined.

McEnany’s Mrs. Doubtfire floral horror

Kayleigh McEnany embraced her inner Mrs. Doubtfire in July 2020 with a floral frock that was as far from her usual monochrome ensembles as possible. The outfit would have been marvelous for a summer BBQ, ladies’ brunch, or a posh tea party. Still, the cheery and brightly patterned dress appeared totally inappropriate for a somber press briefing on an alleged Taliban Russian-funded plot to kill U.S. troops in Afghanistan.

McEnany’s inappropriate outfits and questionable style are the subject of great discussion among members of the social media fashion police. “How would you describe Kayleigh McEnany’s fashion style?” an X inquisitor asked in January 2021. They were flooded with decidedly negative opinions. But then, as Shakespeare’s tragic hero, Hamlet, decreed back in the day, “I must be cruel only to be kind.”

And cruel they were indeed. “Left over Simplicity pattern found in the bottom drawer of Sarah Huckabee Sanders’ desk,” one user quipped about McEnany’s style. “skin-tight & bright with a crucifix on top,” another wrote. Harsh as these assessments may be, they do seem to sum up McEnany’s floral look quite well.

McEnany’s skater girl dress

Kayleigh McEnany looked ready to hit the rink in September 2020 as she took to the Brady Press Briefing Room podium in the White House for a daily media update. Her dark navy skater dress, trimmed with brightly colored bands, comprised a hemline that was daringly (for McEnany) above the knee. The outfit flashed her tanned shoulders and legs.

McEnany may have appeared like she was up for some flirty fun, but not surprisingly, she was anything but. It was straight down to business for the press secretary, with the suitable level of gravitas that inevitably accompanied her bitter battles with the media, which made the little navy mini-skater dress appear all the more inappropriate. However, it quickly became apparent that she was, in fact, dressed entirely suitably as she proceeded to skate around answering any of the reporters’ questions directly, choosing instead to deflect attention away from Donald Trump and onto the Democrats.

In November 2020, Vanity Fair compared McEnany’s questionable bright and breezy style to that of a “car show spokesmodel,” and fully fitting with Trump’s obsession with aesthetics, especially regarding members of the opposite sex. The magazine talked to some of McEnany’s former classmates from Harvard who described her as a real-life “alt-right” Elle Woods from “Legally Blonde.” A character who’s also renowned for her love of pink and bright colors and penchant for inappropriate outfits.

McEnany’s sparkly Liberace look

Kayleigh McEnany was all sparkles in December 2024 with a jacket fit for the late, great Liberace himself, matched with skintight black leather pants. However, there wasn’t a bedazzled Rolls Royce or crystal-embellished grand piano in sight. Instead, there was a selection of veterans, first responders, and Fox News hosts milling around the Tilles Center for The Performing Arts in Greenvale, New York, for the Fox Nation Patriot Awards.

Unfortunately for McEnany, Fox Nation didn’t have a greatest press secretary category. Still, she clearly didn’t let that ruin her big night out. “I had a wonderful evening celebrating American heroes at the Fox Nation Patriot Awards!” McEnany posted on Facebook. Her former boss did score big league, though, or is it bigly? The debate rages on. Either way, Donald Trump was named the biggest patriot of the year.

He was clad in his usual ill-fitted blue boxy suit when he humbly took to the stage to accept the accolade. Compared to Trump’s everyday attire, McEnany’s sparkle overload looked even more inappropriate, better suited to a Met Gala red carpet than a Fox Nation awards show. And the jacket also came with a price tag that was more fitting for the former. The “Alyssa Pearl — Trim Sequin Jacket,” designed by Veronica Beard in collaboration with Poppy Delevigne as part of their “The Party Collection,” came with a hefty price tag of $998.