Kimberly Guilfoyle & Don Jr. Reach New Level Of Weird With Tacky Mismatched Outfits

Kimberly Guilfoyle and Donald Trump Jr. occasionally engage in cringey PDA, but they aren't one of those couples that dress alike. On the contrary — the disconnect between their outfits can be as vast as Kamala Harris and Donald Trump Sr.'s ideological differences.

In a photo that Guilfoyle posted on her Instagram Story, Donald Jr. is wearing a pair of gray slacks and a white untucked dress shirt with a curious detail. Zooming in, it seems that his initials are monogrammed in tiny letters right smack dab in the middle of the garment. Maybe he has to initial his shirts to keep his bro Eric Trump from stealing them — Eric did act like money was getting pretty tight by complaining about how much it costs to fill up his SUV in an appearance on Fox News. At least the "Jr." was there to let everyone know that the shirt didn't previously belong to Trump Sr. In a 2018 Extra interview, Donald Jr. said that his father often receives monogrammed items, which he then re-gifts to his oldest son. "There was one Christmas where he may or may not have given me the gift I had given him the year before because I had monogrammed it," he recalled.

Donald Jr.'s greige birkenclog shoes were also a choice — his cartoonish footwear looked like blown-up baby booties. As for Guilfoyle's latest odd outfit, it wouldn't have been so bad, save for one detail.

Perhaps Kimberly Guilfoyle and Donald Trump Jr. went on a romantic fall date to Spirit Halloween, because her outfit could have been a packaged Elvira knockoff costume bearing a name like "Evilia, Bat Mistress of Midnight." It had a deep neckline, which would surely meet with the Queen of Halloween's approval. However, Guilfoyle's skirt was only knee-length.

Without the accessory around her neck, Guilfoyle's outfit wouldn't have been quite so Halloween-coded — but the massive silver cross made her overall look unequivocally goth. Of course, no real vampire would dare wear such a pendant, lest they repel themselves. When Guilfoyle had to beg for applause during her speech at the Florida GOP Victory Dinner, she appeared to have the same necklace on.

Guilfoyle's dark makeup and long fingernails also read a bit Morticia Addams, but what's going on with her missing thumb? Did Wednesday trick her into sticking her hand into Pugsley's mini-guillotine? It's unclear what type of event she was dressed for, but the man sandwiched between her and Donald Trump Jr. is Sticker Mule co-founder Anthony Constantino, who upset many of his employees and customers by announcing that he's a Donald Trump supporter on Sticker Mule's X account. "I am appalled at the use of the company in this way," one employee told Forbes. If Constantino hoped his controversial public show of support would earn him a ticket to Trump world, it looks like he was right.