Trump’s Aides Aren’t Strangers To Wearing Some Inappropriate Outfits

Donald Trump has had plenty of different aides throughout his political career so far, and quite a few have caught the public’s eye thanks to their interesting (or sometimes just awful) fashion choices. The aides are often photographed together or with Trump at the White House or at various events having to do with the president.

The president’s aides are in the spotlight a lot, and because of that, they go through plenty of outfits. Whether it’s Natalie Harp and her killer legs, one of the many Melania Trump clones like Margo Martin, or prominent members of Trump’s team like Press Secretary Karoline Leavitt, they each need a very deep closet.

With all this in mind, it should likely be no surprise that these aides’ wardrobe rotations can be hit or miss. Some are even borderline inappropriate for the kind of political job they have. Looking back at some of the most daring outfits from Trump’s aides over the years, it’s clear that some of these ensembles were just a little too questionable for the job.

While Hope Hicks isn’t working for Donald Trump anymore, she spent a lot of time in the White House as his communications director, among other positions. During her time on the job, Hicks generally kept to a chic and monochromatic style, but she occasionally tried some more daring options, such as a few pairs of over-the-knee heeled boots. These are generally associated with sorority girls, not White House staff. As one person wrote on X, “Thigh-high boots is not an appropriate outfit for an [economic] summit! Best to keep that for a night out on the town.”

Margo Martin, a special assistant to Donald Trump and a communications advisor, looked a little too casual in her outfit while attending an economic event at the Coosa Steel Corporation with the president in February 2026. Martin, who was 30 at the time, wore a gray sweater, relaxed black pants, and white sneakers while she kneeled on the ground to get the right angle with her phone. She definitely looked out of place around people in suits and elegant outfits (and chairs). Considering Martin’s well-known lavish lifestyle, she can likely afford a more appropriate outfit for such events.

There have been times when Margo Martin may have forgotten she’s an aide to the president and not an aspiring runway model. Another inappropriate example of this came in August 2024 when she joined Donald Trump at a campaign rally in Pennsylvania. The audience was likely distracted by the aide’s risqué choice of outfit, a blue shirt-dress with white stripes — and that’s it. It looks like she simply threw on a partner’s button-up and called it a day. It’s just one of many outfits we can’t believe Martin wore. 

As the White House press secretary, there’s a lot of pressure on Karoline Leavitt to have an array of unique outfits for every appearance. That doesn’t mean every look is a winner, though. In June 2025, Leavitt wore black pants and a bright green jacket with shoulder pads straight out of an ’80s music video like “Once in a Lifetime” by Talking Heads. Given Leavitt’s smaller frame and more serious role, it was downright comical to see her walking around in it like a child in a trench coat.

Kayleigh McEnany served as Donald Trump’s press secretary between April 2020 and January 2021. During her tenure as one of Donald Trump’s aides, she attempted several party-girl outfits that would never cut it in a normal workplace environment. In September 2020, for instance, McEnany addressed the press in a bright turquoise dress that was nearly skin-tight. The color itself was a little jarring, but what made the outfit even more inappropriate were the cutouts at the front neckline. While some cutouts can be chic, they’re hardly ever professional.

Kayleigh McEnany seems to love bright colors, from painful pastels to nauseating neon. She could’ve blinded the media when she wore this overly colorful, patterned dress to a White House press conference in July 2020. McEnany looked ready to head out for brunch with her friends instead of fielding questions about important things, such as the global pandemic that was killing millions at the time. Along with the eye-catching print, the dress was made even more questionable by being worn off-the-shoulder. If anything, it was more “hoedown” than “lockdown.”