Melania Trump's Most Daring Outfits Before She Became First Lady

Melania Trump has certainly undergone a dramatic style transformation over the years. She's morphed from a little-known Slovenian model on the arm of her then-boyfriend Donald Trump, galavanting around New York, showing off the biggest fashion trends from the late '90s and early 2000s. We consider many of her outfits from this era bold mostly because they're revealing, but also they pushed envelopes (and not always in a good way, ahem, fur coat). She loved to don a slinky slip dress that left nothing to the imagination, and rarely covered up her cleavage.

After she became a mother to Barron Trump in 2006, her fashion sense noticeably shifted to something more conservative. There was another monumental shift when her husband announced he was running for president in 2015. Her style became more refined, classy, and elegant, with structured suits and tasteful dresses becoming de rigeur. But her style before she became first lady? Straight up daring.

"Daring" is one way to describe wearing a floor-length white fur coat, which Melania Trump did in 2002. It's a slap in the face to animal rights activists, for starters, but also all-white anything, especially when it's an expensive outfit, which Melania Trump is known for wearing, is always a risk in terms of attracting and showcasing stains and dirt. Her ample cleavage adds to the riskiness of the look, and certainly makes it one we would never expect to see Melania revisit while her husband occupies the White House.

Long before he was attempting to Make America Great Again, Donald Trump was known for his flamboyant life as a real-estate tycoon who loved to have a beautiful woman on his arm. In 1999, that woman was Slovenian model Melania Knauss. The two attended the MTV Video Music Awards in September of that year, with the latter posing in a dress that had a thigh slit that went daringly high on the leg.

Ask any number of fashionistas if they would wear a tube top and cropped pants right now and they'd enthusiastically give their approval for the '90s-inspired outfit. But would we see Melania Trump dare to revisit the look that she wore to a movie premiere in July 1999, complete with tummy-baring crop? Doubtful. We can't imagine the first lady sporting an outfit like this while she's residing at Pennsylvania Avenue.

For a movie premiere in April 2000, Melania Trump wore a black dress that boosted her assets, accessorized with a pair of heels that wove around her slender calves. Though she wore the shoes, which gave a sultry vibe, on multiple occasions, we would guess these daring heels have since been retired, as we cannot picture her wearing them for a state dinner nowadays. For the most part, it's all about Manolo Blahnik and Christian Louboutin stilettos, with the occasional cool sneakers thrown in.

Nothing says newlyweds like wearing coordinated outfits. Donald and Melania Trump, married at Mar-a-Lago in January 2005, headed out to Shaquille O'Neal's 33rd birthday in Miami Beach in March of that year, wearing pops of pink by way of his tie and her dress. Melania's halter-neck dress left little to the imagination, making it a daring outfit choice for the evening out. Side note: When was the last time you saw the first couple in matching outfits?

As first lady, Melania Trump has donned some beautiful suits, from a red Dior number in Paris in 2017, to dreamy cream Dior at the 2018 State of the Union address, to a black belted Michael Kors pantsuit in 2024. We are beyond relieved that her style has evolved into something more elevated than the white-suit 'fit she wore in 2000 to the "Charlies Angels" premiere. The offending element here was the tacky lacy lingerie worn underneath, which is a far cry from the stunning looks she's suited up in as first lady.

This look rates as one of the most outdated outfits Melania Trump has ever worn. The baby doll top also counts as one of her most daring. The look, worn to a fashion show in 2004, featured a sheer camisole-style top that fully amplified the former model's cleavage. Back before she was married to Donald Trump or became a mother, it was more likely that you would see Melania's assets on display than see them covered up.

Now here's a daring outfit that Melania Trump wore before she became first lady that we would never expect to see again. For starters, Melania no longer wears bold earrings like the chandeliers she wore to the Victoria's Secret Fashion Show in 2003. Her form-fitting Dolce & Gabbana dress would never see the light of day this side of the election, and her makeup has evolved from the frosty shades she veered toward two decades ago.

Donald and Melania Trump were once regular fixtures at the famed annual Costume Institute Gala at the Metropolitan Museum of Art. Back in 2012, Mrs. Trump showed off her frame in a figure-hugging Marc Bouwer dress with dramatic shoulder points and a daringly short hemline. Her bold bangs gave an extra element of strength to the look. Will we ever see her back on the guest list at the Met Gala? Time will tell.