Tiffany Trump's Party-Girl Outfits Look Like They Were Ripped From Kimberly Guilfoyle's Closet

Tiffany Trump has undergone quite the style transformation over the years, and in her case, that's a very good thing. The younger of President Donald Trump's two daughters enjoyed a freewheeling life during her college years; modeling, partying, and traveling in between her studies at the University of Pennsylvania and later Georgetown Law School. Tiffany was a regular at house parties, clubs, and other locales open only to the élite — she and other children of multimillionaires were even known as the "Snap Pack." Back then, Tiffany often sported a wardrobe that flirted with the boundaries of good taste, some of which could hold its own against the most inappropriate outfits Kimberly Guilfoyle has worn. Tiny miniskirts, deep necklines, and towering heels were her go-tos for almost every occasion. 

As the young woman matured, so too did her style, particularly once Tiffany's father entered the political world (as we know, her almost-sister-in-law hasn't quite followed suit). As first daughter, Tiffany appeared at events in more modest coatdresses, pantsuits, and flowing evening gowns. Then, when she married Michael Boulos in November 2022, she chose a stunning princess dress with long sleeves and a square neckline. Even Tiffany's maternity wear (she's expecting a baby boy in May 2025) leans more Duggar than Snooki. Just for the sake of nostalgia, let's take a look back at Tiffany's wilder fashion days.

Tiffany Trump's twenties might best be described as her Blue Lace Era. The color and fabric recurred a number of times and in a number of different variations in her earliest Instagram posts, such as this one from December 2014. For the unidentified event, the future first daughter chose an outfit that perfectly showed off her killer legs, with a sheer lace overlay barely covering the ultra-minidress. The long sleeves prevented this dress from going fully Kimberly Guilfoyle, but the tight cut and short length definitely fit the definition. Tiffany's dramatic eyeliner is also similar to one of the makeup mistakes Guilfoyle is often guilty of making. In all, the ensemble was perfectly fun and flirty for a college girl, but we can't see the accomplished graduate pulling this number out for a Mar-a-Lago lunch anytime soon.

Back in the day, Tiffany Trump liked to bring a little sparkle to her evenings out. On this particular occasion in June 2018, she and her dear friend and fashion designer, Andrew Warren, stepped out in a couple of his personal creations: Blinged out baseball jackets. Tiffany paired her silver, aqua, and pink number with an equally flashy black mini, plus stilettos so tall she was practically walking on tiptoe. The overall effect was more mish-mash than posh. In fact, it was eerily reminiscent of some of Kimberly Guilfoyle's worst pre-Trump outfits, which featured odd combinations of dresses and outerwear. But Tiffany has updated her closet since then, and these days she's more likely to appear in wools, velvets, and satins without the overdone shine. 

Unsurprisingly for a member of the privileged set, Tiffany Trump spent many a summer in the Hamptons among her equally wealthy friends and acquaintances. Among the lavish activities was at least one charity event in 2015: The VH1 Save the Music's Foundation Hamptons Live Benefit, which helped raise money to fund school music programs. In the midst of the entertainment —Jason Derulo was a featured performer — Tiffany posed on the lawn of the expansive Sagaponack private estate. Once again, her choice of dress was blue lace, this time overlaying a sheer illusion dress with no real skirt to speak of (we're guessing she didn't sit down much). 

A couple of followers wagged their fingers at her on Instagram. "It is not appropriate for you Tiffany," one complained. Others pronounced the dress "sexy," "beautiful," and "a fly outfit." It may have been fly, but it has almost certainly flown out of Tiffany's closet since then. In a stunning bit of irony, Kimberly Guilfoyle attended the VH1 party as well, accompanied by date Marc Leder. No one at the time would have guessed that five years later, she would join the Trump inner circle.

Channeling her inner Britney Spears, Tiffany Trump stepped out in Vegas in a glittering gold-and-black tiger-striped number, paired with spike heels and a new 'do with a fringe of bangs. The look got a solid thumbs-down from her Instagram followers, who thought it too reminiscent of "Showgirls," among other unfavorable comparisons. One commenter wrote simply, "Goooooood....grief." We, on the other hand, were reminded of the time when Kimberly Guilfoyle tried wearing an animal print, which was similarly regrettable. While attending a show during Mercedes-Benz Fashion Week 2011, she opted for the dress above, which stood out like a sore thumb among the other more fashion-forward attendees. Since then, the U.S. ambassador to Greece has wisely steered clear of jungle-inspired wear.

It was all fun in the sun for Tiffany Trump right before Independence Day 2015. She and a friend partied poolside at the Beautique Southampton restaurant on the ritzy South Fork in Long Island. For the occasion, the future first daughter turned once again to her favorite blue lace, this time in the form of a bathing suit that amounted to just a handful of fabric (definitely not made for swimming laps). Her Daisy Dukes provided some bottom coverage, but not much. The look drew plenty of attention on Instagram, with most fans surprisingly praising her style. 

One dissenter did, however, wonder what Tiffany's famous father would think of his little girl donning such skimpy attire so publicly, while another had a different argument: "You seem to party a lot...like all the time, by the looks of your photos. Great! Now we know what you'll be doing while WE the taxpayers, and your dad's boss, will be footing the bill." Alas, the Beautique Southampton is now history, and with any luck, so too is Tiffany's barely-there beachwear.  

This pic from a May 2015 event is one that Tiffany Trump might want to erase from her feed before her son is old enough to see it. The future law school grad's glaringly Barbie-pink minidress once again featured a tacky detail favored by Kimberly Guilfoyle: Big, revealing bodice cutouts. That in itself isn't too unusual — she was 21 at the time, after all — but her accessory was eye-rolling. "My favorite party prop is a toy gun," Tiffany wrote, as if honoring her famous family's support of the Second Amendment. But the duck-face pucker, odd grip, and cutesy frock made her look more like a failed "Sopranos" wannabe than a true baddie.