While her wardrobe may be totally stuck in the past, Guilfoyle’s life is moving forward.
Donald Trump has also nominated her as the new U.S. ambassador to Greece.
First on the docket?

That would be her penchant for wearing out-of-date looks.
Still, Guilfoyle somehow managed to sport this classic outfit in a way that was majorly out-of-style.
Guilfoyle wore a white blazer with dark jeans to the Super Bowl in 2020.

At this time, skinny jeans were already on their way out.
This look is so Kim Kardashian in 2010.
Unfortunately, Guilfoyle did not wear this dress in or around 2010.

She actually wore this to wish her Instagram followers a “Happy New Year” in 2024.
Nothing about this look is really working.
The color washes her out and feels off-trend.

A year prior, in January 2023, she went for a similar, equally outdated look.
She sported another long-sleeve minidress this time with even more garish bedazzling.
Once again, this look wasn’t at all modern enough for when she chose to wear it.

As she is wont to do, she also managed to make it even worse with her styling.
Leave it to Kimberly Guilfoyle to sport it a decade later.
In 2018, though, low-rise was firmly out, and high-waisted garments were in.

It’s both business casual and strangely revealing.
If the top was slightly longer, this would have worked for a day at the office.
As it is, though, this outfit basically doesn’t work for any occasion we can think of.