Tiffany Trump Has Worn Some Seriously Out-Of-Date Outfits

The art of maintaining fashion-forward looks amid the many crazes that rock the design world is just that: an art — one many can't manage when the enticing gaze of a well-followed trend captures their eye. The result? Horribly out-of-date or mismatched looks. Celebrities are no different and Tiffany Trump is the perfect example. President Donald Trump's youngest daughter's presence in the public eye is nothing new, and neither are her outdated outfits.

Tiffany's shown off her lethal legs more than once and her hair transformation can't go unnoticed, yet her outfit choices are not always on point. Despite her fame and status, it's difficult to understand why she continues to wear outfits that don't adequately reflect her age, current trends, or even plain old fashion staples. Given the immense wealth she was born into — with the opportunity to not only shop at but partner with almost any designer label — Tiffany's consistent inability to dress fashionably comes as a shock given her countless resources. With that last name, Tiffany could afford a curated closet. However, she's proven time and time again that less-than-stylish outfits are the true staples in her wardrobe. Let's take a look at Tiffany's most outdated outfits.

Following her father's second inauguration in January 2025, Tiffany Trump stepped out in this red wine and black look. The cape coat, unfortunately, lacks any modern vision. It's a tired piece that's only defining detail is a 2016-style tie belt. While the color is gorgeous, it's an odd choice for a daytime event where lighter, brighter colors are often preferred over such somber hues. Similarly, her dated opera gloves are too dark (and too long), as the leather material does nothing to help modernize their vibe. In turn, not only does the outfit look old, but it makes Tiffany look older, too.

Tiffany Trump's baby blue set for the 2020 State of the Union was an unexpected double shoutout to the peplum craze of the early 2010s, as both her top and skirt featured the wavy material. The trend fell out of fashion's favor and has struggled to return since, which makes Tiffany's choice to wear a buttoned top with the flared, pleated effect scream a lack of fashion-forward thinking. But the out-of-date cut matches the dated, chunky buttons of the '60s mod fashion. The skinny belt could have worked, perhaps, had she not placed it so high on her waist that it cut both the outfit and her all wrong.

This outfit, shared in the days leading up to Tiffany Trump's father's 2025 inauguration, is a frumpy twist on the long coat, tall boot staple. Tiffany's coat — with its high neckline, stiff collar, and puffed shoulders — reads pilgrim. Tiffany embraced the tie belt once again, proving the outdated 2010s style has a seemingly permanent place in her repertoire. And of course, the huge white buttons bring to mind the clip-on earring fad of the late '50s and early '60s. The jacket is simply blah, to be honest, as the color washes out Tiffany's skin and hair. Her awkward leather kitten heel boots and caked, smoky eye makeup don't do her any favors, either.

Tiffany Trump sported this look back in October 2024. This outfit as a whole — the tailored black slacks, the chiffon top, and the Oscar De La Renta tweed jacket — has been a go-to for the MAGA set for years. At this point, however, it's tired! The chiffon, white button-up is a stark fabric contrast to the heavy and unfinished look of the blazer and the black slacks lack the same volume that the top half of this outfit creates. Together, the outfit is not only out of date, but it also tells of Tiffany's loose grasp on her own personal style.

Worn as part of Tiffany Trump's wedding celebration in 2022, this white lace dress screams dead '80s fashion. The fitted pencil skirt cut with large, puffed shoulders is reminiscent of the styles popularized during the "Dynasty" era. The stiff shoulders are anything but flattering and lack the softness of similar modern sleeves. The pattern of the lace is extremely busy, much like a grandmother's table doily. Combining these two elements makes for a dated look. All around, this outfit choice is extremely outdated and a flashback to forgotten style trends that should stay in the past.

Tiffany Trump might've been photographed in this look for New York Fashion Week in 2017, but this dated outfit looks like something she stole from the back of big sister Ivanka's closet. Reminiscent of the early 2000s, Tiffany's whole outfit reminds us of Snooki's vibe circa "The Jersey Shore." The heavy eye makeup, the choker necklace, the cutouts in the sleeves and on the hem of the skirt, accessorized with shimmering pumps, scream 2000s forgotten fads, and is totally too amateur for a Fashion Week event. 

Tiffany Trump's second look for 2017 New York Fashion Week was a gorgeous step in the right direction, but failed in execution. The colors are incredible, and work well together, but they wash Tiffany out. The dress fails in its cut, as well. The dress attempts to reflect a retro style, but misses the mark, leaving Tiffany looking dated in an outfit that doesn't complement her figure. Styled with a gray heel, which does nothing for the dress, the outfit is a capsule of out-of-date mistakes.