7 Outdated Press Secretary Outfits That Were More Retirement Home Than White House

When you're the White House press secretary, it's important to keep the media informed, advocate for your administration's agenda, and continuously butt heads with reporters, apparently (just look at the vitriolic feud between current Press Secretary Karoline Leavitt and CNN's Kaitlan Collins). However, as you are the face of the White House, so to speak, it's also a good idea to bring your A-game when it comes to your fashion choices and show off your style sense. It can be a difficult balance between over-dressing, as in rocking something a bit too glam for the situation, or going for the opposite end of the spectrum and wearing something that looks like you pulled it out of your great-grandmother's closet.

As one of the press secretaries who worked under Donald Trump during his first time in office, Kayleigh McEnany often struggled with this balance, donning leggy and inappropriate dresses to important briefings — or her ensembles completely missed the mark in different and confounding ways. On the other end of the spectrum is Leavitt, who has routinely dressed way older than she actually is. It's a daily challenge that has faced numerous women in that role in the past, and quite a few times we've seen some bizarrely outdated ensembles that really gave off an unfortunate retirement home vibe.

While adding a pop of color can always liven things up, Karoline Leavitt's decision to brief the press while rocking this pinkish-purple ensemble didn't exactly instill confidence when it comes to her fashion sense. The knit top, with its large, clunky silver buttons, feels like it was made out of the same kind of yarn-woven fabric everyone's grandma keeps on the guest bed, and it doesn't help that the slacks look like light purple sweatpants. All in all, no one would be surprised to find this sort of look in a moth-riddled closet, but it was surprising to see it on the White House's youngest press secretary.

While Karoline Leavitt might be too young to really remember the days of analog TV, it sure seems her shirt is based on the static you'd see when the signal went out in the old days. You can all but hear the crackling screech of TV static just by looking at this black-and-white, headache-inducing, short-sleeved blouse, making it feel like a relic of a bygone era. The similarly patterned, seemingly fabric buttons and vaguely frilly hem around the collar and cuffs don't do much but add an unfortunate retro vibe to the already outdated garb.

When Sarah Huckabee Sanders was the White House press secretary under Donald Trump during his first term, she woke up one day and decided to wear the most bland, shapeless, neon coral dress ever crafted by man. Despite the bright color, the pinkish orange look had an "Easter at your grandparents" vibe already before Sanders opted to pair it with a traditional, borderline antique pearl necklace. The piece looked like something directly out of Barbara Bush's jewelry drawer, save for the fact that it was more boring than the Bush matriarch's trademark triple-strand necklace.

Dana Perino, a White House press secretary under President George W. Bush, certainly didn't have an easy job in September 2008, when she had to answer questions about the administration's massive bailout bill. Perino likely went for a look that meant to suggest austerity, but the high, buttoned collar blouse looked like something you'd see on an old, retired warrior monk in one of the lower-budget "Star Wars" spin-off shows. If she was going for a look that was intentionally low-key with elements of sartorial restraint, she overshot the mark and landed on something that was paradoxically, fascinatingly boring.

Jen Psaki, who served as a White House press secretary under Joe Biden, was easily one of the most stylish and fashionable press secretaries of all time. However, even all-stars have off days, and that seemed to be the case when she wore this bizarrely bland and uncomfortable-looking number to a press briefing. From the plum material that looks like it was sourced from a thrift store couch; to the brassy, ornate buttons; to the frilly hem around the neckline that simply looks like the fabric has frayed, everything about it feels decades old. Its style fits in with the kinds of clothes the American Girl Historical Character dolls based around the early 20th century might wear.

Kayleigh McEnany served as the White House press secretary under Donald Trump during his first term — and from the look of this outfit, she also served as an admiral in some sort of imaginary, glam fashion Navy. First direct your attention to the dark jacket, with way too many white buttons next to the lapels that don't actually make any functional sense. Notice the equally inexplicable line of five buttons on her sleeve cuff as well. You will soon realize that she's seemingly wearing this jacket over a zip-up top, which comes complete with its own high-collar sticking out of the jacket, and it's lined with a tiny strip of fleece like an old-timey bomber jacket. Every bit of this feels like someone cosplaying as military commander to recapture some old glory, and it's utterly baffling.

The 1990s was a very different time for fashion, and certain looks that were trendy then would be outdated and questionable now (though some '90s trends have rebounded, for better or worse). Even for the '90s, Dee Dee Myers' decision to wear an amorphous pink and white, long-sleeved polka dot dress, paired with a pearl necklace no less, was a poor choice. Myers was the first-ever female White House press secretary and, at the time, one of the youngest ever. She was 31 years old when she rocked this colorful misfire in May 1993. While it's the kind of dress that would undoubtedly bring a pop of color to a bingo hall on a Saturday night, it still seems remarkably out of place for a White House press briefing.