Trump Family Looks That Meant More Than You Realized

Members of the Trump family have made many outdated style choices over the years, but none of the Trumps are as firmly entrenched in the past as their patriarch. Donald Trump is also arguably his family's dullest dresser; however, his C-suite suits from a bygone era might be just as meaningful as some of Melania Trump's headline-snagging outfits. 

If Gordon Gekko got so greedy that he stiffed his tailor, you might get a Trump suit: an ill-fitting '80s throwback that doesn't signal an interest in progress or innovation. His dumpy, regressive attire has been endlessly analyzed, and it's believed that he continued wearing his long-favored baggy suits from the Italian label Brioni when he decided to pursue a political career even though he was trumpeting his "America first" message at rallies. On why Donald favors such a spacious silhouette, Jatin Vengurlekar, the creative director for Sydney's Montagio Custom Tailoring, told The Sydney Morning Herald, "It looks as if Trump is trying [to] achieve an all-imposing look. The bigger the suit, the less you can ignore."

When Trump wears one of his frumpy jackets, his vanity is sometimes exposed. Tell-tale lumps reveal the presence of shoulder pads (as seen above), an artifice that further bolsters his bulk while creating the illusion of a slimmer waistline. The cherry on top is the red MAGA hat, which makes his look like business on bottom, and average Joe up top. A fake Time magazine cover posted on the official White House Instagram account made it blatantly obvious that Donald would like to replace that cap with a gold crown, as he was depicted wearing one. And monarchical references seem to be a through-line in many of the Trumps' most meaningful outfits. Here are some more looks worth noting.

Melania Trump wore a striking diamond brooch to go inaugural ball-hopping in 2025. According to the Daily Mail, the piece, which she wore affixed to her black choker, was a loan designed by Harry Winston, who once dreamed of making a collection of jewelry for American first ladies akin to the British monarchy's famed treasure hoard.

In addition to possibly daydreaming about crown jewels while planning her look for three inaugural balls, Melania might have been thinking about her husband's plan to immediately start scribbling his name on executive orders after his inauguration. Some social media users observed that the black ribbon on her white Hervé Pierre gown bore a striking resemblance to Donald Trump's angular signature, which he scrawls in Sharpie. Recalling the design's conception, Pierre told Hello!, "[Melania] made this kind of zig-zag, up-in-the-air [gesture] to explain something sharp she had in mind." It does sound like Melania was mimicking how her husband signs his John Hancock, albeit subconsciously. 

According to Pierre, the bold accent on the column gown was also simply Melania's preferred sartorial aesthetic. "She likes tailored suits and sharp lines," he revealed.

For many, Ivanka Trump's 2025 inauguration outfit was giving off major under-his-eye vibes. Her emerald green Dior ensemble included a pencil skirt and jacket with a scarf-like detail. A skinny belt was tightly lashed around her waist, creating a somewhat severe silhouette. Internet users found the look disturbingly similar to the Gilead garb worn by the villainous Serena Waterford on "The Handmaid's Tale," which imagines a patriarchal future where women's rights and bodily autonomy are stripped away. Not a good look when your father's administration is being decried for its attacks on reproductive freedom.

But to fashion expert Lauren Rothman, Trump's outfit looked like something that might be found in Catherine, Princess of Wales' closet. The Brit does wear a lot of monochromatic ensembles, and Ivanka finished her look with a headpiece reminiscent of a royal's fascinator: a beret-like hat worn at a jaunty angle. Ivanka even carried a Lady Dior handbag, which got its name from Princess Diana. "Her look is really a signal that indicates her strong understanding of the political kingdom," Rothman told BBC. However, Ivanka didn't join her father's administration in 2025, so perhaps now she simply views herself as part of an elite dynastic class — one that uses clothing to convey power and prestige.

Donald Trump Jr. reportedly criticized Kimberly Guilfoyle's style before ditching her for glamorous socialite Bettina Anderson, but his taste in fashion might be even more unsavory. In 2019, he took to Instagram to share photos from an outdoorsy date with his now-ex. Surprisingly, none of Guilfoyle's plentiful inappropriate outfits made an appearance. However, Donald Jr. had on an army green T-shirt emblazoned with the skull symbol worn by the Marvel vigilante The Punisher. It became controversial when it was adopted by white nationalists and other hate groups. The version on Donald Jr.'s shirt had Donald Trump's hair.

On the skull's forehead, there was a circle of stars around the Roman numeral III. This is the logo of the Three Percenters, an anti-government militia group that has been connected to terrorist activity. Some of its members also participated in the January 6 U.S. Capitol attack. Trump's feelings about the rioters became abundantly clear when he pardoned them all, and in a 2024 tweet about the insurrection, Donald Jr. shared an anti-government message: "I do hope that it was the start of something real though, where people realize that their government is not what they thought it to be unite to take back their country!!!"

Tiffany Trump's relationship with Donald Trump has never seemed all that close, so it wasn't exactly a shocker when she didn't go traipsing around the country with him in a MAGA hat during his presidential campaigns. However, it did raise a few eyebrows when she shunned Republican red for white when choosing an outfit for his 2019 State of the Union address. Ahead of the event, the House Democratic Women's Working Group asked congresswomen to wear white to pay tribute to the women's suffragette movement. "We'll honor all those who came before us & send a message of solidarity that we're not going back on our hard-earned rights!" tweeted the group's leader, Rep. Lois Frankel. A large number of Congressional Democrats obliged, and some social media users construed Trump's daughter's clothing as support for his opposition. 

Donald Trump Jr.'s then-girlfriend, Kimberly Guilfoyle, also wore white, while Ivanka Trump, Melania Trump, and Lara Trump all sartorially snubbed the Dems by sporting dark colors. Ahead of the 2024 election, Tiffany did tweet, "My father will NOT sign a national abortion ban," so apparently, she does care about women retaining their rights (to a certain extent, anyway).

For the 2017 Liberty Ball, Lara Trump wore a yellow gown with an open back and heavy embellishments on the bodice, skirt, and sleeves. It was the work of "Under the Gunn" alum Oscar Garcia-Lopez, whose story of how he came to the United States is one Donald Trump is working to eradicate. In a Telemundo 51 interview, the designer admitted to entering the country as an undocumented immigrant. "I crossed the border, kind of like in the Indiana Jones movies," he said (via Cibercuba).

While she probably didn't view her decision this way, Lara demonstrated the potential immigrants could offer America by showing off Garcia-Lopez's work again at the 2025 Liberty Ball. Lara accessorized his creation — a MAGA-red dress with detached sleeves and a ruffle on the back — with an ostentatious ruby necklace that the Daily Mail likened to one worn by Queen Camilla. Although the red gown had little in common visually with Lara's 2017 ensemble, she explained her design choices by telling the New York Post, "I wanted to mimic the same things that happened [in 2017], because it was a really, really incredible time then and we're hoping for the same now." She added that she now prefers to stick to a "patriotic" color palette. 

For the 2025 Liberty Ball, Ivanka Trump wore a white gown with black floral embroidery that was instantly recognizable to any fan of the 1954 Audrey Hepburn movie "Sabrina." Hepburn plays the daughter of a chauffeur in the romantic dramedy, but Ivanka's replica of the film's iconic Givenchy dress was not a hat tip to the working class. "Audrey Hepburn has long been a personal inspiration to Ivanka," a rep for Ivanka told Page Six. "She views it as a great privilege to honor her legacy in this way and is incredibly grateful to the team at Givenchy for bringing this moment to life."

Ivanka's admiration for Hepburn may be somewhat superficial in nature. Hepburn's son, Sean Hepburn Ferrer, told the Daily Mail the Trumps' values don't align with those his mother held dear. "[She] fought on behalf of the disenfranchised children worldwide regardless of the ideological environment in which they were born in," he explained.

As for the shoutout to Givenchy in the statement about the dress, its message was loud and clear; it served as a reminder that some major fashion houses had warmed to the idea of working with the Trumps after the family was shunned by so many designers during Donald Trump's first term.

Alongside Ivanka Trump, Melania Trump adopted the British royals' practice of sporting headwear to important events for Donald Trump's 2025 inauguration. However, the severe lines of her navy coat and matching boater hat landed her on the list of the inauguration's worst-dressed stars. To some social media users, she looked like a darker version of Carmen Sandiego — and perhaps Trump will send Melania Montreal on clandestine scouting missions for potential Trump property locations in Canada as he plots to annex the country as America's 51st state.

Some experts said that Melania's dark, somber outfit and harsh silhouette were meant to serve as a type of sartorial armor or convey that she was not in the mood to celebrate. "She was almost removing herself from the event in some ways," Parsons School of Design professor Hazel Clark told Sky News. There were also jokes aplenty about how Melania's wide hat brim made it difficult for Donald Trump to kiss her. However, according to the piece's designer, Eric Javits, the hat wasn't meant to put distance between Melania and her husband; it represented America distancing itself from progressive views. "It's a time of some restraint, and it's really sort of a turning point to more conservative values, I think," Javits told ABC News. As for the overall vibe of Melania's outfit, The New York Times chief fashion critic, Vanessa Friedman, suggested it was an illustration of Donald Trump's imperialistic appetites.

Much ado has been made about Donald Trump taping his ties and wearing them far too long. In his book "Let Me Finish," former New Jersey governor Chris Christie claims that Trump once divulged why his tacky ties are so long: "It makes you look thinner." As for why Trump seems to prefer red ties, menswear expert Derek Guy suggested it's unrelated to party loyalty. "Trump dresses as a flashy businessman and entertainer. ... His bright red tie is a matter of branding," he tweeted.

But Trump took a break from promoting his brand at his 2025 inauguration. His tie was a blend of blue, red, and the color they make when mixed together: purple. On the "Welcome to MAGAland: Trump's Second 100 Days" podcast, journalist Kelly Laco suggested the mixing of the colors of America's two major political parties indicated that Trump was portraying himself as a unifier, despite his seething disdain for the Democratic Party. "He wants to bring in Republicans and Democrats, as he's already done in his cabinet with RFK Jr. and Tulsi Gabbard," she said.

Lara Trump has used violent rhetoric when talking about the United States' southern border. In a 2021 "Justice with Judge Jeanine" interview (via Acyn on X), she said of American citizens living there, "I guess they better arm up and get guns and be ready, and maybe they're going to have start taking matters into their own hands."

Trump wasn't armed up when she visited the border with deputy presidential special envoy to the Middle East Morgan Ortagus and Attorney General Pam Bondi in 2024. However, the former RNC co-chair was dressed like she was prepared to use a weapon. Because the print on her camouflage shirt is associated with the military, she sent an incendiary, inhumane message with her garb — whether intentional or not — that echoed her aforementioned words: that she viewed people trying to cross the border as enemies to take down.

In response to pictures Trump shared on X, numerous critics also accused her of making the trip to the border wall for a photo op. "Border Patrol Barbie? This is ridiculous," one person tweeted. Even Republicans cringed when they saw the photos. "We're weeks out from the election & you're cosplaying in camo for a photo shoot at the border? Lmfao we're such an unserious party," another post read.

There was nothing remarkable about the appearance of the suit Barron Trump wore for Donald Trump's second inauguration. However, the story behind it closely connects the first son to some controversial figures. Barron's tailor, Nathan Pearce, told Women's Wear Daily that Barron was referred to him by entrepreneur Justin Waller, a popular manosphere personality who once got booted from YouTube for promoting Andrew Tate's The Real World business school. Of how he met Barron, Waller told the Daily Mail, "[Barron's friend Bo Loudon] reached out to me and told me that Barron watches my content and would like to invite me to dinner at Mar-a-Lago."

Tate is also pals with Barron. "I'm very close to the Trump family. I know them well. I spoke to Barron after the incident [In Butler]," he told reporters in February 2025 (via Republicans against Trump on X). Tate is a self-described misogynist who has been charged with several crimes, including human trafficking and rape. The influencer has said women deserve some blame for their sexual assaults, and when describing the business that Waller helped him with, he said the objective was to "inspire a girl to make money and give you the money," per Dissent. Knowing its dark ties certainly puts Barron's dark blue suit in a different light.

Ivanka Trump had a close relationship with her mother, Ivana Trump. When she was still in elementary school, Ivanka began attending fashion shows with her glamorous mom, and Ivana later supported her daughter's career as a clothing designer. In a 2018 Page Six interview, Ivana even said she wanted to see Ivanka exit her father's administration and go back to working in fashion. 

Sadly, Ivana died in 2022 without seeing her wish come to fruition. However, it became evident that Ivanka still viewed fashion as a tie to her mother the following year when she attended a party with a 1920s theme. She sported a white Bob Mackie minidress covered in white fringe, which gave it a flapper vibe. She inherited the garment from Ivana, who had worn it to Studio 54's 25th anniversary party.

The first daughter has always been fond of her mom's Bob Mackie pieces. In 2014, she modeled a similar white, gold, and black ombré dress for her social media followers. Apparently, she borrowed it without her mom's permission. "Last night in my mother's vintage Bob Mackie dress," she wrote in a since-deleted post (via E! News). "It's a good thing she's not on Instagram."

When Ukrainian President Volodymyr Zelenskyy sat down with Donald Trump in the Oval Office in February 2025, the American president was reportedly unhappy that his guest had dressed like a man whose country was at war and not a contestant on "The Apprentice." Sources told Axios the White House had advised Zelenskyy to wear a suit to the contentious meeting, but he ignored the request.

Days later, Melania Trump made a rare Capitol Hill appearance to attend her own meeting about the Take It Down Act. She wore a tan Ralph Lauren pantsuit, and there was speculation that her outfit was a pointed response to the furor over Zelenskyy not getting suited and booted. "Melania wore that suit because Zelensky couldn't be bothered to wear one ... right?" tweeted one netizen. For some, the look also brought to mind the feverish outcry over Barack Obama's famous tan suit.

Another possibility is that Melania was trying to channel a royal, as Kate Middleton has also stepped out in a tan pantsuit. Or perhaps she was hoping to annoy her husband the same way Zelenskyy purportedly did. In her book "Free, Melania: The Unauthorized Biography," journalist Kate Bennett writes, "I have a theory that when the Trumps are unhappy with each other, Melania wears menswear —because Trump notoriously likes to see women in tight, short, ubersexy and feminine dresses." Unfortunately, unless Melania decides to give us an outfit explainer, we'll never know if she was really trying to stick it to her man by doing menswear in tan.