Paris Hilton's Killer Legs Couldn't Save These Awful Outfits

With a persona perpetually attached to her hijinks in the early 2000s, the transformation of Paris Hilton has been truly stunning. Going from a bratty reality celebrity to an advocate for bettering youth facilities with questionable practices, Hilton has shown that she's more than just someone with an iconic catchphrase. However, the "Simply Life" star has had some struggles along the way, especially when it comes to finding fashion and styling choices that can properly display her killer legs.

With a physique as toned as Hilton's, it makes sense that she would like to show it off as often as possible. Unfortunately, most of the outfits the "Infinite Icon" singer tends to reach for feel like costumes instead of curated. While there's much to know about Hilton, how she presents herself seems to be stuck in a bit of a rut. Caught between wanting to enjoy the freedom of adulthood and trying to stay on trend, Hilton unfortunately fumbles more often than not. From confusing outfits going in too many directions to overly risqué looks, there have been plenty of times that not even Hilton's killer legs could save her styling.

Though Paris Hilton's amazing physique and toned legs were on display in this November 2022 outfit she wore to the LACMA Arts + Film Gala in Los Angeles, it still couldn't be saved. The draped cowl top matched with the belted waist was most likely supposed to play into a toga-inspired look, but it came across as overly confusing. Having the cut out of her hip matched by the high slit could have been a fun way to play with proportions, had the rest of the outfit had a little less going on.

In April 2025, while attending the Neon Carnival at Coachella in California, Paris Hilton wore one of her more inappropriate outfits. While the patterned mesh onesie certainly has a sultry vibe to it, especially with her legs on display in such an overt way, the rest of her styling throws the whole look off. The shimmering white boa looks partially made of plastic, cheapening the complete outfit in an unflattering way. Plus, the shin-high boots cut off Hilton's legs at an awkward spot, drawing too much attention to the questionable footwear.

Presenting at the 2025 MTV Music Video Awards in New York, Paris Hilton wore an outfit that felt like a precursor to what landed her on the worst-dressed list for the 2026 Golden Globes afterparty. Even with her killer legs on display, the rest of the outfit feels too on-the-nose. The chains covering her little black dress look heavy and annoying to be seated next to in a crowd. While her high ponytail and overall styling might be Hilton trying to pay homage to Madonna in the 80s, this outfit can't seem to claim a single or realistic era.

While attending the 2025 TikTok Awards, Paris Hilton wore a scandalously short skirt to show off her amazing gams. However, the rest of the outfit simply couldn't be saved due to poor styling, with her dress ultimately looking like a Halloween costume. The shimmering red of her skirt looks like a combination of crushed velvet and sequins, while the black strips appear to be made of cheap pleather. All in all, this look was feuding with itself more than Hilton and Lindsay Lohan ever feuded with each other.

Though Paris Hilton has worn some iconic outfits, the one she stepped out in at the 2026 Women's Wear Daily Style Awards in Santa Monica didn't live up to the hype. Had she gone for one look instead of the two her outfit is competing to be, she might have nailed it. The animal print dress is a bold statement in and of itself, but when paired with the sheer tights and top, they're at odds with each other. Plus, the fact that her tights stop at the ankle makes Hilton's killer legs look shorter than they really are.

Spotted mid-twirl on the red carpet for the January 2026 world premiere of "Infinite Icon: A Visual Memoir" in Los Angeles, Paris Hilton did her net worth dirty by wearing an outfit that looked overly cheap. The dreamy bubblegum pink comes across as overly cutesy and princessy, especially when combined with her bold, silver heels. Though the high slit adds a bit of drama, the silver appliqués on her dress and the sheer draping at the end make it look like Hilton was on her way to compete on "Dancing With The Stars" instead of attending her own premiere.