Miley Cyrus’ Outfits That Were Totally Out of Style

From her days spent filming on a Disney Channel set to winning her very first Grammy, there is no denying the absolute stunning transformation of Miley Cyrus. Though she is mainly celebrated for her unique sound, mixing an array of genres throughout her songs, the singer is also known for her sense of style, to which she has always been open to experimenting with. “Fashion to me is kind of flipping yourself inside out,” Cyrus told British Vogue. “It’s like wearing your heart, wearing your guts, wearing your values, wearing your identity, wearing your pain.” Yet while the singer’s level of fearlessness with fashion is praiseworthy to say the least, some of Cyrus’ looks over the years have not quite hit the mark.

Incorporating fringe, cut-outs, and sheer pieces within her wardrobe, Miley Cyrus can sometimes appear as if she is stuck in the past. Such outdated fashion trends have left the “Flowers” singer looking less than fresh, though some only require a few modern touches to bring new life to the overall outfit. “If a look is outdated, but there’s still one or two elements that can be refreshed and modernized, don’t be afraid to rework them,” fashion expert and celebrity stylist Cindy Conroy told The List. “Pair with current ready-to-wear pieces and you can make an old outfit new.”

Though we will always love the artist for the nostalgia she brings to the table, here are 12 Miley Cyrus outfits that were seriously outdated.

Becoming a coach on Season 11 of NBC’s “The Voice” was a big deal for Miley Cyrus, as the singer was the youngest star, at the time, to snag her very own red chair. Although she would not return as a coach for Season 12, Cyrus was sure to make an appearance for its finale, and performed her lead single “Malibu” in May 2017. Surrounded by a collection of foliage and an earthy backdrop to match, Cyrus could be seen wearing an all-white look paired with natural hair and makeup. The ensemble was made up of a peasant top, complete with puffy sleeves and a peplum at the waist, as well as a pair of white denim shorts which were accessorized with a matching belt.

While there is nothing wrong with an outfit made up of simplistic and classic pieces, Miley Cyrus’ look appears more dated than timeless in this case. The culprit? The singer’s style of top, which has been around for far too long, and by 2017, peasant tops were most definitely a no. “The look is not feeling so fresh this summer,” Ida Petersson, Womenswear Buying Director at Browns, told Elle at the time. “Have we reached peak peasant top fatigue? I think so.”

In June 2017, Miley Cyrus joined Jimmy Fallon as a guest on “The Tonight Show,” where she appeared to pay tribute to her country roots with a denim and gingham get-up. The look featured a busy, red gingham blouse, adorned with ribbons and ruffles, which was further accentuated by a matching pair of open-toed platform heels.

However, according to Vogue, the gingham pattern already had its moment in 2015, making the singer’s overall outfit appear dated and drab. Though Cyrus had paired the patterned pieces with a classic pair of flared jeans, the top and shoes were far too distracting and actually weighed the look down.

Aside from its pattern, Miley Cyrus’ outfit featured another tired trend, as her blouse sat straight across her torso and off her shoulders. Many blue and white pinstripe blouses had actually featured this trend for years, so by 2017, off-the-shoulder tops were starting to look boring and overdone. Not only that, but this style of top rarely lived up to its namesake, making it an easy pass amongst the other choices on the market.

Though fashion does often repeat itself and many trends come back into style, there are certain pieces that scream old-fashioned no matter how much time has passed. This much was true for Miley Cyrus at the 2017 VMAs, who decided to don a poodle skirt during her performance of “Younger Now.” “One of the most iconic elements of 1950s fashion is the poodle skirt,” said Dr. Valerie Steele, Director and Chief Curator of The Museum at the Fashion Institute of Technology (via Sammy D Vintage). Paired with a bright fuchsia playsuit, orange neck scarf, and bedazzled belt to add a little sparkle, the singer’s ensemble looked far from modern as she danced across the stage. Cyrus was even sure to capture the true essence of a poodle skirt by including an appliqué on the front, though it was of her initials instead of the silhouette of the famous dog.

While it was quite clear that Miley Cyrus was aiming to embody the style of the 1950s, there is no denying that her outfit was anything but outdated. In fact, the only time we really see poodle skirts in the wild anymore is right around Halloween, which is probably why the overall look felt more costume-like than anything.

It’s no secret that Miley Cyrus has always been a fan of fringe, a trend which she showcased when she returned as a coach on Season 13 of “The Voice.” In an episode of the show which aired in November 2017, the singer could be seen wearing an all-black, western outfit, which featured a satin shirt embellished with silver star patches and metallic fringe. However, this addition to the singer’s wardrobe did nothing but date the entire look, as fringe had gone from boho to no-go by 2017. “Full-on boho had its moment but it’s time to avoid fringe, gladiator sandals, and oversized sunnies,” Shira Suveyke, Chief Merchant of The Outnet, told Elle that year. “These were great at the time but it’s now going in the way of clean and feminine.”

Though fringe has decreased in popularity, there are ways that it can be updated, which is good news for Miley Cyrus and other lovers of the trend alike. Fashion expert and celebrity stylist Cindy Conroy shared some of her favorite ways to refresh outdated fashion, informing us that we do not have to trash some of our favorite pieces after all. “Infuse modern touches like ‘It’ bags, cargo pants, metallic cowboy boots, or linen cropped jackets and instantly transform less-trendy styles,” Conroy told The List. “It creates a fresh look that’s rooted in the here and now.”

Oversized clothes first came back in style following re-runs of the show “Friends,” yet the trend quickly became the worst enemy for many who tried to wear it. When not styled properly, oversized outfits had the tendency to look downright frumpy and unfashionable, which held true for an outfit worn by Miley Cyrus in 2018. In December, the singer was seen wearing a baggy, plaid suit set, which she paired with a furry, bucket hat and a pair of white Doc Martens. Her homemade crop top was also a few sizes too big for the slender star, making her outfit one that totally missed the mark.

The extremely oversized trend had more than overstayed its welcome, and was actually considered one of the worst trends of 2018. “I love mixing shapes and sizes in your outfit to add texture and visual interest, but swimming in boxy, bulky clothes isn’t doing much for your shape,” Catherine Bachelier Smith of CBS Lifestylist told BestLife. With that being said, fashion expert and celebrity stylist Cindy Conroy suggested taking advantage of tailoring to create a more up-to-date look. “If you find a local dry cleaners or tailor they can adjust just about anything. Change flared pants into slim, long sleeved into sleeveless, billowy blouses into streamlined fits. The list is endless,” Conroy told us.

In February 2019, Miley Cyrus attended the red carpet premiere for “Isn’t It Romantic,” a film which featured the star’s then-husband, Liam Hemsworth. Though Hemsworth could not attend the event due to some personal health issues, Cyrus was sure to make an appearance in his honor. With Valentine’s Day right around the corner, the singer showed up in an all red look, complete with a swipe of crimson lipstick and a slicked-back ponytail. Her Valentino gown featured a long cape, ruffles, and multiple sheer panels, which showed off her lower chest area and legs despite being a full-length dress.

Though the dress was absolutely show-stopping, it was out of style at the time, as ruffles had lost their spot in the fashion world in 2019. Nordstrom Senior Fashion Director, Shannon Schafer, explained to Elle that a simpler silhouette had grown in popularity, and the stiff and billowy nature of ruffles was no longer desirable. Long dresses such as Miley Cyrus’ were now taking on a much more fluid design, making her red carpet attire appear less fashionable than it would have in the past.

While a well-fitted pair of jeans will most likely never go out of style, there are certain trends, when it comes to denim, that need to be left in the past. Jeans with multiple slits and rips, for example, may have been popular in 2018, but wearing overly distressed denim quickly became a fashion faux pas. “It’s two steps away from falling apart,” Rafy Bassali, co-owner of Swank Co., told BestLife, explaining that an excessive amount of holes can take away from the overall coolness of denim. Unfortunately, Miley Cyrus did not get this memo in time for a fashion event in June 2019, as the star arrived at the St. Laurent Men’s SS 20 Show wearing a pair of shredded jeans.

Paired with a shimmery, black jacket and a pair of black boots, the singer’s jeans were not only covered in glitter, but had multiple rips down the leg. The dated trend was quite distracting and made Miley Cyrus’ look appear out of style, even though she had matched the pants with some pretty chic pieces.