Kayleigh McEnany's Worst Makeup Fails Of All Time

We're used to seeing Fox News star Kayleigh McEnany looking glamorous. While we know Donald Trump's former press secretary is gorgeous without makeup, she doesn't often go bare-faced on TV. McEnany prefers full-coverage cosmetics, with her long lashes, glossy lips, and heavily defined eyes becoming a key part of her look. So much so that, sometimes, her appearance gets people talking more than the events she's covering on "Outnumbered." 

When McEnany shared an Instagram video urging her followers to tune in to her Fox News show in August 2024, several commenters seemed more interested in her cosmetics than her work. "I would hate to see your makeup bill," one person wrote in the comments. "Why so much makeup?" another asked. But even though McEnany clearly loves her glam (and there's nothing wrong with that) she doesn't always get it right. From too-dark foundation to poorly applied lashes, she's had her fair share of makeup fails.

There's nothing wrong with turning up the glam and wearing whatever makeup makes you feel comfortable, but Kayleigh McEnany's heavy look on Fox News in January had fans confused. In an Instagram video, the news anchor wore layers of full-coverage foundation that made her skin look unnatural, as well as dramatic, black liquid liner around her eyes. That was placed over a powdery, light pink shadow that blended into a darker shade on the outer part of her eyes. She completed the look with long, spidery faux lashes.

But she made a mistake applying her false eyelashes so they didn't quite match. On one eye, they were long all the way into the inner corner. However, the placement of the other made the strip lash appear shorter and flatter. That slightly changed her eye shape, making it look more elongated than round.

Fans noticed things were a little off, with many commenting on her cosmetics. "Why are you painting yourself up to look like a mannequin when you're a natural beauty?" one person asked. "You dont need all that make up ... You have that natural look ..." another wrote.

Kayleigh McEnany experienced a serious makeup fail in 2021 when she appeared in the White House briefing room without foundation above her lip. Snaps showed her speaking to the press with a patch above her mouth that was a completely different shade to the rest of her face, where she'd clearly applied foundation. McEnany or her glam team may have missed the area due to poor lighting or it could have rubbed off if she wiped her mouth or nose. It's also a possibility that McEnany or her team removed the foundation to perfect her lipstick or liner but forgot to reapply it.

One way to avoid making the same mistake is to check your appearance in multiple lights before stepping out the door. Sometimes, a simple change of location can reveal a mishap that dimmer lighting hid. A mirror with adjustable light settings — such as MIYADIVA 20X Magnifying Mirror with Light or Erlingeryi Store's 9" Lighted Makeup Mirror — can help you see your handiwork in different lighting scenarios.

In 2020, Kayleigh McEnany appeared during a White House press briefing wearing a slightly more understated look than her signature. She avoided cakey foundation and side-stepped dramatic, unblended eyeshadow, also opting for a flattering lipstick. But she overdid it with her super long strip lashes. The voluminous additions looked out of place with the rest of her makeup and would have been more appropriate for a night out than a daytime political event.

We're not saying McEnany shouldn't wear lashes during the day, but there are ways to do it that aren't so distracting. Using the right individual lashes would enhance her eye shape in a more natural-looking way, as individual clusters can be more easily customized for a less dramatic appearance. The likes of Ardell False Eye Lashes Faux Mink Individuals or KISS imPRESS Falsies False Eyelash Lash Clusters in Natural can be used to fill in gaps in your natural lashes, adding more hairs only where you need them.

We know, graphic and dramatic eyeliner was a trend in 2014, but Kayleigh McEnany took things a little too far in a snap posted to Facebook that year. She used a deep, black liquid or gel liner to define her eyes, applying it to the top and bottom lash line and her waterline. Though that can work for a high-glam, avant-garde look, it was so bold here it almost made the rest of her features disappear so her piercing eyes stole focus. Just, not in a good way.

Too much dark eyeliner, especially in the waterline, can be an aging makeup mistake because it can make the eyes look smaller (larger, brighter peepers are considered more youthful). Instead, makeup artist Ariel Lewis told us a softer, brown shadow can be more flattering. "Use a deep brown eyeshadow and an angled brush instead of a hard black kohl pencil. Keep gel liner away from the bottom. Use it only on the top of your lids," she said.

Kayleigh McEnany shared adorable, unfiltered family photos on Instagram in 2022 as she posed with her baby son Nash and daughter Blake. But unfortunately, it was her bad makeup that caught our attention most. The news anchor's foundation was too dull and orange, making her face multiple shades darker than her hands (which gave us Donald Trump makeup fail vibes). "You are as orange as your old boss," one person even commented. The foundation mistake aged her, as it made her skin look more like a mask than glowing and healthy.

But that wasn't McEnany's only faux pas. The outspoken political figure wore a pink lipstick that was so light her lips almost blended in with her skin, making her pout look flat. She needed to consider her undertone when choosing the right lipstick for her skin tone and could have benefited from a slightly darker lipliner to create more definition.