Paris Hilton's Most Glaring Makeup Mistakes Of All Time

Very few celebrities managed to captivate and define an era quite like Paris Hilton in the early 2000s. The Hilton Hotel heiress has proved she has some serious business prowess of her own, walking the runway for New York Fashion Week, starring alongside fellow "celebutante" Nicole Richie in their "The Simple Life" reality TV show, launching her own product and perfume lines, and even taking the stage with her music and DJ careers. While the entrepreneur is no stranger to the glitz and glamour, she's also devoted time to some philanthropic work, including working with charities aiding children and cancer patients. However, although the socialite's heart has seemingly been in the right place, her makeup brushes haven't always been.

Hilton's wardrobe has been nothing short of influential (aided in part by her former wardrobe assistant, Kim Kardashian), but her makeup has missed the mark on more than one occasion. The queen bee has been in picture-perfect condition over the last couple of years thanks to a more reliable glam squad, but even her more polished look can't distract from her most glaring makeup mistakes of all time. The mom of two better hope that her daughter, London, learns from her unforgettable false lash faux pas and bronzer blunders.

While false eyelashes on the lower lashline have always had their place, there's a fine line between enlarging your eyes and weighing them down. Paris Hilton seemingly got those lines mixed up in 2003 during the 75th Academy Awards, donning a fully flared-out falsie on her bottom lashes in addition to a heavy top set. Brit + Co specify in their instructions for the best bottom lash application that the length of the false set should be cut shorter, or else they'll "look insane." The proof is in Hilton's pudding, apparently, as the full set has her looking more avant-garde than award-ready.

While Paris Hilton was all smiles at the Hugo Boss Sundance Film Festival afterparty in 2001, her grin revealed a classic makeup mistake that nobody is immune to: lipstick stains. Her flared-out purple eyeshadow wasn't the only element of the look that went out of bounds, as traces of her metallic pink lipstick smeared across her top row of teeth. While her photo buddy remains unidentified, she was in clear violation of girl code for seemingly not telling Hilton about the makeup misstep.

Pictured in 2003 next to Calum Best after walking the LA Mercedes-Benz fashion show, Paris Hilton looked far from her best with her smokey cut crease and red lip. The off-kilter eye look might have worked well on the runway, but post-show was giving more rags than riches. Clear smudging under and in the inner corner of her eye had her eyeshadow looking worse for wear. A neutral nude was chosen for the original lip, helping not to overshadow the already bold look. Now the two elements were left to fight for dominance on Hilton's face, creating a loud but rather lukewarm finished product.

Paris Hilton's look at the 2003 Jeremy Scott fashion show might have been an homage to a Gillette razor, but the cutting edge look seemed a little too sharp. Paired with a heavy tan and pixie cut, the cool-toned, winged silver eye makeup clashed violently with her complexion. With a thin brow hanging over head, this particular makeup mistake has been emblematic of one of the most questionable Y2K trends: frosted eyeshadow. The frosty look might have sought to give Snow Queen, but it unfortunately falls a lot closer to Tin Man glam.

While heavy bronzer was all the rage at the turn of the century (and is making a devastating comeback with White House staff), Paris Hilton couldn't quite follow through with it when arriving at The Latin Lounge Club in West Hollywood in 2003. The uneven application left unblended made her look like she painted her makeup on haphazardly before heading out for a night on the town. Maybe the lighting did her no favors, but paired with a messy smokey eye, this look undoubtedly has become a dark stain on her cosmetic reputation.

Paris Hilton's GQ Lounge birthday party in 2002 was undoubtedly a night to remember — although the socialite might hope you could forget her eye look. While Twiggy popularized the drawn-on lower lashes in the '60s, Hilton's modern take on the trend looked overdone, with the muddy mess of eyeliner overpowering her lighter, natural brows and lashes. The sharp spikes seemed rather patchy at their thicker points. Less "Belle of the Ball" and more "Anime character gone rogue," the birthday girl would have done better with a softer look to complement her baby pink ensemble.

Paris Hilton's makeup at the "Exit Wounds" movie premiere in 2001 was a bold panda-like eye look emphasizing her bright blue eyes in all the wrong ways. Besides tapering out into a rather awkward, rounded end, the dark color made Hilton's ocean-colored eyes look like colored contacts, giving the star an artificial, uncanny vibe. The standout eyeshadow worked better when paired with her iconic 21st birthday look, but her star-studded outfit for the premiere made the heiress look out of this world (and not in a good way).