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The Style Evolution of Trump's Leading Ladies

Melania Trump: Then

Melania Trump: Then

Before stepping into the political spotlight, Melania Trump was already well-known in fashion circles. As a successful model, she graced runways and magazine covers with her glamorous and high-fashion looks. In the 1990s and early 2000s, Melania's style blended European chic and American boldness. She often favored sleek evening gowns. 

Melania's early style was characterized by a daring approach to fashion, making bold statements that have gotten her in trouble later on. She favored colorful form-fitting gowns and anything luxurious. What else can you expect from an upper-class model and socialite?

David Lefranc/Sygma/Getty Images

Melania: Now

Melania: Now

As First Lady, Melania Trump's style evolved into a more refined and sophisticated aesthetic. She became known for her elegant and polished looks, often drawing comparisons to former First Ladies like Jackie Kennedy. Melania's wardrobe choices are now characterized by classic silhouettes, muted colors, and impeccable tailoring. 

 

She often opts for high-end designers, including Dolce & Gabbana, Dior, and Ralph Lauren, showcasing a preference for timeless and elegant pieces. But her boldness landed her in hot water in 2018 when she visited migrant children separated from their families at the U.S.-Mexico border wearing a fast-fashion jacked Zara that said "I REALLY DON'T CARE, DO U?" on the back. Yikes!

 

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Ivanka: Then

Ivanka: Then

As the eldest daughter of Donald Trump, Ivanka has always been in the spotlight with her business endeavors and fashion sense. Before joining her father in the White House as a political advisor, she had her own fashion and jewelry line. As a 2000s socialite, Ivanka often embraced chic dresses and high-end brands. 

Her early style was marked by a youthful sophistication, incorporating trendy elements with a classic twist, often including wore bold prints, bright colors, and statement jewelry.

Rubenstein, photographer Martyna Borkowski/Ivanka Trump/CC BY 2.0 DEED/Flickr

Ivanka: Now

Ivanka: Now

As a senior advisor to the President, Ivanka Trump's aesthetic evolved into something more understated. She now favors more conservative silhouettes and muted colors. Ivanka's current wardrobe includes elegant sheath dresses, tailored blazers, and sophisticated separates that reflect her role as a professional in the political arena as opposed to a socialite fashionista. 

Her fashion choices are more restrained, focusing on professionalism and elegance rather than making bold statements. Despite this shift, Ivanka maintains a touch of her signature style through carefully selected accessories and luxury trends.

Gage Skidmore/Ivanka Trump/CC BY 2.0 DEED/Flickr

Tiffany: Then

Tiffany: Then

Tiffany Trump initially gained media attention for her slightly grunge, trendy style. The youngest daughter of Donald Trump from his second marriage to Marla Maples, Tiffany has been less in the public eye compared to her siblings. However, when it comes to fashion, she is not one to shy away from making a statement.

In her early years, Tiffany was often seen in playful pieces like high-waisted jeans and crop tops. She embraced various fashion trends, from bohemian chic to grunge rock, and was often spotted wearing something new at parties. Early on, her style centered on partying, which relied on boldness to embody a fun and carefree aesthetic. 

(Image via Instagram)

Tiffany: Now

Tiffany: Now

As Tiffany matured, so did her fashion sense. She probably had the biggest evolution compared to her siblings. Tiffany's style has evolved from being more party-focused to a more polished and elegant look. She now favors a more sophisticated and polished look, suitable for her status as a public figure and law student. 

Like the rest of the Trump women, she now often opts for neutral colors and understated accessories, reflecting a more refined and professional image. While she still enjoys experimenting with fashion, her choices are now more deliberate and mature. Her entire family is in politics now, for the most part!

Andrew Harnik/Getty Images News/Getty Images

Kai Madison: Then

Kai Madison: Then

Kai Madison Trump, Donald Trump’s granddaughter from his son Eric and his wife Lara, has grown up in the public eye, and her style has evolved from cute and playful children's wear to more trendy fashion choices as she entered her teenage years. In her younger years, Kai’s wardrobe was filled with adorable dresses, colorful outfits, and playful patterns.

Like any young girl, she often wore coordinated outfits with her siblings. At just four years old, she is already showing signs of inheriting the family's love for fashion.  

(Image via Instagram)

Kai Madison: Now

Kai Madison: Now

As Kai Madison transitions into her teenage years, her style is becoming more fashion-forward. She enjoys simple jewelry, monotone colors, and clean, white dresses. She is beginning to embrace more mature fashion choices, often seen in stylish dresses, trendy accessories, and chic casual wear.

Her outfits now incorporate more contemporary elements, including stylish footwear, on-trend bags, and carefully selected jewelry, especially as she hard-launched into the political arena at the Republican National Convention. Basically, you can see her fashion choices reflected in sorority girls around the nation!

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Lara: Then

Lara: Then

Lara Trump, wife of Eric Trump, has always had a penchant for  the classics. UIn her earlier years, Lara's style was characterized by a blend of Southern charm and New York sophistication. She often wore fitted dresses, chic separates, and stylish casual wear that didn't draw too much attention. 

Lara’s early style was marked by a preference for the timeless and subtle, which is a quality other Trump women seemingly lack. Her fashion choices were practical, suitable for her roles in television production and as a fitness enthusiast.

(Matt AJ/Matt Johnson/IMG_5045/CC BY 2.0 DEED/Flickr)

Lara: Now

Lara: Now

In her current role as a political figure and media personality, Lara Trump’s style has evolved to reflect her high-profile status. She now favors more trendy looks that are still respectable but has leaned away from things strictly timeless. Now, she's seen in tailored dresses, structured blazers, and elegant evening wear.

Now, her fashion choices reflect a balance between professionalism and approachability, with an emphasis on timeless elegance and understated glamour. Lara continues to impress with her poise in an attempt to look laid-back and relatable.  

(Gage Skidmore/Lara Trump/CC BY-SA 2.0 DEED/Flickr)

Kimberly Guilfoyle: Then

Kimberly Guilfoyle: Then

Before her involvement in politics, Kimberly Guilfoyle was a television personality and attorney. In her earlier years, Kimberly often embraced eye-catching fashion choices, including vibrant colors, bold prints, and statement accessories. 

She was characterized by a confident and dynamic approach to fashion, favoring figure-hugging dresses, stylish suits, and glamorous evening wear. Kimberly’s early fashion sense reflected her bold personality, making her a standout figure in the world of television and law.

(Gage Skidmore/Kimberly Guilfoyle/CC BY-SA 2.0 DEED/Flickr)

Kimberly Guilfoyle: Now

Kimberly Guilfoyle: Now

As a political advisor and public figure, Kimberly Guilfoyle’s style has evolved into a more professional aesthetic, but her personality still shines through. She now favors elegant and tailored outfits, but s;he rarely is caught wearing anything but a low-cut dress. 

Her fashion choices now attempt to prioritize sophistication, but you won't see her ditching the bodycon silhouette anytime soon, even to be taken seriously by the public. It's a fine line between staying true to her bold personality and being continually "professional."

(Gage Skidmore/Kimberly Guilfoyle/CC BY-SA 2.0 DEED/Flickr)

Vanessa: Then

Vanessa: Then

Vanessa Trump, the ex-wife of Donald Trump Jr., was known for her approachable and relatable style during her marriage. In her earlier years, Vanessa often opted for casual yet chic outfits, favoring jeans, blouses, and simple dresses.

She preferred the down-to-earth approach, suitable for her roles as a mother and public figure. Vanessa’s early fashion choices were marked by a preference for comfortable and stylish pieces that reflected her active lifestyle, but she didn't shy away from trends or flaunting her body when attending a party, modeling gig, or red carpet.

Jemal Countess/WireImage/Getty Images

Vanessa: Now

Vanessa: Now

Since her divorce, Vanessa Trump’s style has evolved to reflect her independence and renewed sense of self. She now favors more sophisticated and fashionable looks, often seen in elegant dresses, tailored suits, and stylish casual wear. V

She experiments with her current wardrobe, includes a mix of classic and contemporary pieces, and rarely draws attention to herself with bold pieces anymore. Vanessa continues to impress with her polished and modern appearance, embodying a confident and stylish approach to fashion.

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Ivana: Then

Ivana: Then

Ivana Trump, Donald Trump’s first wife, was a fashion icon in the 1980s and 1990s. Her style was characterized by opulence and glamour, often seen in luxurious fur coats, bold jewelry, and dramatic evening gowns. Ivana’s fashion sense reflected the extravagant spirit of the decade. Think bold colors, patterns, and statement everything.

Her early style was marked by a fearless approach to fashion, embracing the excess and glamour of the era. Ivana’s fashion choices made her a standout figure in the social and fashion scenes, embodying the luxurious lifestyle of the Trump family.

Chip Somodevilla/Getty Images News/Getty Images

Ivana: Now

Ivana: Now

Before her death in 2022 at 73, Ivana Trump’s style had evolved to a more modern aesthetic, but she didn't lose any confidence with age. She still has elegance and glamour, rarely taking the "understated" approach. 

Bodycon dresses, low-cut necklines, and lacy adornments were signature pieces of every outfit. Even when she was out on the town, she sported fun, bold snakeskin prints. 

Patrick McMullan/Patrick McMullan/Getty Images

Marla Maples: Then

Marla Maples: Then

Marla Maples, Donald Trump’s second wife, was known for her relatable-yet-glamourous style in the 1990s. Her fashion sense was characterized by a blend of Southern charm and Hollywood glamour, often seen in chic dresses, jeans, and elegant evening wear.

 

Marla’s early style reflected a more down-to-earth approach to fashion, favoring practical and fashionable pieces that showcased her natural beauty and elegance. Her fashion choices were marked by a preference for classic designs and subtle details, reflecting her Georgia roots.

Vinnie Zuffante/Archive Photos/Getty Images

Marla Maples: Now

Marla Maples: Now

In recent years, Marla Maples’s style has evolved significantly to reflect her commitment to a holistic and wellness-focused lifestyle. Embracing a more relaxed and comfortable approach, Marla has transitioned away from the high-fashion looks of her earlier years to a wardrobe that prioritizes both functionality and well-being, like leggings, breathable tops, and sneakers.

She also likes bohemian-inspired dresses with flowy silhouettes, earthy tones, and intricate patterns. Accessories such as layered jewelry, wide-brimmed hats, and woven bags further enhance her boho-chic look, adding a touch of personal flair to her more "grounded" way of living. 

(Image via Instagram)