Inappropriate Press Secretary Looks That Did Not Belong In The Briefing Room

The mouthpiece for the President of the United States is none other than the White House press secretary. Press secretaries handle communications from the president to the public and are constantly at the forefront of media coverage from the White House. Of course, that means that not only will the general public pay incredibly close attention to every single thing press secretaries say, they will also keep an eye on seemingly frivolous things — such as hair and fashion choices made for press briefings.

The press secretary for Donald Trump's second term, Karoline Leavitt, has been criticized for dressing older than she is and rocking the wardrobe of a "Golden Girls" extra (not to mention, her Trump-like lack of a filter has raised eyebrows). However, some of her professional looks have been on the opposite end of the spectrum, looking less appropriate for official business and better for a night at the El Presidente restaurant in Washington, D.C., for a Wolf Spritzer. And Leavitt definitely isn't the only press secretary to fall into that trap.

In May 2025, Press Secretary Karoline Leavitt wore a black outfit for a press briefing. In an attempt at professionalism, there was a set of buttons up the front and a collared neckline. However, the one missing factor was sleeves.

Maybe if this was an outdoor event, like the Easter Egg Roll, this look (and Leavitt's corresponding claw clip with white flowers) would've been picture-perfect. However, for a run-of-the-mill, indoor press briefing, Leavitt looked woefully underdressed.

Since receiving the title of Governor of Arkansas, Sarah Huckabee Sanders' style has included ill-received leather looks. However, during her tenure as press secretary, she was more often seen in shift dresses. For instance, while speaking to reporters in May 2019, Sanders wore a cobalt blue, knee-length frock.

With its fun color and fluttery sleeves, this dress looks like it would fit right in at a tea party, a luncheon, or similar social outing — and is absolutely not the right vibe for answering questions on election interference.

Fox News' Kayleigh McEnany has had fashion fails on the network. When she was Donald Trump's press secretary in 2020, her worst look photographed by the media wasn't a neon green blazer (unlike a different press secretary), but a shiny black pair of leather (or pleather) pants. The skintight trousers looked wrinkled as McEnany walked, and she paired them with a black top and a gray jacket that seemed to be channeling a totally different aesthetic.

These pants would be better suited for girls' night out, not 1600 Pennsylvania Ave. Surprisingly, that wasn't the only biker-like look of McEnany's that missed the mark.

Accessories can make or break an outfit, and Sarah Huckabee Sanders' bright red heels are an accessory she should have left on the shelf for a May 2019 press briefing. Her simple black dress and white pearl necklace were a nice, classy choice for the event, though her distracting red shoes clashed with the look.

Sanders should've opted for a simple pair of heels in a neutral color. Her shoes didn't need to be a conversation piece as she debriefed the state of the administration.

Karoline Leavitt has had rare success wearing green, and her neon suit jacket from June 2025 can be added to her list of green fashion fails. Paired with black slacks, the baggy blazer is slightly too big for her, with the sleeves rolled up so they don't cover her hands. It also possibly has padded shoulders, evoking power suits of the '80s.

In a more palatable color, the poor tailoring of the jacket might not be as noticeable. But Leavitt's choice to rock such a blazer in an eye-wateringly bright shade of green is what tips this look over the edge into inappropriate. This is giving costume party vibes, if Leavitt was going as the Grinch on a work retreat.