9 Rachael Ray Outfits That Were Seriously Outdated

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During the peak of her TV career, Rachael Ray was celebrated for her vibrant personality, relatability, and expertise in connecting with fans. Ray was also known for her many on-air blunders, kitchen hacks, and simple, no-fuss cooking. However, she's never been famed for her fashion-forward approach to style. Far from it, in fact. Ray seemingly prioritizes comfort above all else, plumping for high street brands and clothing that's cozy, cutesy, practical, and — some would say — frumpy.

Ray did have a stylist while filming her self-titled talk show; however, they mirrored her personal tastes rather than advising otherwise. Something that's not all that surprising given Ray's reported diva behavior and love of control. "My friend, Cara Jammet, is the stylist for our show, but our tastes are very similar, and we like shopping together," Ray told an audience member who complimented her on her attire in May 2019. "Many of the things that I wear in life, I would wear here, but, generally speaking, Cara's got me covered. Literally." As far as Ray's superfans are concerned, she can't put a fashionable foot wrong. However, other viewers beg to differ. "She looks so frumpy, why?" one asked on the show's Facebook page. "Rachel needs a makeover her clothes are terrible," another opined.

There are plenty of fashion fails that we're sure Ray wishes we'd forget about. Or perhaps not, given that she continues to bust out with the dowdy and drab duds.

Rachael Ray looked more like an elderly grandma going to afternoon tea with the knitting circle ladies than a top-rated celeb chef and daytime talk titan when she attended the Vulture Festival at Milk Studios, New York, in May 2018.

Ray's black knitted dress with large silver adornment surrounding its high neck left much to be desired in the style stakes. It definitely fell way short of what you'd expect a keynote speaker to wear when addressing the audience at a cutting-edge pop culture celebration.

The dress did have crochet detailing, which is all the rage once again, thanks to COVID-19 lockdown boredom leading to a resurgence of the needlecraft; however, back in 2018, it was still equated with late 20th-century hippies. Still, Ray did attempt to jazz things up with a pair of metallic silver boots. Sadly, they just added to the overall outdated 70s outfit vibe, though.

Bermuda shorts first became a "thing" in the 1920s and 30s, popularized by Western tourists looking for cool (in the temperature sense) attire while hanging out in the British colonial hotspot. Over the years, they've remained a wardrobe staple in various styles before enjoying a major resurgence in the mid 2020s, with Miu Miu and Dries Van Noten among the high-end brands featuring Bermudas in their Summer 2025 collections.

So, you'd think Rachael Ray would have been bang on trend when she was spotted rocking a knee-length pair while strolling around Manhattan in June 2025. Hmpf, not so much. Unfortunately, her baggy and crumpled khaki drawstring Bermudas and matching jacket screamed more "Orlando tourist!" than snazzy stylista.

Alternatively, if Ray had added a pith helmet, bushy but well-manicured moustache, and a lovely cup of tea, she'd have fitted right in with the 1930s colonial crowd.

People may have it all wrong by thinking Rachael Ray's outfits are seriously outdated. Perhaps, in fact, she's actually a fashion trailblazer, a step ahead of Anna Wintour et al, championing and reviving outdated trends years before they officially make a comeback.

The principle of Occam's razor would indicate otherwise. The simplest explanation is that, yes indeed, Ray's outfits are just outdated — and like a stopped clock is right twice a day, her outmoded attire is guaranteed to be on point again sometime.

Such is the case with the fringe hem jeans she wore in March 2019 while leaving the "Good Morning America" studios in NYC. The style was hotter than Ray's jalapeño popper corn dog waffles back in the "Me decade." And, sure enough, six years after she was seen rocking them, 70s-style jeans were top of the trend lists once more. Still, there is no explaining away Ray's white patent go-go boots, though.

When Rachel Ray mounted the stage, mic in hand, to entertain the crowd at Mike's Amazing Burger Bash, she was clad in a graffiti-covered jacket and sneakers. A style that could have — perhaps? probably not — been seen as cred if she was about to spit some rhymes at a mid-80s NYC hip hop club.

However, she wasn't. Instead, Ray was at the 2025 South Beach Wine and Food Festival in Miami Beach, Florida.

And, given that the graffiti was scrawled all over a leather blazer jacket, the sneakers looked like they were big-box store label circa 2022, and she was wearing a midi skirt, Ray's look was way more Vanilla Ice than Run–D.M.C.

Rachael Ray was understandably thrilled to win the Daytime Emmy Award for Outstanding Informative Talk Show in May 2019. She posed for the cameras backstage, smiling widely while proudly holding the gilded trophy in her hands.

However, even the glimmering gold statuette and her bright white teeth couldn't distract from Ray's seriously outdated and truly out-there outfit — comprising a navy frock that appeared to be made from polyester, with an unflattering knee-skimming asymmetric hem and a sparkly top that included a V-neck net insert and glittering fringe epaulets.

It made for an overall aesthetic of part The Beatles' 1960s "Sgt. Pepper's Lonely Hearts Club Band" combined with Johnny Weir at his most divalicious mid-aughts figure-skater stylista best.

The outfit Rachael Ray wore for a May 2019 filming of her daytime talk show wasn't just outdated and frumpy; it was also bewildering and inexplicable. "This little doodad, this dress, and this sweater are from Rag & Bone," Ray told an audience member about the mismatched mess she was wearing. "And they would look lovely on you too," she continued.

Perhaps they would. Maybe they also would have looked lovely on Ray if she'd chosen to wear the high-neck multicolor striped sweater and vibrant floral print dress separately rather than together.

"Rachael is truly the worse dressed talk show host on TV," a viewer commented on a YouTube clip of the show segment. "Plz get help w wardrobe," another pleaded. "She needs a new stylist," a third decreed.

Rachael Ray's stylistically challenged clothing choices reached an all-time outfit low in October 2023. She attended the Food Network New York City Wine & Food Festival Blue Moon Burger Bash at Pier 86 when she committed the fashion felony.

Wait, scrap that. Ray actually hosted the event, making the faded black denim ankle-skimming capris, silver sparkly top, boxy black leather blazer, flat black lace-ups with white wedge heel, black horn rimmed glasses and, erm ... black trilby hat ensemble she plumped for all the more perplexing.

If you were to search for "the most unflattering and frumpy outfit I could possibly wear," it's highly possible a photo of Ray in the ghastly getup would pop up. That said, you'd likely come up with the same result if you searched for "1980s Danny DeVito trilby hat photos."

Rachael Ray's button-front shimmery crushed velvet jumpsuit would have ensured she fit right in while performing on a Las Vegas stage with Elvis Presley in the early 70s.

However, the same couldn't be said when addressing the crowd at a New York City Food Network Event in the mid-aughts.

Unfortunately, the celeb chef proved the point when she wore the one-piece, paired with a pair of white sandals, to host the October 2014 Rachael Ray's Feedback: Chefs And Cocktails event at The Bowery Hotel.

Rachael Ray was dressed to impress when she hit the red carpet for Sonya Sklaroff's "A Love Letter To New York City" solo exhibition and book release in April 2022

However, exactly who she hoped to impress with the bizarre black and gold pattern trim Moroccan caftan and flat black booties she chose to wear to the event is an utter mystery.

"Its voluminous shape and heavily-printed nature might render it unappealing, but its often-plunging neckline and side slit detail lend just the right wink," Harper's Bazaar wrote of the garment in July 2013 along with a selection of photos of stars lounging around in caftans, including a sultry 1972 Elizabeth Taylor, an achingly stylish 1980s Studio 54 Bianca Jagger, and a perfectly polished late 60s Jacqueline Bisset. Sadly, though, you'd be hard-pressed to describe Ray's caftan attire as anything other than frumpy and outdated.