Kimberly Guilfoyle's Sneak Peak Into Outdated Glam Routine Shows Don Jr. What He's Missing

The higher the hair, the closer to ... moving to Greece to get away from your ex? Donald Trump Jr.'s ex-fiancée and President Donald Trump's pick to be the US ambassador to Greece, shared a look to her Instagram Story in February 2025 that once again took us back to Y2K.

In the mirror selfie, Guilfoyle is rocking her signature chestnut extensions to pair with a dramatic, smoky makeup look and a mauve lip. Then, at the top of her head, there appears to be a bird's nest heightening her hair a few inches, and may even make her taller than her famous ex Don Jr. — who stands at 6 feet, one inch tall, for those wondering.

We suspect that Guilfoyle might have her hairdresser employing a hair height-enhancer like a Bump-It (yes, you can still buy them today). You know, that little plastic accessory that young women would probably tease their hair over before a Nickelback concert in 2005. Since it seems Guilfoyle is once again relying on an accessory of the past, it might be about time that she studies up on current hair trends.

Kimberly Guilfoyle just can't seem to get it together in the hair department; we even edited her without her super-long extensions, and she looked stunning. The least she could do is make them appear more cohesive with her natural head of hair or opt for hair that doesn't go down to her hips, but it doesn't look like she'll be taking notes from us anytime soon, though.

Back in January 2025, Guilfoyle posted a photo to Instagram of herself and Donald Trump walking into the White House before his inauguration, and we can't help but focus on one tiny detail. The photo is of their backs, and her hair alarmingly only reaches a few inches past her shoulders. It looks a bit fried and in need of some oil, meaning that the strain, heat, and wear she adds to her mane really can't be doing her much good. We hate to say it, but it might be time to hang up the 20-inch tape-ins.