Trump Jr.’s Casual Look Contrasts Guilfoyle’s Dress in Odd TikTok Video

Kimberly Guilfoyle and Donald Trump Jr.’s cringe-worthy moments have been occurring since they started dating in 2018. They added to that list with their recent appearance at a Trump boat party in Jupiter, Florida, the weekend before the Democratic National Convention (DNC). Guilfoyle posted a video of the event on her social media pages, and she and Don Jr. are seen waving at people in their boats.

There are a couple of things that stand out in the video. To start, Don Jr. was looking super casual in a drab olive t-shirt and what looked like chino shorts. It’s giving divorced dad vibes, and it seemed to fit in well at a boat dock on the middle of a sunny August day. But it doesn’t seem like he and Guilfoyle were at the same event.

@kimberly.guilfoyle

The next MAGA boat parade is October 13th! 🛥️🚤🇺🇸 @donaldjtrumpjr @President Donald J Trump

♬ Good Time – Owl City & Carly Rae Jepsen

Guilfoyle was in full glam makeup wearing a low-cut black and red patterned dress with a thigh-high slit on one side; however, she seemed to be both showing off skin and too covered up since she paired it with a black jacket or cardigan. She must have been literally hot, as the weather in Jupiter on August 18 was up to the low 90s with over 50% humidity. Not really black layer weather.

While Kimberly Guilfoyle’s outfit seemed inappropriate for the setting, especially when compared with her fiancé Donald Trump Jr.’s look, we have to give it to her, she wasn’t wearing heels. Guilfoyle’s had wardrobe malfunctions in the past, so perhaps she didn’t want to risk another one by losing her footing as she celebrated Donald Trump.

Later in the video, we see Guilfoyle on a boat where heels are definitely a no-go; she also ditched the black layer onboard. But while she’s in the boat, Don Jr. is still on the dock. Why he was left behind (and if it was for the whole event), we don’t know, but it’s another odd aspect of the video.

A third thing people found weird was when Guilfoyle and Don Jr. cheered for boats flying the American flag upside down, which has long been a symbol of distress. One person on X, formerly known as Twitter, wrote, “Flying the American flag upside-down has become a pro-Trump symbol. It is also used by elections deniers. It is deeply offensive and unpatriotic.”

Eric Trump was also there and he posted a video from the event. While the boat parade seemed to highlight pure support for Donald, on both Guilfoyle’s Instagram and Eric’s, some commenters asked them to tell Donald to stay on message and stop with the name-calling and personal attacks.