10 Times Kimberly Guilfoyle Dressed For Revenge After Don Jr. Split

A political advisor seems like the perfect match for the president's son, so we expected Kimberly Guilfoyle and Donald Trump Jr. to last as a couple. The pair began their relationship in 2018 and became engaged in 2020, but in 2024, things got rocky. While Don Jr. was first romantically linked to socialite Bettina Anderson in September 2024, confirmation of his split with Guilfoyle didn't come until December that year. It can be hard to navigate the holidays while going through a breakup, but at least the timing ensured that Guilfoyle could spend a new year showing Don exactly what he was missing with her wardrobe.

To be clear, there's been no public animosity between these two exes, with a source telling People at the time of their breakup, "It's an amicable split. It's not one that is going to blow up, at least at this point." But whether Guilfoyle and Don Jr. are on good terms or not, we love to interpret fashion as a source of communication. Clothes say things we can't utter out loud, after all, and that's exactly what revenge fashion is. When you dress in a way that shows the world you're better off post-breakup, while also perhaps stirring a little desire in your ex, you get the last laugh regardless of how the split played out. Princess Diana's black revenge dress became one of the most iconic looks in fashion history following then-Prince Charles' admission of his infidelity, and since then, countless women have followed suit.

Before her breakup — and appointment as the U.S. ambassador to Greece — Guilfoyle sometimes opted for tight and revealing clothes. While some of her revenge looks have maintained that theme, others embody elements like success, fun, and power, sending a subtle but certain "checkmate" to her ex.

In May 2025, five months after her split from Donald Trump Jr., Kimberly Guilfoyle attended the elegant amfAR Gala in Cannes, France, and her look had more than a few eye-catching elements. The bold red hue alone made Guilfoyle the star of the show, which is one of the best ways to get revenge, if you ask us. Then, there was the plunging neckline, which Guilfoyle seems quite comfortable with. Finally, the sheer, embroidered lace cemented this look as one for the ages. 

Donald Trump Jr. may have been the first one to move on romantically, but Kimberly Guilfoyle appeared to have the last laugh when she officially stepped into the role of U.S. ambassador to Greece in September 2025. Guilfoyle jumped right into the new position, culminating three months later in her appearing as an actual Greek goddess on the cover of Grace Magazine. Along with looking like Aphrodite reincarnated, Guilfoyle was also in head-to-toe white, perhaps showing Don Jr. what he was missing after the cancelation of their engagement. 

Revenge fashion usually summons images of short hemlines and low-cut tops, but it can also involve dressing modestly. Sometimes, revenge is less about sex appeal and more about power, as Kimberly Guilfoyle demonstrated in November 2025, when she turned up for an official meeting at the Presidential Palace in Athens, Greece. Nearly a year on from her split with Donald Trump Jr., Guilfoyle was letting the world know through a boss-babe pinstripe suit that she no longer needed him. (P.S.: Here are our tips for rocking pinstripes outside the office.)

Sometimes, revenge fashion is more overtly sexy, which is why red is such a common color in post-breakup outfits. While attending the Hellenic Initiative's 9th Annual Gala in London, England, in October 2025, Kimberly Guilfoyle opted for an in-your-face long-sleeved dress with mesh detail. The see-through features gave glimpses of her arms and thighs, and the intense color ensured once more that the ambassador was commanding attention after her split. While her wardrobe is perhaps a little loud, she has the perfect evening makeup for a black-tie event.

Black is the color most associated with revenge fashion (thanks, Princess Di!), but white also plays an important role. Specifically, it gives snippets of what a bride would have looked like on her wedding day if the engagement had lasted. Unfortunately for Donald Trump Jr., snippets of a white-clad Kimberly Guilfoyle were all he was ever going to get, and that was made clear at the Grand Prix in Monaco in summer 2025. Guilfoyle appeared on her balcony in a white two-piece that also flashed her stomach.

One of the goals of revenge dressing is to let your ex know you're better off without them, so outfits that embody fun are apt. Kimberly Guilfoyle went the playful route at a wedding in Italy in June 2025, pairing a pink silk dress (with an irresistible cutout, mind you) with a fluffy baby-pink jacket and what appeared to be a studded Valentino handbag to match. The sartorial version of the song "Girls Just Wanna Have Fun," this 'fit let everyone know that Guilfoyle was living her best life half a year post-breakup.

Since becoming the U.S. ambassador to Greece in September 2025, Kimberly Guilfoyle's wardrobe seemed to become more professional and corporate-coded. However, before she successfully put her own spin on corporate wear, she embraced her sartorial comfort zone in April 2025 with a pink minidress that had a sequined collar and cuffs to boot. This was a fun look for a party, but more importantly, four months out from her split, it showed off her figure and drew the eyes of the room.

The mother of all Kimberly Guilfoyle revenge outfits had to be the dramatic black gown she wore to receive the Cigo Award for the nonprofit animal organization Furry Friends Jupiter in March 2025. This dress had all the stops: a glamorous train of feathers, plumed shoulder pads with dangling beading, a drop-waist bow, and a lace bodice with a plunging neckline that resembled lingerie. It would have been quicker to tell Donald Trump Jr. to eat his heart out, but this way was likely more fun.

Gold represents winning, and when you combine that with sparkles and bling, it can only mean that a woman is thriving in life. So, we'd wager a guess that the sparkly gold minidress Kimberly Guilfoyle wore in March 2025 to celebrate her birthday was intentional. "Feeling grateful for another year of life, growth, and amazing people by my side," she wrote in the caption of her Instagram post. "Here's to new adventures, laughter, and making the most of every moment!" Translation: "I'm better off without you, Don Jr."

In March 2025, three months after her breakup with Donald Trump Jr., Kimberly Guilfoyle showed off her killer legs in an elegant white tweed mini to an event in support of the Big Dog Ranch Rescue. Between the white bridal shade and the skin on display, we're guessing that this look gave the POTUS' son a lot to think about. 

While clothes are powerful, beauty can take things to another level. Check out our guide to revenge makeup: the TikTok beauty trend that stunts on your ex.