Ivanka Trump’s Outfits That Missed the Mark

In April 2024, Ivanka Trump shared some personal images of a trip to Utah with her husband, Jared Kushner, on Instagram. One of the photos features her in a white, lace minidress, an Aztec-print jacket, a chunky belt, and worn-in cowboy boots.

While the coastal cowgirl aesthetic has been a trendy spring look for a couple of years now, pulling it off isn’t as easy as it may seem. “The coastal cowgirl aesthetic uses Western-influenced styles but in lightweight fabrics and neutral shades which adds a beachy vibe,” stylist Megan Watkins explained to Metro. “This trend is all about laid-back, carefree fashion – think statement cowboy boots paired with denim cut-offs and plaid shirts.” In Ivanka’s case, the look seems overly forced in hopes of looking trendy, which actually backfired, as she looked anything but carefree. With her perfectly styled hair, makeup, and hoop earrings, Donald Trump’s first daughter ended up looking like she was wearing a costume of the coastal cowgirl aesthetic rather than the real deal.

When Ivanka Trump showed up at The White House in May 2020 for an event focused on supporting the United States’ agriculture community, her outfit stole everyone’s focus. It may have been 2020, but in Trump’s closet, it was clearly still 2010.

Trump, who was a senior advisor at the time, wore a white, sleeveless A-line dress that was definitely outdated, but nobody would have paid that much attention to it had she not over-accessorized it. Not only did she add a scarf around her neck, but she also wore a black statement belt around her waist — a style that epitomizes the millennial business-casual fashion of the early 2010s. While we’re all about embracing the versatility of a classic black belt, this definitely wasn’t the way to do it. A thinner white belt would have looked better here in our opinion.

The first daughter is no stranger to looking fashionable, as plenty of Ivanka Trump’s outfits have had special meanings. However, her looks also don’t always impress, and the pale-yellow dress she wore to the quarterfinals of the Miami Open in March 2024 is a great example of just that.

The fit of the dress seemed a bit off, and when you’re the president’s daughter, perfect tailoring is expected anytime you’re out in public. If that weren’t enough, the dress’ pockets seemed oddly placed, and the length of the sleeves was a tad too short, making it appear as if the dress was a last-minute decision. In fact, the entire way it fit her makes us believe that she simply should have sized up and potentially cinched the waist. But hey, at least the pale-yellow color of the dress suited the mother of three; it just wasn’t enough for us to disregard the tailoring.

In June 2019, President Donald Trump was on a three-day visit to London, England, and as his senior advisor, Ivanka Trump accompanied him. While fashion wasn’t a priority for this trip — they weren’t going to the Met Gala, but Ivanka doesn’t have the best track record there, either — we can’t help but cringe at the polka-dot skirt and blouse that Ivanka wore while there.

While polka dots are one of the classic trends staging a comeback in 2025, the pattern wasn’t that big six years ago, even if some people believe them to be eternal and not limited to ever-shifting style fads. And sadly, Ivanka’s interpretation of the trend was all over the place. Between the tiny pattern of the skirt and the larger polka dots on the blouse, plus the detailing on the sleeves, Ivanka’s take on the vintage trend ended up looking too busy. Your eyes don’t know where to go when you look at it, and that’s not what you want when you’re on a work trip.

In July 2017, Germany hosted the G20 summit, and while plenty of important topics were discussed, all we could focus on was the muted, baby-pink dress Ivanka Trump wore ahead of a plenary session. Now, don’t get us wrong: The knee-length dress with a cinched-in waist isn’t bad at all — and we actually adore the dramatic bows on the sleeves — but the G20 summit didn’t seem like the right occasion for a look this bold.

Had the first daughter worn this coquette dress to a red-carpet event or even an occasion at The White House, it would have been lovely, but bold fashion just doesn’t have a place at a summit like this. We do hope that Trump decides to bring this look back, hopefully at a more appropriate event. This look would be perfect for Easter or any springtime gathering, for example. And while Trump has experimented with a variety of trends over the years, we hope we get to see her dabble into coquette fashion some more, as this dress could be great on her in a different context.

When it comes to the Met Gala, also known as the fashion event of the year, what you wear is all that matters. In May 2016, the theme was “Manus x Machina: Fashion in an Age of Technology,” and while a lot of attendees embraced the futuristic and modern approach to fashion, Ivanka Trump was not one of them. 

The socialite attended the New York City event alongside her husband, Jared Kushner, but it doesn’t seem like Trump cared too much about the night’s dress code. She showed up in a red Ralph Lauren Collection jumpsuit that featured a statement train, and while the look isn’t awful, it certainly didn’t impress at a star-studded event like the Met Gala. We don’t hate the outfit — it would be cute in a more casual setting — but we would have loved to see Trump embrace the theme and show us what she can do.

By now, it’s clear that when it comes to sports events, Ivanka Trump is prone to rather odd fashion choices. In February 2018, the first daughter attended a men’s curling gold medal game at the PyeongChang 2018 Winter Olympics, and her choice of clothing was definitely questionable. 

She showed up to the event in a matching sweater set consisting of a knee-length skirt and a matching long-sleeved top. Sadly, Trump simply didn’t pull the dramatic pattern and asymmetrical cut off. Was she trying to show off her edgier fashion side? Style is all about self-expression, but crossing the line where it ends up looking forced is very easy, as Trump would later know again thanks to her coastal-cowgirl mishap. Besides, she was at a sports event, so wearing a dramatic piece like this one was a little unnecessary. We’d recommend saving something like this for Christmas, a time when borderline-cheesy clothing isn’t questioned.

While Ivanka Trump doesn’t always fail with her fashion choices, she does seem to wear stylish pieces on the wrong occasions. In fact, overdressing seems to be the name of the game when it comes to her style. So, when she was spotted on a casual walk with her family in December 2022 in Miami, Florida, in a white midi dress, we couldn’t help but question her choice of dress.

The vintage cut of it made Trump look older than she was, but that’s something we could ultimately get past. On the other hand, the fact that she is wearing a sophisticated midi while her son is skateboarding in front of her isn’t something we can easily move on from. The first daughter clearly has a problem with dressing for the errands she is doing — and in this case, a more casual ‘fit would have made much more sense. Maybe someone could get her a simple pair of jeans and a tee for her birthday?

In March 2018, Ivanka Trump attended an event at The White House for which she thought it was appropriate to wear a dark-green jumpsuit with a black turtleneck underneath. As soon as we saw the look, we noticed that the combination was peculiar, and we couldn’t help but think that the jumpsuit would have looked a million times better if she’d ditched the turtleneck entirely.

Now, we get it — perhaps she was worried about showing too much cleavage à la Lauren Sánchez in some of her most inappropriate outfits, but that is an easy fix. Simply wear something entirely different. She could have saved the green jumpsuit for an occasion she deemed cleavage-appropriate and worn a different outfit. After all, it’s hard to believe that Trump doesn’t have access to a plethora of different options for every event she attends.

There’s a reason why minimalism in fashion became so popular — it’s much easier to pull off than a busy look. And one of the best examples of that is Ivanka Trump’s dress at the Team USA Awards in April 2018.

When the first daughter showed up on the stage, her Nalani fit-and-flare lace midi dress by Alexis, which retailed for $1,085 at the time, definitely put her in the spotlight. Trump wore the intricate midi-length black-and-white dress, which not only had a lace-like pattern on it but also consisted of a layered skirt and flared sleeves, with black, bedazzled heels. Of course, this ended up looking as chaotic as it sounds. Trump may love a bold pattern and an even bolder silhouette, but this fashion moment certainly doesn’t impress us — and it proves that pulling off both at the same time isn’t easy.

When Ivanka Trump attended a luxury hotel opening in Las Vegas in December 2023, we certainly didn’t expect her outfit to be boring. After all, Sin City is known as a place where one can go for more daring fashion choices, but Trump’s overly long silver sequin skirt dress definitely isn’t the holiday party vibe that we had in mind.

The sequins of the Monique Lhuillier gown definitely resurfaced some painful Y2K fashion memories, but we would have been able to handle those had the first daughter opted for a shorter length. Instead, it literally ended up looking like she had just draped an enormous piece of sequin fabric around her waist and called it a day, especially because the fabric awkwardly gathered at her feet. And we do understand that the designer most likely intended it to look this way, but in that case, Trump didn’t own the look like it was intended to be worn. If she’d stood with more confidence, it would’ve looked more intentional.

As a White House senior advisor, Ivanka Trump attended numerous events during father Donald Trump’s first presidential term, and while her fashion choices were appropriate most of the time, calling them fashionable would be inaccurate. Just one example of that would be the attire she wore at the annual meeting of the President’s Interagency Task Force in October 2018.

She showed up in an all-white look, which is an odd choice considering the meeting was held in the fall. However, we could have forgiven her for breaking the rule of not wearing white after Labor Day — maybe even applauded her because fashion rules like that always seem a little ridiculous — had Trump not decided to spice up the skirt and blouse set with an off-white chunky belt. Someone truly needs to go through Ivanka’s belt collection and encourage her to part ways with most of them. A belt around your waist certainly has a place and time, but this wasn’t it. “A thicker belt is great when you want more of a corset type of vibe or when you want extra waist definition,” stylist Samantha Dawn explained to Good Morning America. The issue is that Trump’s outfit already had a defined waist, making the belt completely unnecessary and out of place.

Perhaps the most shocking part about Ivanka Trump’s fashion mishaps over the years is that even though she grew up in the spotlight as a socialite thanks to her famous father, she has seemingly never mastered the art of wearing clothing that photographs well. So, when Trump showed up at the White House Summit on Human Trafficking: The 20th Anniversary of the Trafficking Victims Protection Act of 2000 event in January 2020, nobody was surprised that her dress looked like a bathrobe. 

Granted, we don’t know if this is the vibe it evoked in person (even though it’s hard to imagine it wouldn’t), but in photos, the dress looks like she was headed to the spa, not an important meeting. It’s a shame, really. This garment could’ve been worn in a really elevated way.

As we’ve already established, Ivanka Trump’s looks could often pass as fashionable were it not for the bold and busy patterns she continuously reaches for. We love a good pattern, but pulling one off isn’t as easy as it sounds — and the first daughter certainly struggles with it.

In August 2020, she attended an event in the Eisenhower Executive Office Building in Washington, D.C., and her look brought to mind grandma’s curtains. The cut of the dress combined with the pattern and the chunky waist detailing all contributed to the end result: a dress that should have never seen the light of day on Trump. But hey, at least her hair and makeup were perfect, which isn’t always the case. If you’re curious, check out Ivanka Trump’s biggest makeup mistakes to see just how relatable the first daughter can actually be. After all, we’ve all had our fair share of both fashion that didn’t impress and makeup that was awful. Luckily for us, none of it happened in the spotlight. Now, check out the Trump family’s worst looks of 2024 for more fashion critiques.