13 of Kimberly Guilfoyle's best and worst looks

The vibrant shade of this knee-length, short-sleeved dress was a strong choice for Guilfoyle, who accessorized with snakeskin pumps.

One month later, Guilfoyle started dating Trump Jr., Page Six reported. They went Instagram official in June, and she joined him at the Montana Republican Convention that same month.

Guilfoyle loves a knee-length dress, and while this one was largely elegant, the belt made it seem old-fashioned. The look would've been more streamlined without it.

Her red heels also blended with the red carpet.

This look, which she wore to an event in the Hamptons in May 2018, had too much going on.

The blouse clashed with the trousers, which in turn clashed with the geometric-patterned heels.

Her necklace, which appears to feature a chili-pepper pendant, also didn't gel with the rest of the look.

A slightly less plunging neckline or a subtler mesh overlay would've made this look more cohesive.

Instead, the illusion of a vest and skirt made it look like menswear or officewear, which, in Guilfoyle's defense, Gen Z now loves.

While it was refreshing to see Guilfoyle stepping away from her typical closed-toe pumps, it's a fashion faux pas to wear pantyhose with open-toed shoes.

This appearance in August 2018 — to attend the Washington, DC, premiere of political documentary "Death of a Nation" — was one of Guilfoyle and Trump's first public appearances as a couple.

In August 2018, Guilfoyle attended the annual summer party for New York's Stony Brook Southampton Hospital, where she was pictured with publicist Matt Rich.

She wore a red dress for the event, but the look would've been much better without the fur across the chest — the red lace overlay was enough of a statement.

For a New York Fashion Week event for designer Chiara Boni (pictured left) in 2019, Guilfoyle wore one of Boni's designs.

Guilfoyle accessorized with long diamond earrings and later added a black cape to her look.

The outfit could've been improved with black pumps — white heels are a tricky thing to pull off — although Guilfoyle's Valentino heels did complement the white in her dress.

You might not be able to tell, but this Zang Toi dress Guilfoyle wore to the designer's fashion show in 2019 was almost completely see-through underneath bright lights and flashing cameras.

If it weren't for that unfortunate design flaw, it wouldn't be too bad — though we could do without the butterfly embellishments on the shoulder.

It happens to the best of us, but this is a good reminder: always do a flash test before going to an event with lots of cameras.

The slit in her orange skirt is subtle, and it pairs well with the yellow ruffled blouse. While the look could've been elevated with different shoes — why leopard-print heels? — this is a solid look.

Guilfoyle wore the knee-length, Republican-red dress to deliver a fiery speech at the Republican National Convention.

The dress, which has an orange undertone, was a striking look for Guilfoyle. The only improvement to the look could've been a simple necklace.

While another striking color to help Guilfoyle stand out on stage, the shade of green made this dress look dated.

That was also the case for the business-casual peplum, which hasn't been on trend in years — though some designers are trying their hardest to bring it back.

Guilfoyle wore this dress to CPAC in February 2022 and again in April for a meeting with the House Select Committee investigating the attack on January 6.

While navy blue works better with this peplum style, we can't ignore the crystal-encrusted heels, which feel out-of-place for the setting.

This geometric minidress by Balmain wouldn't have been out of place in season one of "Keeping Up with the Kardashians," but it doesn't fare as well in London in 2024, where she was spotted with Donald Trump, Jr.

Once again, we would've preferred to see her pair this with black heels, not bright-white ones.

This Badgley Mischka dress is an understated, elegant look from Guilfoyle.

She also didn't over-accessorize, choosing just a pair of chunky silver earrings.