Kimberly Guilfoyle isn't known for her subtlety, either when delivering loud, bombastic speeches or when it comes to her makeup. Specifically, she's notorious for her dark, heavy-handed eyeliner and eyeshadow choices that look like she's taking style inspo from a particularly glam raccoon. Looking back on past years and her time in the political spotlight, it's clear that Guilfoyle's makeup style has completely changed over the past two decades , with her look getting much darker, bolder, and more dramatic.

However, back in April 2024, before Guilfoyle called off her engagement to Donald Trump Jr. , she and her then-fiancé shared a date night at the Wags To Riches Gala in Palm Beach, Florida. Guilfoyle took to Instagram at the time to share a slideshow of snapshots from the event,

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