7 Outdated Kayleigh McEnany Outfits That Should've Never Left Her Closet

Even with her storied career of serving in the White House and hosting several shows for Fox News, Kayleigh McEnany still struggles to nail her everyday sense of style. The former press secretary has battled her fair share of hard times, but none seem to be harder than finding an updated wardrobe to display on a daily basis. While there's been times McEnany has showed off her killer legs, it appears it might be a habit to possibly distract from her outdated outfits.

Like many other conservative women with zero flair, McEnany seems to appreciate blazers stuck in the 1980s, shoulder pads and all. She also has a penchant for grandma-inspired sweaters and other looks that should have possibly remained shoved in the back of her wardrobe. From a dress that looks like it took a ride on the Mayflower to cardigans complete with giant buttons, there's been plenty of times McEnany has appeared confused as to what year it is. Case in point, here are seven examples of McEnany boldly rocking some rather out of date trends.

Seen here in a February 2024 Instagram post dedicated to Kayleigh McEnany covering a special election, the blazer she chose was both outdated and a bit ahead of its time. While it looks like a vintage marching band jacket, it also is reminiscent of some of the outdated outfits White House press secretary Karoline Leavitt has been caught wearing. The cheap looking white fabric with bright fake gold buttons is distracting and feels like it crawled out of the 80s.

In an April 2024 Instagram post promoting her appearance on "The Five," Kayleigh McEnany tried to distract from rumors of possible plastic surgery by wearing a wild blazer. Looking at the image, the viewer can almost hear the sound her jacket would make every time she moved, which is a bold choice for someone on air with a hot mic. Not only is the color outdated, with hot magenta belonging in the 90s, but the double breasted buttons feel stuck in the 80s, making the whole look a bit of a mish-mash.

While the styling in this August 2024 Instagram post isn't the worst makeup mistake for Kayleigh McEnany, the choice of neon green grandma sweater certainly didn't help. The tennis ball brightness contrasts with McEnany's skin tone, causing her makeup to appear overly pink. The sweater itself is dated, with the fringed edges making it look like something a grandma would keep for special occasions. Plus, the tweed-like material woven in gray and green also gives the sweater a texture that looks like it belongs on a sneaker instead of a sweater. 

Adding to her surprising resume, Kayleigh McEnany was spotted in an August 2024 Instagram post, "broadcasting LIVE from the DNC!" While white is a color often associated with women's suffrage, here McEnany did herself dirty by wearing a top that felt like it came from the era of the suffrage movement. The muted cream of her buttoned up blazer-sweater combo doesn't match her pants, and the slit cuffs on the sleeves are confounding. Furthermore, the giant grandma brooch buttons make McEnany look as if she keeps hard candy in her purse.

In a November 2024 post on Instagram dedicated to "checking out our beautiful stained-glass set-up," Kayleigh McEnany dressed like she was expecting to walk into a time machine. The baggy black dress with white cuffs on the wrists and the pearled collar makes her look like she's ready for a trip on the Mayflower. Plus, her black tights and black boots give off an incongruent Wednesday Addams vibe from the rest of her 'fit, pulling McEnany in too many different directions.

Seen in this January 2025 Instagram post, Kayleigh McEnany is all smiles in her neon teal blazer that feels like it walked off the set of "Golden Girls." While there are plenty of strange things about McEnany, one of the harder things to ignore about her is how heavily her sense of fashion skews towards the 1980s. This blazer is a perfect example — the color feels like a beach house throw pillow, the shoulder pads date the look, and the brass buttons feel a bit costumey.

While promoting herself in a May 2025 Instagram post, Kayleigh McEnany wore yet another outfit that missed the mark. This black shirt is one she's been fairly fond of, having worn it more than once. At first glance the T-shirt appears fine, if not on the edgier side than what McEnany normally wears, however, the exposed silver grommets and lace-up details are decidedly dated. Harkening back to when shirts like this could be found in Express or Hot Topic, this look makes McEnany appear as if she just walked out of the mall circa 2010.