Fashion hits and misses for celebs born in October

By Megan Riedlinger 5:52am PDT, Oct 4, 2021

Happy birthday, October babies! Wonderwall.com is taking a look at this month's crop of birthday stars' best and worst looks. First up? Katy Perry! The pop singer, who was born on Oct. 25, has worn some funky fashion in her day, but dressing like a chandelier takes the cake. Katy's 2019 Met Gala look by Moschino transformed her into a real-life walking light fixture complete with a headdress delivering even more light.

Now let's check out our favorite look from the birthday girl… and see more October birthday star fashion hits and misses…

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Our favorite Katy Perry look is a recent one: She wore this lilac confection to Variety's Power of Women: Los Angeles event in Beverly Hills on Sept. 30, 2021. The over-the-top dress from the Schiaparelli Fall 2021 Haute Couture collection featured some of the most dramatic sleeves we've ever seen, as well as a full skirt with a train that trailed after her on the red carpet.

Oct. 21 marks Kim Kardashian West's birthday. Her biggest fashion miss in our book? This Burberry number she wore to the WSJ. Magazine Innovator Awards in 2019. The denim and leather getup had us scratching our heads — from the off-the-shoulder neckline to the oversized sleeves to the boned corset, not to mention how puzzling it was to see denim shorts suddenly transition to navy blue leather pants culminating in pointy-toe boots.

Our favorite Kim Kardashian West look? Her black velvet Vivienne Westwood moment at the 2019 Primetime Emmys. The vintage gown had a fitted silhouette that ended in a diminutive train, and she accessorized perfectly with layered diamond necklaces.

Brie Larson celebrates her birthday every year on Oct. 1. Our least favorite look from the star? This fuchsia-and-red Giambattista Valli number she wore to the "Just Mercy" premiere in 2019. The confection seemed to be comprised of a minidress with a massive structured train that cascaded behind it, delivering a serious high-low hemline effect. Though we didn't love the silhouette, we did love those hot pink pointy-toe pumps she paired it with.

Our favorite Brie Larson fashion moment happened at the 2016 Academy Awards when the star donned this rich blue spaghetti-strapped Gucci number adorned with a ruffled skirt and a sparkly belt at the waist.

We're sorry, Winona Ryder, but we're making you relive this mess of an outfit you wore to the 2020 SAG Awards. The Oct. 29 birthday girl's black Dior moment could have been wonderful — if the frilly tiered tulle ballgown had fewer layers and wasn't topped with a structured black blazer.

For our favorite Winona Ryder look, we've got to take things back to 1997. That's when Winona donned this fabulous pink spaghetti-strapped gown with a matching shawl for the AFI Tribute to Martin Scorsese.

We're never a fan of a half-pant, half-skirt look — even if you're Julia Roberts. She wore this Stella McCartney outfit to the 2019 Golden Globes and it didn't fare well with fashion critics thanks to the weird tan half-skirt that spilled over top her black trousers. Next we'll see our favorite look from the star, who blows out birthday candles every year on Oct. 28.

Hot pink Brandon Maxwell coordinates scored Julia Roberts a fashion hit in 2018 at the premiere of her show "Homecoming." The movie star donned this long-sleeved top and high-waisted trousers combo in the bold hue for a big win that she complemented with tan sandals.

Dakota Johnson blows out birthday candles every year on Oct. 4. As for picking her biggest fashion miss, we've got to go with this Gucci getup she wore to the LACMA Art and Film Gala in 2018. The caped costume-like creation featured long sleeves, a strange sheer panel of fabric from the collar to the neckline and a high center slit.

At the "Fifty Shades Darker" premiere in 2017, Dakota Johnson stunned in a flesh-toned Valentino gown. The spaghetti-strapped frock featured a V-neckline and an A-line silhouette that, while super simple, made a serious impact on the red carpet.

From the high-low hemline to the mix of ruching and leather, we'll never get over the Alexandre Vauthier ensemble that Ciara wore to the 2018 Vanity Fair Oscar party. Though the deep emerald green shade was lovely, there was simply too much to digest with this disastrous confection — including what appeared to be a black leather minidress underneath an otherwise ostentatious ballgown complete with a seriously dramatic train. Next up? A look at a better fashion moment from the Oct. 25 birthday girl.

What's better than hot pink Tom Ford? Ciara wowed in this monochromatic getup — a hot pink jumpsuit with a matching suit jacket over top — at the Victoria and Albert Museum Summer Party in 2018. Finishing off the fabulous look? A pair of white pointy-toe pumps.

We never forget Ashley Graham's birthday — Oct. 30th. But we wish we could forget this Christian Siriano getup that the model wore to the Glamour Women of the Year Awards in 2018. The strapless crop top featured an unnecessary and strange tail detail off the side, which she paired with an otherwise sharp pair of chartreuse wide-legged trousers.

Flawless! Our favorite Ashley Graham fashion moment happened in 2017 at the Miss Universe competition when the model donned this high-necked long-sleeved ankle-length white design by Michael Costello that featured a beautiful sequined design throughout.

Yikes! Oct. 2 birthday girl Camilla Belle donned this disastrous Carolina Herrera number on the red carpet at the Art of Elysium Heaven Gala in 2015. The off-the-shoulder, long-sleeved blue gown not only had a strange silhouette but featured a massive floral motif down the skirt in shades of red, white and blue.

Camilla Belle's best look was also a blue gown — this time a sleek silhouette from Gucci. The actress wore the powder blue frock, which fit her like a glove, to the LACMA Art and Film Gala in 2014.

Wrapping-paper couture? Kelly Osbourne, who celebrates her birthday every year on Oct. 27, donned this strapless Vivienne Westwood number at the Art of Elysium Heaven Gala in 2016, much to fashion critics' dismay. The super-shiny silver and baby blue printed frock gave us serious holiday-wrapping-paper vibes and her dark lip seemed like a strange move against the icy color palette.

Kelly Osbourne delivered her best look at the 2019 Primetime Emmys where she donned this sleek and sophisticated Brandon Maxwell design. We loved the cape-like detail on the sleeves, the high neck and those edgy cut-outs as well as her bright purple hair, which brought a pop of color to the otherwise dark ensemble.