The Worst Outfits In MAGA Land During Trump's First Term

MAGA land. Like any semi-real principality – Santa's Lapland, Atlantis, or the Khia Asylum — it abides by its own stylistic codes and conventions. In fact, style is essential for MAGA to meet its political goals. "If the greater 'Make America Great Again' goal, as stated, is to clear out the Washington establishment, rather than merely change it, I think that applies to image-making, too," said The New York Times' fashion critic Vanessa Friedman.

"As with most things Trump," continued Friedman, "what was there in the first term has been magnified in the second. That goes for style as well as for policy." Indeed, the MAGA aesthetic of Donald Trump's second term has made headlines for being over-the-top. From the yassified, Instagram filter-esque plastic surgery of Kimberly Guilfoyle and others that birthed the term "Mar-a-Lago face" to Kid Rock's star-spangled jumpsuit and Robert F. Kennedy Jr.'s workout jeans, Trump's second term is anything but minimalist. His first term, though, was chiefly characterized by one simple item: the cherry-red "Make America Great Again" hat.

Between the years of Trump's 2016 election campaign and leaving office in early 2021, the rogue headwear went triple-platinum among Trump's supporters. The unmitigated branding success of the MAGA hat in his first term, however, somewhat overshadowed the fact that there had also been some of the most scandalous first lady outfits ever worn. So, it's high time we took a look at the worst fashion faults from Trump and friends' first four years in the White House.

With Donald Trump having worn ties since the '70s, you'd think he'd have proper knot-tying technique down pat. Or at least when over 30 million Americans are watching.

However, at his first inauguration, Trump employed a novel technique to keep both of his tie strands together: tape. Was it necessary? The then-new president's tie looked relatively stable when facing the elements. If necessary, how about a tie clip? Given that the devil is in the details with fashion, the tape made an otherwise passable outfit a total failure. 

It's important to remember the MAGA-sphere extends beyond just the Trump family. It, of course, also includes the political consultants, like Kellyanne Conway, who has many fashion fails she will never live down. Her 2017 inauguration get-up is certainly one of those fails. 

As per NBC, Conway described her outfit as revolutionary garb. However, the $3,600 Gucci statement outfit looked more like a costume for Wes Anderson's take on the Boston Tea Party. "Kellyanne Conway came dressed as the Nutcracker lol," wrote an X user. That says it all.

The first MAGA White House's press secretary, Sean Spicer, was known as much for his poorly tailored suits as for his combative attitude towards the press. Let's take this example from January 2017, when his suit was a size or two too big around the collar. It's all very David Byrne in "Stop Making Sense." 

Given Spicer's job put him behind a podium in front of the world's media, he should've ensured he tailored that jacket. But don't just take our word for it; according to NBC, the then-president also wasn't impressed with Spicer's suiting.

Ivanka Trump is a woman of many titles. From model to real estate agent, she's done a lot. For some time, she was even the head honcho of her own clothing brand. But even with that experience under her belt, Ivanka has worn many unflattering outfits.

Here's one from 2017, when, photographed alongside husband Jared Kushner, Ivanka looked like she raided her kitchen instead of her wardrobe. The metallic shine and bunched fabric of her dress were more reminiscent of aluminum foil than anything high-fashion. Make sure to save some foil for Thanksgiving, Ivanka!

Ironically, at a Philipp Plein fashion show, Tiffany Trump showed off one of her less fashion-forward looks. At the show, a veritable who's who of the 2010s gathered, from Tyga and Kylie Jenner to internet-prison-hottie Jeremy Meeks. However, the 2017 of it all isn't the issue. This is just a timelessly bad outfit.

The Georgetown Law School graduate was wearing black and navy blue. It's been a long-held fashion commandment that black and navy blue aren't to be worn together. Tiffany very much needed to remind herself of the style basics here.

If there's one member of Donald Trump's political posse that couldn't be left off this list, it's Roger Stone. Stone is a serious clothes horse. Between his tailored suits and statement sunglasses, the political strategist has one strong look. However, he doesn't always get it right.

For example, take Stone's outfit from the premiere of his Netflix documentary, "Get Me Roger Stone," which looked a bit "Bugsy Malone," what with the double-breasted pinstripes, tight tie, and pocket square. There's a fine line between a costume and cool; here, Stone crossed that line. 

When it comes to style, cohesion is important. So, when Jared Kushner paired a bulletproof vest with a preppy suit during a visit to meet U.S. service people in Iraq, he had none of it. Needless to say, the internet (and "Saturday Night Live") had a field day. It's no wonder why Kushner can't stand the media.

"I can't even imagine what the uniformed soldiers were thinking when Jared showed up in a sports coat and designer shades," said one user on X. Indeed, we don't know what Kushner was thinking either.

Either Melania Trump doesn't care about the weather or no one told her the forecast because she definitely didn't dress for a hurricane in 2017. When Melania and Donald were setting off for Texas to see the effects of Hurricane Harvey, the first lady was wearing the furthest thing from waterproofs – stilettos.

It's not the most responsible footwear, and one thing's certain: They're showy. At least, too showy for a hurricane that hit Houston, where almost 100 people died, per the National Oceanic and Atmospheric Administration. Read the room, Melania.

In November 2017, Melania Trump either dressed diplomatically or made a culturally inappropriate faux pas — depending on how you see it — at a state dinner in China.

However you view it, her Gucci cheongsam dress, with its bright patterns and fluffy pink armbands, was not one befitting the occasion. For instance, just look at how demurely Peng Liyuan, the wife of China's president, Xi Jinping, was dressed. And yet, Melania's ensemble hasn't even touched our list of 10 tasteless first lady looks that gave worst-dressed a new meaning.

Ivanka Trump wore a maximalist dress to a 2018 event held in honor of medaling U.S. winter Olympians. But the outfit, with its floral pattern and lace embellishments, made it look like she'd done a bit of DIY-ing with some old curtains.

Judging by this look, it's no surprise her eponymous fashion brand closed the very same year if that's where her style instincts were at in 2018. Thankfully, Ivanka's style has transformed since leaving politics behind.

"Fashion is not by accident with [Melania Trump]," said Bob Phibbs, the CEO of The Retail Doctor, when speaking to The New York Times. "She knows [fashion's] power." So, wearing a jacket with the words "I really don't care. Do U?" on the back as first lady is a mishandling of that power.

What's more, she wore it en route to a child detention center on the Texan border. Again, it's pretty tasteless from Melania, and the internet agreed. "Melania is as thoughtless, feckless, and indecent as I suspected!" a user on X bluntly put it.

Lara Trump, Eric Trump's wife and Donald Trump's daughter-in-law, was repping her family on Memorial Day in 2018. However, the look was pretty in-your-face. The Fox News host wore a MAGA swimsuit that literally said "Make America Great Again" on it. So, no points for subtlety here.

The swimsuit, which is from the Trump campaign's online store, was also just plain boring. It looked like free merch you'd throw on out of necessity during laundry day, not least Memorial Day. That's just one of the worst Lara Trump outfits that totally missed the mark. 

"I got to bust out the coolest belt ever," wrote Donald Trump Jr. on Instagram in June 2018. At least, that's what he thought of the brown leather belt with a detachable .22 caliber pistol on the buckle. "Taking open carry to a whole new level," he continued.

However, the whole thing was a little bit childish. It's the grown-up version of wearing a "Ben 10" watch to high school. It might impress some audiences, but as far as fashion goes, it ain't too chic.

You know about the MAGA hat and now the MAGA swimsuit, but how about the MAGA dress? Well, during designer Andre Soriano's fashion show at the Trump International Hotel in Washington D.C., a white dress with "Make America Great Again!" written down the center in shimmering crimson lettering hit the catwalk.

The gown itself is passable, as it's typical wedding fare. But, as Coco Chanel famously quipped, via Vogue, "Before you leave the house, look in the mirror and take one thing off." In Soriano's case, that thing should've been the ostentatious MAGA slogan.

On a 2018 transatlantic trip to the U.K., Melania Trump donned a striped dress that had some very strange colors. The garment brought together the lesser-spotted combo of navy blue, burnt orange, burgundy, and cream. Yes, all those colors on one dress. The last time we saw that combo was during the Johnny Carson era of "The Tonight Show."

As we've covered, Melania doesn't dress for the weather. Nor is she an expert at dressing for sports, as shown by her playing bowls in Louboutins. Maybe tone it down occasionally, Melania? 

When you hear leather pants, you probably think of big-haired '70s rockstars shredding on a guitar. Well, Melania Trump's bafflingly bad beige leather pants did little to change that perception.

The biggest issue here is that the latte-colored pants duped some online into thinking Melania wasn't wearing anything below the belt at all. As one user on X joked, "[Melania] was in a hurry and forgot to finish getting dressed." That's how well the pants matched her skin tone. Sometimes, certain colors just aren't for you – not that Melania took that advice.

On a visit to SiriusXM in 2019, Lara Trump wore some very unflattering trousers. The pinstriped pants were three-quarter length yet oversized at the same time, leading them to look both too wide and too short. Plus, the bare ankle is a major fashion ick for some.

The other elements of the outfit, including her white top and Converse trainers, are timeless pieces that only serve to make the pants look even more out of place. You've heard of a face for radio. Well, these are certainly pants for radio.

A black-tie dress code is something to be followed strictly. But if Donald Trump's outfit at the Buckingham Palace state banquet in 2019 is anything to go by, he didn't get that memo. One thing's essential for a black-tie outfit, and that's a well-tailored suit.

However, Trump's white waistcoat didn't do this outfit any favors, as it looked way too big and draped far below his waist. He is, after all, one of nine disheveled MAGA men that could use a makeover. And he needed it here, stat!

Although polka dots are synonymous with a modish European look, Ivanka Trump's weren't quite giving that in London. She stepped into 10 Downing Street wearing a white dress with black splodges (dots would be a little kind) and matching monochrome stilettos.

Some British designers, like Cath Kidston, have done a roaring trade with the Dalmatian-like print. Yet, Ivanka's dress was all over the place and featured varying types of polka dot patterns, as opposed to a chicer, monotonous version of the print. Sometimes, less is more.

As they say, be careful what you wish for. But this outfit Melania Trump wore in November 2019 had us wishing hard for more color. The suede, beige ensemble (boots and all) matched her skin tone far too much. Melania's makeup transformation through the years is impossible to ignore, but this look makes everything blend into one, like someone spilled coffee on a Halloween ghost costume.

Given that Melania has a tanned complexion, wearing brown that's too similar to your skin tone is a big no-no. There's a good outfit here; it just needs less brown and a bit more color. 

On a 2019 trip to Bogota, Ivanka Trump made a lunge towards avant-garde fashion that was pretty ghastly. Her olive-colored dress, designed by Colombian native Johanna Ortiz, ironically, made her look exactly like the hors d'oeuvre.

She wasn't helped by her wafting sleeves that, when catching the wind, looked like lily pads or even like she was donning dog cones on her arms. As one user on X quipped, "Just because your dress cost over a thousand doesn't make you a fashion guru." We can't help but agree.

Was Melania Trump giving "Brat" here? Despite the color, not quite; it was, in fact, more akin to a green screen. Against her husband's more classic blue suit, the pleated Valentino number seriously stood out for the wrong reasons.

This dress may have been improved by utilizing the element that makes it a bad outfit: the color. If the MAGA media team had the foresight, then they could've simply used some of Hollywood's finest CGI artists to overlay a better dress atop it. Alas, they did not. 

Jared Kushner is a man who utilizes uniform dressing. We could've picked just about any snap of the then-senior advisor and seen him in his signature skinny suit. However, his slim suiting is less Hedi Slimane at Dior and more head-scratching.

Take this example from a visit to the Oval Office in 2020, where the skinny suit doesn't exactly exude the power needed in a high-end government official. Rather, it looks like the only suit he had in his closet, but it's from his high school prom, and now it's too small.

In 2020, Tiffany Trump took a leaf out of her stepmother's book by donning a gaudy, green dress. What was it with MAGA women and green dresses in the late '10s and early '20s? Although bold greens went à la mode in early 2020, like any trend, there are good examples and bad examples.

This is a bad example. Tiffany's viridescent dress was floral and bright, but it feels like there's way too much going on. From the eclectic cut to the loud pattern, it's too much yet not enough.

Here's how Melania Trump compares to Donald Trump's exes when it comes to handling his ambitions. She would've had to use all her ambition managing skills on January 20th, 2021, a.k.a. the day Donald left office at the end of his first term. Maybe that's why she chose this dress — she had no time for better selecting her wardrobe?

The dress, which featured a bizarre orange, navy, and cream pattern, looked like she had thrown on her favorite wallpaper before skedaddling. Whatever the reason, this was a bad outfit for Melania's (first) finale as first lady.