Kayleigh McEnany Has Worn Some Woefully Outdated Outfits

Like most people who have worked in the Trump administration, Kayleigh McEnany struggles to dress for the decade in which she's living. Similar to the current White House Press Secretary, Karoline Leavitt, whose outfits continue to miss the mark, McEnany — who once had Leavitt's job — also can't seem to get it together. Whether it's neon dresses and blazers that would make 1980s' Barbie blush in embarrassment or her never-ending affinity for tacky accessories like glitzy, gaudy buttons, no matter which way McEnany turns she has yet another outdated look she's trying to make happen. Sadly, she just continues to fail.

Why it is that so many MAGA women are so unable to be fashionable, frankly, seems like it should be studied. If it were just one or two of them, then it could be considered a blip. But from Lauren Boebert's outdated denim trend to Melania Trump's biggest fashion fails, Robert F. Kennedy, Jr. may want to get someone to test the water at the White House and see if Pete Hegseth accidentally dumped some of his gin into the supply lines.

Although McEnany isn't officially at the White House anymore, she is a talking head for Fox News, and since they're all batting for the same team, there's no sense in categorizing them separately. If you want to make darn sure you never find yourself in a woefully outdated look, then McEnany's outfits are what you want to avoid.

In 2013, exposed zippers, especially on women's clothing, were a hot trend. Whether the zipper was up the back, in the front, along the side, both high-end designers and fast-fashion labels were all about making zippers seen at every corner. While it was cool for a hot minute, because it was so overdone, the trend got old fast and faded into oblivion — that is for everyone except Kayleigh McEnany. In fact, not only is McEnany still hanging on to this trend, as seen in this photo, a jaunt onto her Instagram page shows she has her claws dug into the exposed zipper trend of 2013 so deeply that she definitely won't be giving it up anytime soon.

As much as Y2K fashion trends had a lot to offer, some of which are worth revisiting, certain things should be left in the early 2010s — most notably color blocking. Big, bright, bold colors blocked together in different shapes wasn't an easy look to pull off when it was in fashion, and it's even harder now that it's passé. Yet, like exposed zippers, Kayleigh McEnany is knee-deep in color blocking dresses and it's not just outdated, but not doing her any favors. If Victoria Beckham couldn't successfully bring color blocking back in 2021, then McEnany certainly can't do it now or ever.

When covering the DNC in August 2024, Kayleigh McEnany decided to go way back to the 1990s with her look. While the 1990s was a big time for the grunge fashion trend thanks to the explosion of bands coming out of Seattle, especially Nirvana, for those who were more into the Limited Too aesthetic, bedazzling was all the rage. But the problem with the bedazzling trend — and nothing was off limits when it came to tacky glitz and glimmer — is that it's a look that these days very quickly shows just out outdated you are in your fashion choices. What's even worse is that this shirt looks similar to Kimberly Guilfoyle's infamous Forever 21-looking top, and that's something everyone should avoid like the plague it is.

What we have here, with this sleeveless denim top, is a fashion faux pas on two levels. First of all, sleeveless denim, whether it's a top, a vest, or a dress, hasn't been a thing since the 1990s. Secondly, as Kayleigh McEnany is probably aware since all the MAGA women share the same sense of style, it's looking very much like that republican vest trend we've been wishing would end. To add insult to injury, McEnany wears this top again and pairs it with a white blazer — no joke — and it looks just as ridiculous as it sounds.

When it comes to the essentials for rocking the emo look, you need a lot of black, a pair of Doc Martens, and a whole boatload of studs and grommets. Here, Kayleigh McEnany has a shirt with grommets, but it's safe to say she's not wearing Doc Martens on her feet, nor has she ever even heard of Sunny Day Real Estate, let alone owns an album by them. Once we calculate the figures on these stats, not only is McEnany dressed for the wrong decade, but she's also dressed for a genre that's way over her head.

Remember that deliciously adorable scene in "Barbie" when the titular character and Ken are dressed in all neon and rollerblading throughout Venice Beach, and people keep staring because — ouch! — neon hurts the eyes? Of course, you do. Even Margot Robbie told Jimmy Fallon on "The Tonight Show with Jimmy Fallon" that she was mortified to be seen by so many people while wearing the flashy getups. Why? Because neon belongs in the 1980s where it can't hurt anyone. However, Kayleigh McEnany clearly believes otherwise and this neon blazer is just one in her very long list of neon moments.

In November 2024, Kayleigh McEnany checked out a stained glass promotional set up in New York City for "The Saints" on Fox. Not only was she channeling Wednesday Addams, most likely accidentally, but the contrasting collar and cuffs are a throwback to the early 2000s, as are the platform boots she appears to be wearing. Not only is the shoe style so outdated that it's aging McEnany, but she also looks like a child playing dress up. While there's nothing wrong with wearing clothes that are a blast from the past, what matters is that you know it's retro. But with McEnany none of her choices are homages to decades long gone, but rather the fashion decisions made by a woman who's clueless, deluded, and missing the plot entirely — like so many others over at Fox News.