Inappropriate Outfits Olivia Culpo Has Been Caught Wearing

While Olivia Culpo usually looks out of this world, even the former Miss Universe makes questionable clothing choices on occasion. After winning her crown in 2012, Culpo became a style star, gracing the runway for the first time at Zadig et Voltaire's New York Fashion Week presentation in 2017. She later told The Daily Front Row, "That was so fun and nerve-racking and I'm glad that it's over."

That daunting catwalk experience didn't diminish her passion for fashion. Culpo has launched a clothing line with her sisters, and she's become known for her willingness to rock risqué looks. She also has no qualms about sacrificing her bra for style's sake. She's also suffered to look good. Speaking to Glamour UK in 2017, she revealed that one of her Emmys dresses was so tight that she passed out while wearing it. But right before recalling that incident, she said, "I actually think that there are no mistakes in fashion. Fashion for me is self-expression and I will never say that what I was feeling or wearing at a particular time was wrong."

Culpo does sometimes ask her millions of Instagram followers for their opinions on her outfits, like when she used her Story to see if they agreed with her dad that a denim miniskirt was "not age-appropriate." Per Page Six, 77% of her followers disagreed with him. But he's not the only one who has accused his daughter of wearing inappropriate clothing.

If a celebrity wants to get dressed up in a designer gown, they can always find some excuse to do so in Hollywood — from premieres to award shows to charity galas; the options are endless. This is why it never makes sense for stars to commit the egocentric etiquette breach of eclipsing a bride on her wedding day. We'll concede that Olivia Culpo's style sin actually occurred the day before her friend Devon Windsor walked down the aisle in St. Barts. However, many critics still found her revealing outfit in poor taste.

For what was possibly a rehearsal dinner, Culpo rocked a PatBo dress that was almost bridal white. It displayed a lot of skin, thanks to its wide, plunging neckline and side cutouts. It also featured fringe trim and a mesh skirt that revealed Culpo's silky, high-waisted underwear. When she shared photos of the look on Instagram, some of her followers felt like she could have been mistaken for the woman who was supposed to be the center of attention. "Did anyone tell her that she isn't the BRIDE?!!!" one Instagrammer wrote. "Eh it's the bride's day. Is she not ur friend?" another commented. At least Windsor is an accomplished model, so she wasn't being outshone during a rare opportunity to dress up. She also didn't seem concerned about being upstaged by Culpo when they posed together in cheeky bikinis with their names printed on them during her wedding weekend.

Models can get away with wearing just about anything on the runway — unless that runway is located at an airport. Olivia Culpo found this out the hard way when she was informed that her sporty outfit was apparently too fly for the skies in 2022. In a series of posts on her Instagram Story, Olivia's sister Aurora Culpo chronicled her clothing catastrophe. Per E! News, It began when the siblings and Olivia's then-boyfriend, San Francisco 49ers running back Christian McCaffrey, were preparing to board an American Airlines flight to Cabo San Lucas, Mexico. "They call her up to the desk and tell her that she needs to put a blouse on. Otherwise, she can't get on the plane," Aurora recalled. So what was this outfit that was so outrageous that Olivia wasn't allowed to wear it while sitting in a plane seat for a few hours? A black V-neck bralette, bike shorts, and an oversized cardigan.

On her Instagram Story, Olivia revealed that she had to borrow McCaffrey's hoodie to be permitted to board her plane. He was then forced to tuck his arms inside his T-shirt when he got cold during their flight. Olivia shared a photo of her chivalrous and shivering boyfriend and wrote, "When you freeze bc ur lady dress inappropriate AF. Exactly how Jack from the Titanic died. LMAO." For the record, the dress code for American Airlines passengers is vague: "Dress appropriately; bare feet or offensive clothing aren't allowed."

In 2020, Olivia Culpo and Christian McCaffrey headed to Miami for the Super Bowl showdown between the Kansas City Chiefs and the San Francisco 49ers. (This might be why you experienced a sense of déjà vu when you tuned in to see Taylor Swift and Usher in 2024.) McCaffrey was not playing in the game that year, as he was still with the Carolina Panthers, so he and Culpo were able to spend the entirety of Super Bowl weekend partying and attending events. Unfortunately for Culpo, she chose the wrong white Georges Hobeika dress when she accompanied McCaffrey to the 9th Annual NFL Honors ceremony. 

On Instagram, Culpo shared a fashion horror story that started with the influencer making a valiant effort to hide the fact that she was wearing underwear. In addition to a plunging neckline that reached her stomach, her dress had a slit on the right side that extended up to her ribcage, so any underwear with straps on the sides would have been visible. "Have any of you ever worn stick-on underwear? Because I did today," she wrote. Normally, this would have kept her underwear completely hidden, but instead, they ended up in full view of anyone standing around Culpo when their sticky bits failed. "It fell off when I was about to do the carpet ... literally ... on.the.carpet," she wrote. She concluded her post with some helpful fashion advice. "Beware of stick-on underwear and Miami humidity."

Olivia Culpo realized that the white Vivienne Westwood mini dress that she picked out for her 2023 engagement party was too small when she had to ask Christian McCaffrey to help her get the back zipped up. She captured the moment of truth for a GRWM TikTok video. "This is just the world's absolute tightest dress of all time," she said as McCaffrey gave her a helping hand. He was successful, but disaster struck when the zipper broke, leaving the back open down to her waist. "That's never happened to me before," Culpo said of the wardrobe malfunction. 

Somehow, McCaffrey and some other members of Culpo's "damage control team" were able to get the back of the damaged dress closed back up. Culpo revealed that she had no clue how they did it but praised her fiancé by saying, "He fixed my dress. He's a jack of all trades."

If Culpo's draped dress had been unfixable, maybe she would have rocked it anyway. Speaking to GQ in 2012, she revealed that she won her first big pageant title, Miss Rhode Island, while wearing a torn gown. But in that instance, the damage was not of her doing. "I wore a $20 dress that I rented with a hole in the back," she said. "It still looked cute, but nobody would have known that I rented it for twenty dollars." Her engagement dress is worth over 100 times that amount.

In January 2015, Olivia Culpo walked the Miss Universe pageant red carpet with her boyfriend at the time, Nick Jonas. The singer had told E! News that he penned his song "Jealous" after catching a guy checking out Culpo's butt, and he was invited to perform it at the event. We're guessing the Jo Bro kept a close eye on the eyes of other guys as Culpo glided past them in her white Michael Costello dress. The generously cut neckline showcased a lot of cleavage, while sheer panels on the garment's trumpet skirt extended up to her hips. She was a member of the judges' panel, putting all the pageant contestants at risk of having their gowns majorly upstaged.

Some of Culpo's Instagram followers thought that her dress was the wrong choice for the event, and others simply didn't like it. "It's like, girl, we know you're hot, but you don't need to show us in how many ways all at once," wrote one critic. Another commenter opined, "You look like a half-naked mermaid." The dress was also giving off strong bridal vibes, and apparently, Culpo had marriage on her mind during the show. Jonas later told The Sun (via OK!) that she believed he was going to pop the question when he serenaded her during his "Jealous" performance. "Her face was in full panic," he recalled. Culpo hasn't yet scrubbed that moment from her Instagram account.