Jill Biden Outfits That Just Didn't Work

More often than not, Jill Biden gets it right with her fashion choices (remember that stunning 2024 DNC outfit?) But, much like Ivanka Trump's outfits that missed the mark, the former first lady proved having designers falling over themselves to dress you — and a no doubt impressive fashion budget — still doesn't guarantee a great outfit.

Being one of the most visible people in the world during her time in the White House meant Jill had to think hard about her outfits, which she admitted came as a surprise. "It's kind of surprising, I think, how much commentary is made about what I wear," she told Vogue. She also admitted the intense spotlight on her clothing forced her to look beyond the usual big-name fashion houses to lesser-known creatives with their fingers on the pulse. "I like to choose from a diverse group of designers. When I was planning my Inauguration outfits, that's one of the things I considered," she said. But, no matter how much thought went into them, there are still a few outfits in her past that just didn't work.

In 2022, Jill Biden took matchy-matchy to a whole new level when she attended a Black History Month event in the White House. Jill appeared alongside then-President Joe Biden in a below-the-knee black-and-white polka dress with a blazer in the exact same material.

Though we appreciated Jill had fun with patterns instead of relying on the classic block colors we often see in political fashion, wearing the same print in two garments created a distracting, dalmatian-esque look that made us go cross-eyed. Even her red pumps weren't enough to tone down and ground the look. This outfit caused such a furor it prompted one X, formerly known as Twitter, user to declare, "Jill Biden has the worst fashion sense of any First Lady in history." Ouch.

We wouldn't go quite that far though, as Jill proved she knew how to execute the look in a more complementary way the year prior. The former teacher wore the same dress during a trip to the U.K. with her husband to meet then-Prime Minister Boris Johnson and his wife, Carrie. That time, though, Jill dialed down the busy print by pairing it with black court shoes and a black blazer with the word "Love" emblazoned across the back. Not only did the message of unity make that outing of the dress far superior to the other, it was also far less distracting.

When Jill Biden and Joe Biden hosted a Cinco de Mayo reception in the White House's Rose Garden in spring 2024, Jill's outfit didn't fit with her usually polished wardrobe. She wore lime green heels with a flowy, long-sleeve, button-up collared dress that matched Joe's blue tie and navy suit, but it didn't meet Jill's usually impeccably tailored standard.

Though the material belt around her waist stopped the look being too frumpy and highlighted her shape, the pleated bottom of the skirt appeared crumpled and limp. That was odd seeing as the event was held at Jill and Joe's famous home, so it's unlikely the garment got creased in a car ride over. Equally, the extra material on the bottom swamped her 5-foot-6-inch frame. Instead, we'd have recommended the then-first lady wear something a little more form-fitting to avoid adding extra bulk and create a more complementary silhouette.

Jill Biden took a fashion risk in 2011 when she attended a Mother's Day event in the White House. Though the star looked youthful in a bright pink dress, it was simultaneously ahead of its time and dated. The vibrant shade wouldn't have looked so out of place 12 years later amid the summer Barbie obsession of 2023, but it also would have been ideal for an '80s prom.

Although some fashion houses experimented with shoulder pads in 2011, Jill's oversized, rounded take felt too vintage coupled with the bold satin material, which wasn't exactly a huge trend at the time. The shiny fabric wasn't the most flattering either because the skirt was tapered and folded over her thighs to accommodate the panel around her waist, which resulted in extra material gathering around her hips.

The sequin look Jill Biden wore in 2024 would have been perfect for a party, but it felt out of place for the Human Rights Campaign's 2024 Los Angeles Dinner. Every inch of her long sleeve, Sergio Hudson top was covered in large, loose sequins that shone black, silver, and gold, which felt too distracting for a serious event. She accessorized with sparkly drop earrings and wore her hair in an up-do to let the sequins shine even more. Fortunately, Jill knew to keep her bottom half understated to balance out the bold sequins; she opted for wide-leg black pants with a chunky, black waist belt featuring a large buckle. But it still wasn't enough to dial down all the sparkle.

If the then-first lady wanted to bring a little glam to her look in a way that better fit the theme, the navy Ralph Lauren pantsuit she wore later that year to the White House reception honoring Italian American Heritage Month would have a better pick. The beaded embellishments were much more subtle and would have been more appropriate for an event designed to inspire social change.

Jill Biden brought fun fashion to the White House's LGBTQ+ Pride Month celebration in 2021. Unfortunately, her finished look was just too busy. She wore Dolce & Gabbana's patchwork dress, which featured a clashing mishmash of patterns such as white and red flowers over a pink background, black polka dots over a white background, a separate, larger floral print, and stripes of light brown and pink — the result was just as confused as it sounds.

It's thought Jill wore the long sleeve look as a way to symbolize unity between different lifestyles, but that wasn't enough to save the dress in many people's eyes. "Sorry guys, that dress is hideous. It doesn't matter the designer, its fugly. The sentiment... [sounds] lovely. But that doesn't change the fact that is not at all pretty," one X user wrote. 

There were ways to achieve the same effect in a more polished way. As part of Dolce & Gabbana's spring-summer 2021 fashion show, the fashion house also showed off the Multicolor Patchwork Dress. The trumpet sleeve, mid-thigh length garment featured square patches of floral and leaf patterns, which would have given Jill a similar aesthetic but in a polished and uniform way more fitting for a first lady.