Kimberly Guilfoyle's Biggest Fashion Fails Of 2025

Kimberly Guilfoyle had quite an interesting. She landed her big, fat Greek ambassadorship, making the move to Athens as the new U.S. ambassador to the Mediterranean country. And she moved on from her breakup with former fiancé Donald Trump Jr. Evidently, she's been in a transitional period of her life. For many of us, times like these inspire a transformation: a fresh new bob, the bangs we've been considering for ages, or a new twist on our typical wardrobe. This was not, however, the case for our girl Kimberly. Apparently, her exciting new job, single girl era, and move across the globe were not enough to make Guilfoyle abandon her signature style. Guilfoyle seemingly had a great 2025 on all other fronts, but as usual, it was a bad year for her fashion.

Lots of sparkles, super short hemlines, and a plethora of pink ruled Guilfoyle's fashion choices this year. She stuck with her heavy makeup (and even heavier hair extensions), as well as her love of anything short and tight. Yet, 2025 brought some new additions to her wardrobe, too. She seemed to enjoy sequins more than ever and developed an unusual fascination with one particularly stuffy style of top. Still, to give Guilfoyle credit where credit is due: she might not have an eye for fashion, but she knows what she likes and nothing can change her mind. Let's take a look at Guilfoyle's worst looks of 2025, which are arguably just as Guilfoyle-y as ever.

In November, Kimberly Guilfoyle was tagged in an Instagram photo that showed off what had to be one of her worst looks of the year. Guilfoyle posed in a cream-colored, sparkly gown. From the hips to the floor-length hemline, the dress featured ruffles that extended all the way around the skirt. Between the ruffles and the sequins, this dress felt like something designed by an enthusiastic kindergartner to be worn by a Barbie. Guilfoyle managed to make the look even busier with the biggest, glitziest cross necklace she could get her hands on. (Even Karoline Leavitt's flashy cross necklace pales in comparison.)

If Kimberly Guilfoyle had pursued a career in medicine, we know she would've worn a stethoscope exactly like this. In October, Guilfoyle attended a going away party before jetting off to her new life in Greece. For the occasion, she wore a black dress with a cutout that had a bizarre chain with massive crystal brooch details. Since the event was for Guilfoyle, her goal was probably to get all eyes on her and this 'fit likely achieved that. Unfortunately, it was just plain tacky.

Kimberly Guilfoyle was caught red-handed at the 2025 AmfAR Gala in Cannes in a dress that made even some of her worst outfits from years past look good. Between the mesh neckline, the asymmetry, the vine-inspired lace, and the single big, puffy sleeve, this dress was completely overwhelmed with details, making it look overpowering and way too dramatic. Paired with the bold color and Guilfoyle's unwavering refusal to ditch her heavy, boring extension-centric hairstyle, this whole look was a total mess.

Kimberly Guilfoyle managed to wear another lackluster red dress this year. At the Hellenic Initiative's 9th Annual Gala, she looked like she made a fiery attempt at turning Grandma's crafts into glam. The oddly-textured fabric over the shorter lining made it look like she threw a net on over a club-ready minidress. Styled with her heavy, waist-length hair, intense eye makeup, and tiny red bag, nothing about this look worked.

With her wardrobe's reputation, it isn't easy for Kimberly Guilfoyle to shock us with an outfit. And yet, this Mother's Day look made us do a double-take. Guilfoyle posed with her son, Ronan, wearing a super-short pink minidress with buttons down the front and a white Peter Pan collar. Between the length and the childish vibes, this dress was totally inappropriate. With her hair styled especially straight and platform sandals, she looked a bit like a doll brought to life — and not in a good way.

If there's one day of the year when it's entirely acceptable to wear your sparkliest, most attention-grabbing outfit, it has to be your birthday. So Kimberly Guilfoyle shouldn't be entirely blamed for the gold minidress she sported for her b-day this year. Yet, we can blame Guilfoyle for — as usual — refusing to ditch her beloved tight, fast fashion-esque minidresses for something a bit less tacky and overdone. But we suppose it's also on-brand to look like New Year's Eve decor when you are kicking off your new year, so to speak.

Kimberly Guilfoyle was oddly committed to feeling pretty in pink this year. Yet, the pink looks she chose just went from bad to worse. In April, Guilfoyle was tagged in a photo on Instagram that showed her wearing a bubblegum pink minidress. The dress had a sequined mock neck, as well as sequined cuffs. Short of a costume party, we can't imagine what event would make this dress look appropriate. But, paired with an overload of hair and makeup, it somehow got even worse.

In June, Kimberly Guilfoyle showed off one of her most dramatic outfits of the year. And, of course, it was in her favorite color of the year: monochromatic pink. She wore a satin-y pink dress with a big, fluffy pink coat and a matching bedazzled pink bag. This outfit definitely only works if you want all eyes on you. And to make matters worse, based on her Instagram caption, it seems like she wore this over-the-top ensemble to someone's wedding. Yikes.

Evidently, Kimberly Guilfoyle didn't make as many changes to her wardrobe in 2025 as she maybe should have. Yet, she did put a lot of new focus on one particular style of top that gave us pause.

Time and time again, Guilfoyle sported pussy-bow tops in various colors. It was almost as if she found one single style of office-appropriate clothing and ran with it. Sure, it's better than wearing a body-con minidress to a work meeting — but it still reminded us of George Washington every time.