Kellyanne Conway's Makeup Is Always An Unglamorous Affair

During the first presidency of Donald Trump, it was nearly impossible to avoid his senior counselor, Kellyanne Conway. Though there's much to know about Conway, she certainly made it clear that she enjoys being the center of attention. Of course, her position was one that included communication, and there's reason to believe that Trump prefers his administrations to be televised, but Conway did find ways to get on camera fairly often. For someone so boldly in the public eye, it would make sense that Conway would want to ensure a fair amount of care went into her glam routine. However, much of her makeup choices would suggest otherwise.

Considering the close relationship between Conway and Trump, and how he most likely prefers people in his orbit to appear in public, it's a mystery as to how often Conway left the house looking disheveled. From habits she needs to break, like excessive under eyeliner, to overly slathered on foundation, there have been plenty of times Conway avoided glam while possibly being in search of it. Though the Mar-A-Lago face trend was after her time in the White House, Conway still managed to set the stage for much of its aesthetic. From chunky mascara to overdone blush to too much foundation, there's ample evidence to suggest that Conway's makeup has always been a bit of a disaster.

Though Kellyanne Conway is known for not holding back her disdain for powerful people, she might want to hold her makeup blender a bit longer. In the above photo from 2016, Conway is caught speaking to reporters in Trump Tower with her nose showing signs of her makeup having been rubbed off. This is odd because the rest of her face appears to be caked on with foundation, especially under her eyes. Conway also overdid it with the mascara and under eyeliner, two trends that she can't seem to shake, no matter how out of date they are.

While skulking the halls of the White House in August 2017, Kellyanne Conway once again showed off a rather unglamorous look. Not only is her hair flat and wispy, adding a heaviness to her face, but her makeup is caked on. It's a look that feels both intentional and slapdash, possibly due to Conway's lack of eyebrows, calling into question whether she forgot to draw them on. Her under eyeliner is more bold than her mascara, which unfortunately accentuates the creases under her eyes. It also looks like she forgot to put on any blush, making her whole face feel matte and flat. 

Similar to the fashion fails Kellyanne Conway will never live down, so too goes her makeup in the above photo from October 2018. Perhaps Conway thought she was getting glammed up to give an interview, but her styling lacks finesse. The makeup around her eyes is cakey at best, and her consistent under-eye liner is a habit she should consider dumping. Conway's lip color also doesn't feel fully thought through, though it matches her blush nicely. However, the overall look is thrown into more chaos by her chunky, questionable hair.

Though Kellyanne Conway has no problem lashing out at former colleagues, she might want to figure out a better trick for getting her lashes to stick. In the above photo from 2019, her most likely fake eyelashes feel like they're ready to detach, and the rest of her makeup looks soggy. It appears as if Conway was reaching for glamour with her pink top, but her lipstick failed to match the look. Conway's under-eye liner adds a level of heaviness to her, which is unfortunate as her foundation is already packed on.

Seen giving remarks at a press conference in 2020, Kellyanne Conway overdid it with the blush. Her cheeks and nose are overly red, making her appear as if she's been standing in the cold. This is accentuated by her lip color, which adds a maroon note to Conway's overall look. Her glommed-on mascara is way too chunky, and her under-eye line draws attention to some wrinkles in an unflattering way. Conway's caked-on foundation also gunked up the creases between her wrinkles, overstating them instead of smoothing them out.

Though she's not part of Donald Trump's second administration, Kellyanne Conway has still found a way to keep herself on television screens. While hosting her own show in 2024, "Here's the Deal with Kellyanne" on Fox News, Conway once again displayed some dire makeup mistakes. Conway appeared to have had some possible work done, with her lips looking a little fuller and her forehead smoothed out. However, her eyes still boast a cakey disaster, and her white eye shadow feels stuck in the 90s. Even with a bit of a facial refresh, Conway is still stuck in the past with her makeup trends.