Throwback Jennifer Lopez Outfits That Completely Missed The Mark

Jennifer Lopez is a fashion icon who's worth $150 million. It's not just us saying it; the Council of Fashion Designers of America officially recognized Lopez's "longstanding and global impact on fashion" in 2019 by giving her the Fashion Icon Award. She has more than earned the honor, having served iconic look after iconic look since rising to stardom in the '90s. There's that green, leaf-print Versace dress, which led to the birth of Google's image search function, and her 2000 MTV Video Music Awards look comprising a white crop top, low-rise jeans, and bandana, which were quintessential early 2000s staples.

While Lopez does have stylists who help her craft her looks for red carpets, music videos, and appearances, the "Hustlers" actor plays a major role in her own styling. She told Vogue in February 2024 that her then-stylist Andrea Lieberman advised against the green Versace dress when she was choosing a 'fit for the 2000 Grammys because it had already been donned by a few other famous faces. But Lopez insisted on wearing it to the awards show anyway, resulting in her making fashion and pop culture history. "She completely trusts us, but also has a point of view and knows what works for her. It really is the perfect partnership!" one of her current stylists, Rob Zangardi, told Vogue in 2021.

But even the most fashionable of style stars don't always get it right, and Lopez is no exception. She's got the best stylists working with her, many top fashion designers eager to dress her, and her own fashion sensibility to guide her choices, so it's rare to see a flop J.Lo look, but surprisingly, they do exist. Over the years, there have been more than a few Jennifer Lopez outfits that just didn't work.

For the most part, Jennifer Lopez's outfits have typically highlighted her figure, from bodysuits and bodycon gowns that show off her hourglass shape to two-piece dresses that reveal her ripped abs. And why shouldn't they? The "On the Floor" hitmaker continues to work out regularly to stay toned. This is why it's tragic when an ensemble does absolutely nothing for Lopez's body. A classic example is this black leather dress, which became one of J.Lo's most controversial moments. She wore it to the fashion benefit hosted by designer Tom Ford for the AIDS Project Los Angeles (APLA) in Santa Monica, California, in June 1997.

From the chest up, Lopez's dress looked perfectly fine, featuring a backless design and thin straps that were a staple of the late '90s. But the design made it appear as if there was excess fabric around her middle, which in turn made the dress look like it wasn't tailored to Lopez's body. It's unclear who exactly put Lopez in the dress. The event came around a year before she began working with her former stylist, Andrea Lieberman. But whether it was Lopez's or another stylist's decision, the ill-fitting outfit didn't seem like the best choice for a then-rising star who'd just had her breakout role with "Selena."

Jennifer Lopez has rocked both maximalist and minimalist outfits over the years. She's proven she can pull off monochromatic looks like the beige dress and coat ensemble she wore in an Instagram snap from January 2024, as well as over-the-top designer outfits like the massive fur coat, harem pants, and top with a plunging neckline which she wore to a taping of "The View" in February 2024. But there's over-the-top and then there's way too much, and the latter was unfortunately the case for Lopez's look for the 2004 MTV Video Music Awards at the American Airlines Arena in Miami.

The singer's strapless taupe dress alone was already doing too much; it featured random lines of bronze-colored sequins scattered across the bottom half and multiple white, brown, gray, and red pieces of fabric hanging from both the left and right hips. But adding the wide-brimmed hat, heels with large black feathers, and huge statement earrings, bangles, and rings made it a fashion mishap that not even a style icon like J.Lo could pull off.

Jennifer Lopez has given the world some great hat looks over the years, such as the cowboy hat and Ralph Lauren leather dress she wore to the 2021 Met Gala, and the fascinator she paired her ab-baring black-and-pink gown with for the 2023 iteration of the fashion event. But the headpiece she sported at the 2001 MTV VMAs was not one of these legendary accessories.

For the awards show, Lopez wore a short off-the-shoulder, cheetah-print dress, a wide belt tied around the hips, and a pair of thigh-high leather boots. However, she bizarrely chose to complete the ensemble with a floppy tan hat — like she had to go to the farmer's market at 4 p.m. and then the club at 7 p.m. The singer redeemed herself by choosing simple jewelry and nude makeup that accentuated her gorgeous features, preventing her from veering off into the "too much" category. But overall, the ensemble was still confusing. Despite the fashion miss, 2001 was a big year for Lopez career-wise, with the artist topping the Billboard Hot 100 with two different singles, "I'm Real" and "Ain't It Funny," both featuring Ja Rule.

Jennifer Lopez and her stylists appear to be big fans of lace. The superstar looked gorgeous and was on theme in a white floral-lace minidress for a screening of her 2022 movie "Marry Me." In the same year, she was photographed looking ethereal in a lavender lace dress and glittery platform heels for an outing with her daughter Emme and Ben Affleck's daughter Seraphina in New York City, according to the Daily Mail. However, Lopez hasn't always been able to pull off lace outfits.

In April 2015, Lopez looked ready for a wedding at the Billboard Latin Music Awards in Miami, but not in a good way. While it did show off her fit figure, her white lace jumpsuit looked more like a tablecloth for a vintage-style wedding than something fit for the bride. The white silk cape, while not offensive, failed to improve the outfit.

Fortunately, it wasn't Lopez's only outfit that night. The bedazzled pink crop top, pants, and skirt overlay she wore while performing a heartfelt tribute to Selena Quintanilla later during the awards show looked like the perfect modern take on the late singer's iconic look.

If there's one thing Jennifer Lopez knows how to do — besides live a lavish life — it's rock silver. The color beautifully complements her skin tone, and she's had some truly iconic silver looks, from her sparkly minidress at the 2010 Grammy Awards to her stunning Schiaparelli gown at the 2024 Met Gala.

Sadly, Lopez served face but not looks when she attended a Tom Ford fashion show in Los Angeles in this short silver and black dress back in February 2015. Despite featuring only two colors, the dress managed to look messy and overwhelming in a way that screams more gaudy than avant-garde. The crochet lace design on the neckline and hem of the dress gave it a gothic vibe, but it becomes too much when paired with the silver bumps all across the dress. The addition of black fishnet-stocking shoes certainly did not help.