Kellyanne Conway Fashion Fails She'll Never Live Down

Donald Trump's administration has welcomed plenty of interesting additions during his second term in the White House. There's Gen Z White House press secretary Karoline Leavitt, the youngest person to hold the position thus far, and Kristi Noem, the controversial figure Trump named Homeland Security secretary after she made headlines for confessing to killing her dog. But let's face it; it's hard to top former Trump adviser Kellyanne Conway and her indelible contribution to pop culture. The woman who helped Trump win his first election gave her former boss a run for his money when it came to grabbing headlines, creating buzzwords, and spawning memes. 

She hit the ground running, coining the infamous phrase "alternative facts" during an interview with Chuck Todd on her second official day as counselor to the president. She had Anderson Cooper rolling his eyes on air, made up a fake terrorism incident called the Bowling Green massacre, and casually violated federal ethics rules to peddle Ivanka Trump's fashion brand on television. And, of course, we can't forget that Conway inspired numerous hilarious "Saturday Night Live" skits starring the brilliant Kate McKinnon, including the now-iconic "Chicago" spoof. 

But while they were often overshadowed by her controversial interviews and unflinching loyalty to Trump, Conway also brought some interesting style choices to the White House. Of course, her ensembles didn't get anywhere near the attention that Melania Trump's surprisingly meaningful looks or Ivanka Trump's outfits did. But those who paid attention to what the former presidential adviser was wearing will know she served up a few good looks and plenty of questionable ones before Conway made the shocking announcement that she had decided to leave the White House ahead of the 2020 Republican National Convention, many of which she'll never live down.

Kellyanne Conway got her first taste of being a viral meme in January 2017 when her outfit for Donald Trump's inauguration was brutally clowned on social media. Described by the controversial political consultant, during an interview with NBC 7 San Diego, as "Trump revolutionary wear," Conway showcased her version of method dressing at the event by donning a red, white, and blue military-style wool coat. She paired it with white pumps, a bright red hat, and matching leather gloves, resulting in a look so costume-y it bordered on satire. But while the controversial politician was clearly going for a patriotic outfit, she missed the mark by a mile. Not only was her $3,600 coat made by an Italian brand — Gucci — and an Italian fashion designer — Alessandro Michele — but it was created as an homage to London, so it's less Yankee Doodle and more Paddington Bear.

Memes and jokes about Conway's look quickly did the rounds. One user on X, formerly known as Twitter, posted a meme featuring a photo of her alongside the text: "When the inauguration is at noon but the revolutionary war reenactment is at 3." Another tweeted: "Congrats to our new Ambassador to Toyland." The official "Daily Show" account joined in too, posting, "Kellyanne Conway dressed as the era Trump wants to take America back to." 

However, the staunch Trump loyalist stood by her choice and brushed off the jokes about her pricey coat in the process. "Sorry to offend the black-stretch-pants women of America with a little color," Conway scoffed to The Hollywood Reporter in response to the memes. Hinting that she wasn't surprised by the backlash, the politician proudly called herself "the face of Donald Trump's movement."

Like her former reality TV star boss, Kellyanne Conway had some memorably petty moments during her time at the White House, and often went overboard even when "less is more" would have been the smarter option. For example, while speaking to reporters in 2019 regarding Robert Mueller's report on the investigation into Russian interference in the 2016 presidential election, Conway repeatedly gloated over the fact that it failed to prove the Donald Trump collusion allegations instead of keeping things professional or just staying mum. 

"We're accepting apologies today, too, for anybody who feels the grace in offering them," she said at the time, per The Hill. However, this wasn't limited to her words as the former Trump aide often did way too much when it came to her outfits too. The base ensemble, which consisted of low-rise black skinny jeans and a loose black top, was basic but not bad. Pairing it with just the cheetah-print pointed-toe pumps and gold hoop earrings wouldn't have been completely acceptable. Unfortunately, she apparently thought that wasn't enough as she also wore a cheetah-print belt — over her top, mind you — and a long, chunky necklace. 

The loud accessories didn't even match the cheetah-print pattern and shades of her shoes, ruining the illusion of an intentional look. Conway also threw on a long, stark white coat embossed with geometric shapes, making the whole look downright confusing and strange. We're not sure what aesthetic the divisive Republican was going for here, but we do know the result wasn't giving White House spokeswoman. Rather, it read more like mob wife about to start her shift at the hospital. However, we're not sure actual mob wives would approve of how Conway styled these pieces together either.

Kellyanne Conway's love of prints doesn't stop at cheetah; her wardrobe is full of bold and crazy prints of all different kinds. Unfortunately, the former presidential aide's efforts to nail bold colors and prints have seen more fails than successes. Conway's first year as senior counsel to the president was particularly rough in this regard. In June 2017, she went to Capitol Hill dressed in a low-cut, long-sleeve maxi dress so eye-searing that if she had picked it up for $5.99, she still would have overpaid. Its bodice and skirt featured a design that looked like blue, green, and gray scales from a distance. However, the sleeves and the hem clashed horribly with the rest of the dress, featuring a print of what appeared to be mechanical mice engulfed in flames. Creative? Yes. Hideous? Also yes.

Sadly, this ensemble was just the first of many. In the same month, the politician donned a sleeveless red dress with a white floral print that looked like it was directly taken from a tablecloth for then-South Korean President Moon Jae-in's visit to the White House. Then, just a few months later, she stepped out in a yellow-orange silk shirt that was far too attention-grabbing for a White House press conference, instead resembling something you'd wear to the club. 

Its print, which featured a mix of cheetah, zebra print, and colorful squiggles and circles, was painful to look at. But it hasn't all been bad. Conway has churned out some good looks when she's not mixing loud prints with equally loud colors. During an August 2017 press conference, she chose a simple light blue dress with a dark blue floral print that complemented her light blonde hair and made her look years younger.

If there's one accessory Kellyanne Conway can't do without, it's a huge statement necklace. The political consultant has accumulated a considerable collection, showcasing tons of designs over the years, most of them big and bright enough to overpower her already loud outfits. Aside from that chunky cheetah-print necklace, Conway was also spotted wearing a multi-layered necklace (above left) in 2016. It was seemingly meant to be a statement piece, considering she paired it with an all-black outfit, but the politician was probably better off not wearing it as the clunky necklace made the overall ensemble look cheap.

The rest of her collection isn't much better. One of Conway's favorites is a thick beaded blue ombre necklace (above right) that she's donned several times in public, typically with a blue outfit. In 2019, she paired it with a bright blue wrap dress and electric blue pointed-toe flats, resulting in an outdated look that seemed straight out of the late 1990s or early 2000s. The staunch Republican also wore a memorable necklace for the then-Romanian president's visit to the White House in 2017: A gold piece that looked like several large snowflakes stringed together. 

Aside from the shade being an almost exact match for Conway's blonde hair, the necklace looked uncomfortable to wear due to the pointed ends around the neck. However, just as the Republican politician has remained loyal to Trump, she just can't let go of her necklace collection and even seems to be actively adding new pieces. During a January 2025 event, she chose a layered necklace featuring stones of various shades of blue held together by black strings. It's just as outdated as her other blue necklace, but thankfully a bit more toned down and not as in-your-face.

Fortunately, Kellyanne Conway left the big necklaces at home for a July 2020 interview and press conference, but the replacement wasn't exactly much of an improvement. She wore a simple royal blue dress and metallic blue pumps, but the pièce de résistance was her bright orange silk scarf with a pink flower print. The combination of the fitted dress and scarf was giving flight attendant realness, except no airline would mix these particular shades of blue and orange in the one uniform. While they are indeed complementary colors, her chosen shades were all so bright that the outfit became hard to look at. 

To make matters worse, the political consultant paired the ensemble with a bright red handbag that matched neither her dress nor her scarf. This was one of the last outfits Conway showcased before announcing her decision to quit her position as Donald Trump's White House counselor that August. In a statement obtained by CNN, she explained that she and her husband George Conway, an outspoken critic of her former boss, had chosen to slow down in their work in order to dedicate more time to their children — especially during the COVID-19 pandemic. 

"[George and I] disagree about plenty but we are united on what matters most: the kids," she noted. The politician has since become a contributor at Fox News and even scored her own program, "Here's The Deal with Kellyanne Conway." Her TV gigs have evidently come with a stylist as she's been leaning toward the monochromatic and clean girl aesthetic — with no big, chunky necklaces in sight.