The Most Questionable Fashion Choices at Melania and Donald Trump’s 2005 Wedding

New York City’s former mayor Rudy Giuliani attended the Trumps’ wedding with his then-wife, Judith. However, as a plus one, she nearly stole the show. She went for a monochromatic look in all white, which serves as the top place in the ultimate guide of what not to wear to a wedding. Not only that, but she opted for a top that resembles a sherwani, a garment worn by men to weddings in parts of South Asia. She paired the jewel-embellished coat with matching slacks, making for a wedding guest look that completely missed the mark.

Melania and Donald Trump had a winter wedding, but in Palm Beach. So, it’s hard to lock down the weather they were having on their special day, especially because of some of the guests’ ensembles. For instance, journalist Katie Couric arrived in an Emilio Pucci halter dress with white, black, pink, and green geometrical patterns. The former “Today” anchor paired the dress with a lime-green fur shawl. Not only was the look confusing in terms of body temperature, but it was giving more of an ’80s-disco vibe than a wedding-guest dress.

Television personality Kathie Lee Gifford decided on an adorable Ralph Lauren magenta floor-length gown with a ruched neckline. She wore minimal jewelry, did a dewy and natural makeup look, and wore her blond tresses in spiral curls. She finished off the look with a matching shoulder bag and an orange scarf, which is precisely where the issue arises. Gifford’s look was far from ugly, but the pink-and-orange color combination only reminded us of one thing: the Dunkin’ Donuts logo. Let this be a sign that you should always double-check your color palette; you never know what coffee shop you could be representing.

Billy Joel was the highly-anticipated performance at Donald and Melania Trump’s wedding, but his then-wife’s ensemble might’ve made them re-think the invite. Chef and cookbook author Katie Lee opted for a chevron-patterned halter dress with a plunging neckline. Additionally, the multi-colored gown featured pink and yellow stripes below the bust and above the skirt. Lee also kept the accessories to a minimum, wearing a pair of simple dangling earrings. Overall, the cut of the dress was giving “cover-up over a bikini during a tropical vacation.” Certainly pretty, but perhaps not the best option for a wedding.

Star Jones was another attendee of the Trump wedding in January 2005 who wasn’t sure what the weather was going to look like. She likely chose her look based on the fact that it was a winter wedding — not the fact that it was in balmy Florida. The lawyer and journalist decided that she wanted to be covered head-to-toe in gold sequins with a long-sleeved, floor-length gown, pairing it with a fur shawl just in case. Climate aside, wearing that amount of sequins and jewels certainly gives glitz and glam, but almost to the point where the iridescence overshadows the bride.

Heidi Klum is no stranger to a worst-dressed list, as she made her way onto our list of the most inappropriate outfits in iHeartRadio Music Awards history for her 2019 look, and unfortunately, the track record shows that the supermodel has had more misses than wins in the fashion world. For the Trumps’ wedding, she wore a Karl Lagerfeld dress designed for Chanel, but there was entirely too much going on. The gown was tattered at the sleeves, featured a feathered bow on the chest, and had a pattern reminiscent of white-and-black flowers … we think.