Bethenny Frankel's Most Inappropriate Outfits Ever

Age is just a number for Bethenny Frankel. And why not? The reality star activist is in the best shape of her life, and she's not afraid to show it off. However, some of Frankel's inappropriate outfit choices indicate that perhaps just because you can doesn't mean you should.

Bethenny's transformation from 35 to 50 and beyond has been pretty radical. She's gone from wannabe actor and private chef to "The Apprentice: Martha Stewart" competitor to bonafide business mogul and cocktail queen. Frankel's Skinnygirl empire made her the richest "Real Housewives Of New York" star. She offloaded the brand's drinks arm to Beam Global in 2011. However, Frankel's involvement with Skinnygirl continued as she grew other parts of the business.

Meanwhile, her public profile hasn't dimmed much since quitting reality TV. Frankel loves to be the center of attention at all times, especially if any photographers are around. Resulting in her flashing her bare backside for the cameras and turning up to the "Today" show in pajamas and fluffy pink bunny slippers. Frankel also tries to quench her thirsty ego in interviews. "They're calling me Erin Brockovich," she told The Cut in November 2023, referring to her reality TV contract crusade — without expanding on who the mysterious "they" are. Still, Frankel's desire to always be the main attraction is most apparent when it comes to her questionable style, something that's usually guaranteed to turn heads, often for the wrong reasons. We're checking out some of Frankel's most inappropriate outfits ever.

It's painful to tear another woman down. Still, when it comes to Bethenny Frankel's 2020 leather get-up it's a struggle to summon any positives — aside from her figure, which looked amazing, and her sunglasses were fabulous. "Casual Monday," she captioned a photo of the ensemble, which was anything but casual. It comprised a Tom Ford high-waisted leather corset skirt and a bust-baring Balmain crossover cutout top. Oh dear Bethenny, oh dear.

Frankel completed her eye-catching couture with a black face mask that had large red lips embroidered across it (it was COVID-19 days after all). She could have gotten away with the look if she was heading to a swanky nighttime soiree. Still, it has to be deemed an inappropriate outfit for daytime wear, even by Manhattan standards. Plus, she risked catching her death of cold, given it was November.

"C'mon The emperors new clothes," a fan wrote in the comments." I love your cloths and style, but this is not casual!! I'm not sure about this look maybe a bit tooo much it seems busy," another critiqued. "Omg, I wore that same dress to church, on Sunday!!" a third quipped.

Most moms endeavor not to overshadow their daughters, preferring to build them up by making them the center of attention while stepping to the side. However, most moms aren't Bethenny Frankel. In December 2023, the former reality star guaranteed she would hog the headlines by choosing to twin with her then-13-year-old daughter, Bryn Hoppy, for the iHeartRadio Jingle Ball in New York City.

The two were coordinated in red strapless mini dresses with giant bows attached to the bodice top. Frankel's was a super short red and pink check with a tiered bubble skirt, while Hoppy's comprised a block-color slim-fitting sheath. "Jingle ball, jingle ball, jingle all the way!" Frankel captioned a carousel of photos on Instagram showing the two posing with a big pink Christmas tree, with added hashtags #mommyandme, #daughterlove, and #jingleball.

Hoppy revealed what it's like having Frankel as a mom in an interview with "Today" in July 2023. "It's crazy," Hoppy told Hoda Kotb, elaborating, "Like all of the stories and everything," and sharing, "She's strict." Bethenny explained that she orders her daughter to "Shut the program down" when she gets angry with her. "You reach a point, and then you get really mad," Hoppy said. Given it was the teen's first appearance on the show, you'd think the attention would have been on her. But, not so much, as Bethenny, guest-hosting, sat in a skimpy swimsuit with the "Today" logo emblazoned across her chest.

Bethenny Frankel took twinning with her daughter a step further in July 2014. This time, instead of matching clothes, she wore her then-four-year-old daughter's actual clothes — well, pajamas, to be exact. "This is my daughter's nightgown and PJ shorts. Think we're ready to start sharing clothes yet?" she captioned a photo posted on Instagram showing her posing in some teeny-tiny shorts, a frilly pink Hello Kitty T-shirt, and matching furry slippers.

Somebody who definitely didn't think Frankel was "ready" yet? A Manhattan matrimonial judge. "No more pajamas!" Justice Ellen Gesmer warned during a hearing in October 2014. Frankel's attorney, Allan Mayefsky, attempted to brush it off as just a bit of lighthearted fun, but Gesmer didn't see the funny side. "It's not a joke. Her child is not a joke," she said. According to Page Six, Frankel wore pajamas to court, albeit an adult pair this time.

Some commenters on Frankel's Instagram post didn't see the funny side either. "I'm glad the judge set you straight....your kid is not a joke....and also, as a mother to girls, this is not funny. Put on some d**n grown woman clothes. You are a 'public figure' (for whatever reason) and should act as such. If you want to make stupid 'funny' pics..make a private Instagram to share ignorant pics with," one wrote.

Bethenny Frankel went all out for Halloween 2018, dressing as a Wonder Woman angel. "Heaven sent," she captioned some Instagram photos of her otherworldly ensemble. Frankel's Victoria's Secret outfit comprised a diamante headpiece, giant feathered wings, sparkly flesh-colored tights, fluffy white high-heeled mules, and a mesh-paneled see-through all-in-one with frilly panties and a cut-out satin bra.

Frankel went head-to-head with the Kardashian klan, who were also decked out in Victoria's Secret freebies. "Thank you @VictoriasSecret for sending us actual runway looks and real wings to borrow for the night!!! OMG a dream come true! Got to be a Victoria Secret Angel for the night! And Kendall got good practice lol," Kim Kardashian captioned an Instagram photo of the five siblings strutting their stuff like in a semi-naked reality TV version of the "Reservoir Dogs" intro.

Some of Bethenny's Instagram commenters were less than impressed by her super sexy getup. "Oh H**l no like putting lipstick on a pig.... Golden girl attempt VS," one sniped. "It's just that you constantly shamed Carole [Radziwill] for her clothes and style not being age appropriate and then you go and dress as a 20 something lingerie model," another opined. "Got a bit of a porn star vibe there....," a third commented.

Bethenny Frankel wore a decidedly inappropriate outfit to the June 2022 MTV Movie & TV Awards in Santa Monica. Her thigh-skimming red silk skater-style dress, embellished with flowers, was cut frighteningly low at the front, barely covering her bust. Frankel didn't do herself any favors with her cutsie red carpet poses, more fitting of a teen girl on her quinceañera than a grown woman at an event.

That said, Frankel's princess look was kind of appropriate, maybe, given she was presented with the reality royalty award — by Paris Hilton, no less. Still, royalty or not, you know you have an issue when Hilton is more covered up and classily dressed than you. "You and I are OGs in this genre," Frankel said. "And as you know, not everybody fits in the bad b***h genre. It's a genre."

It turns out that Frankel and Hilton have a deeper connection than just being bad b*****s. The former "Real Housewives of New York City" star used to care for baby Hilton back in the day. "This is actually the announcement for our new reality show where Paris changes my diapers," Frankel quipped as Hilton laughed awkwardly. "It's called 'That's Not Hot.'"