Selena Gomez's Most Inappropriate Outfits We'll Never Forget

From Disney Channel starlet to celebrated actor, singer, entrepreneur, and fashion icon, Selena Gomez has become a beloved entertainment industry staple. Beyond her thick, career-building filmography and discography, fans also flock to the A-lister on social media, adoring her relatability. And Gomez isn't afraid to get personal, inviting audiences into her life with heartfelt posts and candid, makeup-free selfies.

Over the years, Gomez has undergone a stunning style transformation and built a reputation as a fashion risk-taker, further inspiring her fanbase. However, it hasn't all been smooth sailing on the fashion front. Like any other young celebrity, Gomez has had to find her aesthetic under the paparazzi's sharp gaze, which means photographic evidence of every outfit that didn't hit the mark. While Gomez is now widely hailed as a sleek fashionista, looking back at her less successful outfits can help remind us that fashion is a journey of exploration that will naturally bring occasional stumbles.

Selena Gomez made her red carpet debut at the 2007 World Magic Awards, but the young actor's look was underwhelming. The pants, heels, and accessories are bland to the point of tastelessness, and the baggy and faded leopard-print top looks a little too familiar — like it's come straight from the racks of Marshall's or Ross Dress for Less. Everybody has to start somewhere, but in 2007, this outfit could have been spotted on any teenage girl and did nothing to emphasize Gomez's budding star power.

Also in 2007, Gomez attempted a similarly casual vibe at the ABC All-Star Party. While the cutesy tee and boots might befit a Disney Channel star from that era, they weren't befitting such a publicized event. To be fair to Gomez, a look back at the fashions donned by other attendees shows many questionable choices, as guests like Miley Cyrus also turned up in then-trendy, now-outdated styles. This awkward blast from the past just goes to show why more classic, timeless styles are perennial red carpet favorites.

Before we let the '00s go, we have to talk about Selena Gomez at the 2008 premiere of "Hannah Montana & Miley Cyrus." This outfit gets points for attempting something interesting, but it's like looking at a Russian doll of denim layers. A blue vest over a black romper over blue jeans? It's a lot to take in. Add the clunkiness of those chunky heels and the painfully kitschy red streaks in her hair, and young Gomez comes across like a fashion time capsule — one that might be better off unopened.

In 2012, Selena Gomez even arrived too casual for her own event. Gomez appeared at her 2nd Annual Charity Concert benefitting UNICEF in a thin, knotted white T-shirt over a dusty rose boho maxi skirt — another outfit that didn't live up to her star status or the gravitas of the charity she was representing. Her accessories didn't elevate the look, either, with the oversized pendant necklace and orchid-pink heels seeming more like afterthoughts than intentional accents.

By 2015, Gomez transitioned to chicer styles, but she struck a sour note at Billboard's Women in Music event in the disjointed combination of a jeweled and feathered cocktail dress and a black, cold-shoulder coat. This pairing was odd enough, but fashionistas also didn't love the dress on its own. Accessorizing with black tights and heels fought against the soft whimsy of the flapper-style frock, cheapening the overall aesthetic. Ultimately, the glittery ensemble had the feel of a figure-skating costume rather than a haute-couture red carpet look.

With her daring and unpredictable fashion, Gomez has stunned at many black-tie events. Unfortunately, the 2018 Met Gala look was less of a success. The theme was "Heavenly Bodies," and while Gomez's diaphanous white Coach gown evoked an ethereal vibe, its heavy ruff of underbust lace gave the dress a strange, maternity-like fit. Moreover, her heavy-handed nude makeup washed her out, eclipsing her natural beauty. And, sadly, her frumpy updo did nothing to save the look, resulting in an ensemble that doesn't reflect Gomez's usual fashion-forward style.

Surprising many, Gomez was named one of the worst-dressed celebs at the 2024 Primetime Emmy Awards. While the dress had potential and a point of view, the finished look fell strangely flat. Despite the transparent cutouts, which should have given Gomez a flirty and risqué edge, her gown came across as stiff and matronly. The heavy burgundy lip and thick chain necklace only weighed the ensemble down further, resulting in a quiet flop.

Gomez has come a long way from her early '00s aesthetic, but her adult style still suffers occasional missteps. The star's ensemble for the 2024 Golden Globes sparked debates, with some viewers loving the look and others considering it one of the worst of the night. The vivid red Armani gown featured a voluminous, asymmetrical hem and a knotted, peekaboo bodice, which ultimately didn't work for Gomez's figure, making the dress a miss for this red carpet. Whether you love or hate this look, it's definitely an unforgettable piece.