Kimberly Guilfoyle & Donald Trump Jr.'s Worst Couples Outfits To Date

Kimberly Guilfoyle and Donald Trump Jr. are the GOP's power couple. They electrify and energize the MAGA masses at rallies across the USA with fiery and ferocious rabble-rousing speeches. Despite Guilfoyle's relationship and subsequent divorce from Gavin Newsom, a lifelong Democrat and current California governor, her politics align perfectly with Trump's. However, on a separate, non-partisan note, their sense of style is sadly not aligned. In fact, there's a case to be made that Guilfoyle and Trump wear some of the worst couples' outfits in politics and beyond.

The list of Guilfoyle's inappropriate outfits is seemingly endless. The mom-of-one loves to go full-out glam, exposing her tanned and toned legs and ample chest on every occasion. Whether it's a trip to the market (let's face it, that's never), a fun family day out slaughtering animals in the wilderness, or a political soiree, Guilfoyle never misses an opportunity to add some va va va va voom.

Guilfoyle's homecoming dance look on the campaign trail in April 2024 was as divisive as her political ideology. In a low-cut LBD, she stole the spotlight, leaving little to the imagination. She added a matching black rosette choker for maximum impact. Meanwhile, Trump prefers the Gap, Target, and Sears soccer dad aesthetic of chinos and shirts or full-on camo from Big 5 or Dicks. And, of course, boardroom and courtroom-ready suits. It's definitely a stark style contrast, but how badly so? We're looking at Guilfoyle and Trump's worst couples' outfits.

Kimberly and Don Jr.'s Carnival catastrophe

Kimberly Guilfoyle and Donald Trump Jr. wore one of their worst couple outfits for a family night out at the carnival in December 2023. The two were accompanied by four of Trump's five kids. Guilfoyle had a great time and gave shout-outs to the carnival organizers, who'd presumably rolled out the red carpet. "Don Jr. and I had an incredible time at the @admiralscovelife carnival last night with our kids! @admiralscovelife; you really outdid yourselves this time. We cannot wait until next year!" she wrote on Instagram.

Guilfoyle also posted a carousel of pics from the night, and quite frankly, it looked like she, Trump, and the kids all attended a totally different event. Trump and the children were dressed in casual shirts, T-shirts, sweats, and shorts, just like you'd expect to wear on a trip to the fair. But Guilfoyle? Well, not so much.

She was glammed up to the nines, looking ready to dine on moules frites at ​​Balthazar rather than chow down on a shady hotdog and cotton candy. Guilfoyle's thigh-skimming hemline ensured she wouldn't be mounting anything at that carnival. Her sparkly clutch bag and sky-high heels were also not so carnival-friendly. Guilfoyle ensured everybody knew precisely what she wore though in her post-credits: a Balmain dress, Christian Louboutin pumps, and a Trump Store purse. Sadly, no word on where Trump's grotty green shirt was from.

Kimberly and Don Jr.'s Bahamian baecation

Kimberly Guilfoyle and Donald Trump Jr. know how to enjoy Independence Day in style. No bonfires, BBQs, and fireworks for this couple. Instead, they jetted off with the kids to the beautiful Bahamas in 2023. "A fun getaway with my love, @donaldjtrumpjr, and a special 4th of July celebration with our family," Guilfoyle captioned a carousel of pics, along with three heart emojis and two hashtags: #baecation and #bahamas. The Atlantic lamented the death of the word "bae" in 2014. Still, you can't expect Guilfoyle and Trump to be aware of that.

However, it wasn't just the cringe mid-aughts teen slang that stood out. Guilfoyle and Trump also had one of their worst couple outfits on display. In the first of Guilfoyle's pics, Trump is seen awkwardly hugging Guilfoyle on what looks like a boat. He's dressed like he's setting off to film "Deadliest Catch" with an old baseball cap, chinos, and creased striped shirt. While Guilfoyle appears camera-ready for a "Real Housewives" taping, resplendent in a strapless green dress, long locks perfectly styled and flowing.

In another shot, Guilfoyle ups the ante on the fun family getaway by posing as Lisa Vanderpump in a red couture dress, gold heels, and a pampered pooch under her arm. Meanwhile, Trump took "Deadliest Catch" to the next level by treating a glammed-up Guilfoyle and casually dressed boys for a fishing trip where they landed a suitably huge king mackerel.

Kimberly and Don Jr.'s disco ball dichotomy

Kimberly and Donald Trump Jr. debuted one of their worst couples outfits to date in March 2024. "In each other's corner, taking on life together head-on with determination and dedication," Guilfoyle captioned an April 2024 Instagram shot of the two, who looked like they were in entirely different types of corners in completely different places.

Guilfoyle was ready for a night out at Studio 54 — well, she would have been back when it was still open. She was clad in a shimmery disco-ball style €2,450 Retrovête Kaleido dress (approximately $2,618), matched with a gloriously perfect pearl choker. Meanwhile, Don Jr. looked ready for a parent-teacher conference at one of his five kids' schools, dressed in a navy suit that looked like it'd been hired from Men's Wearhouse, along with a shirt that was too small to button up properly at the top.

Guilfoyle and Don Jr. were not just making an ill-matched outfit statement, though. They were also taking on life together at the 40th birthday party for Donald Trump's hard-working attorney, Alina Habba. They were joined by Melania, Eric, and Lara Trump. Guilfoyle had posted another pic of her dress a few weeks earlier, showing her flanked by Lara in a conservative red dress and Habba in a tan sparkly jumpsuit.

Kimberly and Don Jr.'s celebratory contrariety

Kimberly Guilfoyle and Donald Trump Jr.'s couples' outfit was definitely out of synch in January 2023. The two were heading out to mark Trump's big day, as he'd turned 46 years old on December 31, which made for a perfect celebratory twofer as Guilfoyle and Trump reportedly got engaged on December 31, 2020. "Tonight was extra special celebrating @donaldjtrumpjr's birthday. Don, you are strong, smart, courageous, funny, and the love of my life. I can't wait to spend the rest of our lives together. Love you," Guilfoyle posted on January 1, 2022, her massive sparkler on full display.

"Simply the best! Happy Birthday and Happy Anniversary, sweetheart. You are my treasure! Love you to the moon and back. From our family to yours! Happy New Year! Much Love and God Bless! XO KG and Don," Guilfoyle captioned a January 1, 2023 pic of the happy couple, who looked like they had decidedly disparate ideas regarding what constituted the perfect birthday celebration.

Trump was dressed in a sateen-looking baggy white shirt over shapeless jeans, looking like he'd love to kick back, watch the game, and sink some brewskis with the bros. However, Guilfoyle looked full-on femme fatale, ready to slay some dudes and break a few hearts, clad in a gorgeous, black, skin-tight, butt-skimming sparkly dress and gold high-heeled sandals.

Kimberly and Don Jr.'s Christmas contradiction

Kimberly Guilfoyle and Donald Trump Jr. rang in the holidays with one of their worst couples' outfits to date. "We are extremely grateful for this Christmas and all of the joy that it brings. Here's to a season filled with love, and looking forward to the new adventures that the upcoming year holds," Guilfoyle captioned a December 26, 2023 photo of the spouses-to-be dressed in their Christmas finery.

In fairness, they both did look fine. Trump brushed up nicely in a black suit, white shirt, and red tie —although the jacket's sleeves looked a tad too short. Meanwhile, Guilfoyle was dressed to the nines in a tiny black mini-dress cut away from under the chest and replaced with a front-tied bustier edged in sparkling silver. She completed the look with a glamorous, bejeweled glittery hand purse, a beautiful statement ring, and perfectly styled hair. True to form, Guilfoyle ensured everybody knew who created her outfit: dress by Self-Portrait, bag by Dolce & Gabanna, and ring by Cameron Patrick Neth.

Finesse aside, though, it just leaped out at how incredibly mismatched the couple's outfits were. He looked ready for the boardroom, while she looked fit for the ballroom. This leads one to wonder if Guilfoyle and Trump are also mismatched in reality. Over the six years they've been together, they've busted out with more than their fair share of the worst couple outfits. But, well, they do say that opposites attract.