Ivanka Trump Outfits That Just Weren't Flattering

Ivanka Trump bid a sad farewell to her clothing brand in 2018, but perhaps it was for the best. While she never traipsed around advertising her apathy on her outerwear like Melania Trump did with her controversial "I really don't care" jacket, there is ample evidence that fashion isn't always Ivanka's forte. 

In an appearance on the "Lex Fridman Podcast," Ivanka revealed what she takes into consideration when choosing an outfit: "I want to be comfortable, and that helps me be confident and in command." Nevertheless, she didn't exactly exude comfort in the forest green Dior coat she wore to Donald Trump's second inauguration. For many, her look brought to mind Serena Joy, the villainous but oppressed wife of Commander Waterford in "The Handmaid's Tale." Unfortunately for Ivanka, adding a sassy beret to her inauguration outfit wasn't enough to spare her from comparisons to the character.

This unfortunate style misstep reminded some onlookers of a society in which women are second-class citizens, all while she was repping an administration under fire for doing to women's rights what her Dior ensemble was doing to her midsection: whittling them away. Nevertheless, this look has been trumped by even more unflattering ensembles.

In the movie "The Sweetest Thing," there's a montage of Christina Applegate and Cameron Diaz trying on various pop culture-themed outfits in a dressing room. Ivanka Trump was likely unaware of this scene when she got dressed for the comedy's 2002 premiere in New York City, but she somehow she managed to look like she had scooped up a bunch of random items of clothing from that shopping sesh and put them on. Her chaotic look included a heavy denim jacket with the cuffs rolled up and a black top tucked into an asymmetrical skirt that couldn't decide whether it wanted to be a fluttery negligee or a clingy lace chemise. On her feet, she wore pointy-toed heels with Xs marking the spot where they broke up the long lines of her bronzed legs (which were significantly tanner than her face).

Making herself appear even more weighed down from the waist up, Trump tossed on a wide scarf — not one of the skinny scarves that were so trendy at the time. The jean jacket and scarf combo had the unfortunate effect of making Trump's torso look boxy. If that was the silhouette she was going for, she would have been better off covering it all up with that giant book Diaz holds in the movie poster.

On the "Lex Fridman Podcast," Ivanka Trump recalled how Anna Wintour called her personally to offer her a position at Vogue in 2004. However, in this alternate version of "The Devil Wears Prada," Trump had just graduated from business school, and she turned down the venerable VIP of the fashion industry because she wanted to work with her father in real estate. "I never thought I would go into fashion," Trump said. That became quite clear when she wore the outfit above to designer Behnaz Sarafpour's New York Fashion Week show in 2002. It's rather miraculous that Wintour gave her a ring after Trump decided that a denim miniskirt with a frayed hem was appropriate for NYFW. The stiff fabric jutted away from her body, creating a box around her hips that made them appear wider.

When describing how she packs her suitcase, Trump once told GQ, "I'm very meticulous in the way I do things, so I use layers of tissue paper." Maybe what happened here is that a piece of tattered packing tissue got stuck to her top? The diagonal cut of the raw hem drew further attention to her hip area (and not in a good way). The top's filmy fabric also wasn't lying flat, creating unflattering folds that made her look lumpy around the midsection. It's just too easy to imagine Wintour channeling Miranda Priestly by snidely asking Trump if she "fished it out of some clearance bin." Perhaps Trump's Met Gala snub signifies that the Vogue editor-in-chief no longer views the heiress as being sartorially relevant.

By the time Ivanka Trump wore a tie-dye dress in 2003, she'd already been spotted in some truly wild runway looks as part of her modeling career; however, this look was one of her own choosing. Her tie-dye garment with bell sleeves is actually not a swimsuit coverup that she found at a seaside souvenir shop but an off-the-shoulder shift dress designed by Behnaz Sarafpour. Sadly, Ivanka wasn't heading to a beach bonfire to toss it in the flames. Instead, she wore this to a Vogue party attended by fashion's elite, including Vera Wang, Zac Posen, and, of course, Anna Wintour.

It's nearly impossible to make a splattered dress look like anything other than the result of gastronomical distress. The giant bodily fluid bullseye on Trump's torso featured a bile-colored splotch and rings in a watered-down brown shade that clashed with the golden tones of her tan. Because the dress's sleeves covered her hands and extended all the way down to the hem, her arms appeared unnaturally long. Trump's garment really deserved to meet a fiery fate, so hopefully she was carrying a lighter in that cigar box purse — which, by the way, didn't complement the beachy vibe or fluorescent color scheme of her dress.

Purple pain, purple pain. Before Ivanka Trump played the role of jelly in this socialite sandwich, it seems she also got the memo to wear taffeta to the Young Friends After Party at Frederick's. But whereas Ivanka's companions look dressed for prom circa 2005 — the time of the event — she looks ready to toss off her eyesore of a coat and school Charlie Murphy in a game of basketball. Then again, when Dave Chappelle wore a knockoff of one of Prince's most iconic purple ensembles in his famous "Chappelle's Show" sketch, the comic looked far more fashionable than Ivanka does in her stiff, toe-skimming overcoat.

Although Donald Trump used Prince's music without his estate's permission during his 2020 campaign, there's no way he procured this outré outerwear for Ivanka by pilfering it from Prince's closet — it's far too tacky to have ever belonged to the Purple One. The coat's straight cut transformed it into a rigid column with a bust of Ivanka's head resting on top. In addition to making her body shapeless and washing her out thanks to the color, the coat was possibly making her too warm — the party took place in May. Ivanka's companions were wearing far more seasonally appropriate attire.

When Ivanka Trump appeared on the cover of the now-defunct lad mag Stuff in 2006, she wore a dress with a low-cut bustier bodice designed to create cleavage worthy of a Victoria's Secret catalogue; however, at an event celebrating her sexy Stuff cover, she wore a decidedly unsexy dress — albeit one that referenced the boudoir in a bizarre way.

Her cream shift dress featured a chiffon overlay and a folded neckline that looked a lot like the corner of a bedsheet. Keeping with the bedding theme, the fabric layers swallowed up her torso and fashioned her entire upper body into the shape of a pillow. She finished off the look with bland beige pumps, which were appropriately snooze-worthy and a poor color match for her bronze skin — they looked as if they were white shoes stained by self-tanner.

In her interview with Stuff (via People), Ivanka Trump promised, "You're not going to find me dancing on top of tables or see me trashed outside of Bungalow 8." Perhaps not, but for her 25th birthday celebration in 2006, she did make an outfit choice fit for tabletop dancing. Shimmery horizontal stripes created the illusion of a wider frame from her neck to her upper thigh, and stark black boots cut across her calves, making her legs appear shorter. Together, these unfortunate style choices seemed to significantly diminish her height. This also wasn't a look you'd expect to see on the Trump Organization's vice president of real-estate development. 

Acceptable comparisons include an extra from "Austin Powers in Goldmember" or a pollinator that was ready to party. Yes, the stripes on Trump's shapeless minidress weren't the right alternating colors, but because her headband and boots were black like a bee's antennae, compound eyes, and legs, she looked like a special species of the insect — one that collects pollen from the gilded floral accents inside her father's Trump Tower penthouse. She was even dragging a striped fur coat on the ground that had a similar fuzzy texture to a bee's chitinous hairs. However, at least one person liked the look; People reported that she was spotted kissing "Spider-Man 3" star Topher Grace.

Ivanka Trump might be her father's real estate scion, but she reminded everyone that she was very much Ivana Trump's daughter at Dennis Basso's Fall 2012 Mercedes-Benz Fashion Week show. Basso is a famed furrier who was such good friends with Ivanka's mother that he penned an essay about her for Time immediately following Ivana's heartbreaking death in 2022. "She loved beautiful jewels, clothes, and furs," he recalled. 

Ivanka appeared to be wearing one of Basso's designs when she showed up to support him at NYFW, but if this was the case, it wasn't the best walking advertisement for his wares: a girthy fur vest that resembled a fuzzy life preserver. The passé piece was distractingly bulky, ruining the clean lines of her creased flared trousers and making her look unnaturally top-heavy and slightly uncomfortable.

In 2016, MSNBC's Mika Brzezinski told Town & Country, "You hear that name, Ivanka, and you expect fur, leather, but she's really poised, elegant, down to earth." It seems the "Morning Joe" co-host, who stirred up controversy by meeting with Donald Trump in 2024, has forgotten about this older look, as well as Ivanka's own clothing label, which drew criticism from PETA for the use of rabbit fur.

Ivanka Trump needed to be strong in 2018, as that was when she shut down her eponymous clothing company, and she outwardly portrayed that strength by channeling Popeye. Mere days after the news broke that she was exiting the fashion industry, she was photographed strolling across the White House lawn in a gingham top with balloon sleeves that gave her cartoonishly large forearms like those of the spinach-slurping sailor. Unfortunately, she gave in to some of her worst attiring urges as soon as she was no longer the face of a fashion label and also created comically off-balance proportions by pairing her bulgy blouse with the clothing item at the center of a millennial vs. Gen Z battle: skinny jeans. The top's Victorian vibes checked out with how she described her style to Romy & the Bunnies, but her outdated jeans — not so much. "My style is classic with a modern twist," she said. But as you can see, there's no such twist in this particular outfit.

When Ivanka shut down her fashion company in the wake of boycotts and accusations that she was using her political connections to her advantage, she told Page Six, "I do not know when or if I will ever return to the business, but I do know that my focus for the foreseeable future will be the work I am doing here in Washington, so making this decision now is the only fair outcome for my team and partners." Later, Ivanka would also leave her political career behind.

Ivanka Trump wasn't supposed to be the center of attention at the Team USA Awards, but she ensured that all eyes were on her in a flouncy Alexis Nalani dress with way too many design elements: tiers, bold black lace, and trumpet sleeves. She appeared overwhelmed by an avalanche of fabric, especially with her dainty ankles poking out from beneath the mounds of material. When posing for photographs, it looked as if she was buckling under the dress' weight. 

Trump did try to add some bling to her outfit by donning pointy-toed shoes with bedazzled buckles, but the footwear flourish gave the heels — which were from her own shoe line — a Pilgrim vibe. Overall, her attire was too old-fashioned and matronly for her youthful visage. As one of her Instagram followers put it, "Love you but I don't like that old lady dress on you."

Forget tinfoil hats. Years before the Trump administration opened its arms to Robert F. Kennedy Jr., whom Cheryl Hines insists isn't an actual conspiracy theorist, Ivanka Trump arrayed herself in fabric that bore a striking resemblance to the favorite headwear material of those who want to believe that they're living in an episode of "The X-Files." As she posed alongside Jared Kushner in her date-night look — a Carolina Herrera design — her husband cheekily cupped her posterior.

The opulence made the couple seem particularly out of touch at the time Ivanka posted the photo in 2017 because Donald Trump's freshly inked immigration ban was causing turmoil for so many families. "No, her only response to all of this is 'Look at meee! Look how PRETTY I look!' I mean ... REALLY??" read one reaction on X. When the image started making the rounds again months later, another user posted it alongside a photo of migrant children sleeping underneath silver emergency blankets, writing, "Who wore it better?" 

Aesthetically speaking, the biggest issues with the gown were an awkwardly fitting bodice that elongated Ivanka's bust and the metallic material's color. She'd be better served by her father's favorite precious metal, god, as silver's icy hue doesn't complement her warm skin tone.

What if Cruella de Vil fell on hard times and had to shop from the discount rack at TJ Maxx? While visiting the U.K. in 2019, Ivanka Trump answered that question with her ensemble. Ivanka was preparing to meet with the Britain's then-prime minister, Theresa May, and other leaders to discuss business topics when she made the confounding decision to wear a Dalmatian-spotted blouse and skirt.

This was a surprising look, as it came after years of her fashioning herself as an expert on what women should wear to important business meetings and specializing in selling workwear to the masses. "I design things that are consistent with my personal aesthetic: feminine, ladylike and elegant for a professional woman," she once assured The Wall Street Journal.

The semi-sheer outfit was not a disaster of Ivanka's own making, though. It was actually a Burberry design. Still, somehow even the tiny dots looked cheap, as if a bored Donald Trump had scribbled them on with his Sharpie during one of those dull discussions with his advisory team. The silhouette was also off, thanks to how overloaded with style components Ivanka was from the waist up. There was a pussy-bow, sheer sleeves with patterned cuffs, and the bulge of her top's tuck. However, the biggest eyesore was the strange strip of spots across the chest. Because of the angle, it made her bust look lopsided. 

After Ivanka Trump left politics behind, she must've gotten really into "Yellowstone." She looked like a cattle ranch heiress in boots, cowboy hats, concho belts, and coats with colorful Southwestern patterns. Rustic lace dresses also became part of her wardrobe repertoire. However, she'd already expressed a fondness for such garments, telling Redbook in 2012, "There's nothing I have more of in my closet than little white dresses."

Apparently, she needs to keep her closet fully stocked to feed the blue jean beast residing within. While vacationing in Wyoming in 2019, Ivanka wore a strange denim and eyelet lace combo that resembled a prehistoric aquatic creature gobbling down some poor granny's finest tablecloth. On top of being dowdy, outmoded, and a bit monstrous, the frock's belted waist was pulling the heavy denim down — and taking her boobs with it. Roomy roll-tab sleeves and fabric folds on the skirt also created odd, exaggerated proportions. 

Whenever the Manhattanite-turned-Floridian tries to channel her inner country girl, it reminds us of the start of Gwen Stefani's romance with Blake Shelton — when she started shopping at the same places her now-hubby purchases his cowboy boots. If she ever plots a return to fashion, hopefully Ivanka stops attempting a cowboy chic style.