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Fashion Fails: The Worst Celebrity Looks of October 2021

Angelina Jolie wearing a suit dress as a movie premiere
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October is a special time of year. The weather becomes increasingly confusing; colourful leaves create a flurry of social media posts that all look the same, and everyday people all of a sudden become the witches they always aspired to be. (Hocus Pocus, anyone?)

Change is in the air, but one thing remains true — celebrities will continue to wear terrible outfits, and we’ll continue to be here to poke innocent fun at their efforts. As the rich and famous begin to prep themselves for the best parties and events that spooky season has to offer, we’ll be here impatiently waiting for some epic Halloween costume blunders.

So, grab some candy (and a sense of humour) and find out which outfits are scaring the fashion sense out of certain celebs this month.

Related: The worst celebrity looks of September 2021

Cardi B dressed in a green onsie for fashion week
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Cardi B, October 3, 2021

Far be it for us to tell Cardi B what to do, but having a baby doesn’t mean you have to dress like a baby, too. This green onesie is a lot to take in, but it’s the bonnet that truly sealed Cardi’s fashion failure fate. It’s also producing some major Willy Wonka vibes, and while the Oompa Loompa’s may have her back with this look, we can’t say the same for us. 

See also: The best memes of Cardi B’s Paris Fashion Week outfits.

Rosario Dawson wearing a black latex dress at an event
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Rosario Dawson, October 4, 2021

You know what they say — one person’s trash is another person’s next event look. At least, that had to be what someone said to Rosario Dawson before further convincing her that a latex black garbage bag-inspired dress was the right choice for the premiere for Hulu’s Dopesick at the Museum of Modern Art. Sometimes bad fashion happens to good people, and there’s nothing we can do but judge them.

You may also like: 10 fall fashion trends that are going viral on TikTok right now.


Scout Willis posing for the camera wearing an all-red '80s inspired outfit
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Scout Willis, October 5, 2021

Sure, it’s hard to stand out when you’re the daughter of famous actors Bruce Willis and Demi Moore, but Scout Willis is looking more ’80s camp than an elegant lady in red. It’s not all bad, though. We love each piece she selected for this outfit, but putting them all together for Paris Fashion Week may have been trying too hard to create a vibe worth clapping for. Instead, we see red — and not in a way that makes us feel full of love for this look.

Related: Celebs bringing back ’80s and ’90s hair trends.

Zendaya wearing a long grey dress with a gold bib as she poses for a step and repeat
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Zendaya, October 6, 2021

Never in our wildest dreams did we think Zendaya would find herself on any fashion fails list — let alone ours — but here we are. Do we really need to point out that the gold bib is the most obvious issue with this outfit? Things could have improved for Zendaya, but the remainder of the dress looks like a material we’ve spent the entirety of the pandemic wearing while we work from home. We’re sorry we had to do it. But can you blame us?

See also: Zendaya’s style evolution from Disney-star to style icon.

Kim Kardashian leaving a hotel dressed in all pink
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Kim Kardashian, October 7, 2021

In more unpopular opinions this week, we are once again picking on Kim Kardashian. It’s not the worse thing we’ve seen her in, but when we think of a pink Barbie dream outfit — this is not exactly what we had in mind. First, it’s the velvet jacked mixed with the sleek satin boot-pants, but mostly it’s those stupid little gloves she insists on wearing. Were wish you better luck next round, Kim.

You may also like: The funniest memes about Kim Kardashian’s Met Gala outfit


Zooey Deschanel in a floral peasant dress at a tv premiere
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Zooey Deschanel, October 8, 2021

This dress is a typical Zooey Deschanel outfit, but we do have one tiny critique for everyone’s favourite manic pixie dream girl. Deschanel wore this floral peasant dress to the season two premiere of We’re Here, an HBO Max series where former RuPaul’s Drag Race contestants travel the United States to recruit small-town folk to participate in a one-night-only drag show. So, we have to ask: did she not get the memo that neon, glitter and sequins were on the fashion menu that evening?

Related: The richest drag queens, according to net worth.

Jennifer Lopez walking in New York with Ben Affleck
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Jennifer Lopez, October 10, 2021

Nobody wants to put JLo on blast, but this leather outfit is too much for her, and we’re not afraid to say it. She’s mixing suede and leather in a way that feels like it’s swallowing her up. And although we are brainwashed to believe that a woman of JLo’s stature never perspires, we can’t imagine this outfit is giving her skin any room to breathe at the beginning of October. Luckily, her arm candy has us distracted enough to let this one go. 

See also: JLo’s style evolution.

Gail King in a multi-coloured striped dress at an SNL afterparty
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Gail King, October 10, 2021 

Oh, goodness. Gail King was either trying too hard or not trying hard enough with this multi-coloured dress topped off with her very own pair of Kinky Boots. The outfit-on-trail was King’s fashionable choice for the SNL afterparty after Kim Kardashian hosted. But it feels more like what King would choose to wear when meeting up for book club with her pal Oprah.

Related: Style trends spotted at the 2021 Grammys.


Cynthia Erivo in a yellow ruffle dress while standing on a red carpet for photographers
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Cynthia Erivo, October 11, 2021 

Cynthia Erivo is not one to shy away from daring fashion statements, and for that, we bow down to the queen. Unfortunately, there is no bowing taking place for this mustard-coloured prom dress circa 2004. From the triangle formation to the unnecessary amount of ruffles — we don’t know whether to present her with a corsage and spike the punch so we can forget about it.

See also: Style trends you didn’t know originated from Black culture.

Gigi Hadid walking in New York in a white oversized suit jacket with yellow sunglasses
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Gigi Hadid, October 11, 2021 

We’re not sure if Gigi Hadid is wearing something so high fashion it’s entirely over our heads — or if she is on her way to pitch an idea to some executives? Either way, this oversized suit jacket means business. It feels too serious for Hadid’s playful nature, and we simply can’t get past the fact that she looks like an extra Martin Scorsese hired for his latest gangster film.

You may also like: Gigi Hadid reveals the sweet beauty secret she’ll teach her daughter.

Regina King in a black sequin dress at an event
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Regina King, October 13, 2021 

It’s not the worst thing in the world, but something about this black sequin number Regina King wore to the premiere The Harder They Fall just isn’t sitting well. And we mean that literally. It’s tight and short and looks like the kind of dress that requires you to remain on your feet at all times or risk showing folks more than they came for.  

Related: Slip dresses are here to stay and this is how to get in on the action.

Emma Watson posing for the cameras in an upcycled wedding dress for an eco-friendly event
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Emma Watson, October 17, 2021

Attendees at the inaugural awards ceremony for the Earthshot Prize in London were encouraged to wear an environmentally-friendly outfit on the green carpet. Emma Watson followed through on that request by presenting an upcycled look created from 10 wedding dresses donated to the charity organization Oxfam. Her intentions were true, but just because she did a good, doesn’t mean Watson is safe from looking bad. 

See also: This is dark academia and it’s everywhere this fall.

Sarah Jessica Parker photographed smoking a cigarette while on the set of the tv show And Just Like That
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Sarah Jessica Parker, October 20, 2021 

This behind-the-scenes photo sent Sex And The City fans into a frenzy of confusion, and now it finds itself here on the worst dressed celebs list. Is it a photo of Sarah Jessica Parker enjoying a cigarette break with protective gloves intact? Or is the once-loved, now despised, Carrie Bradshaw back to her old addictive habits? I guess we’ll be forced to watch the SATC reboot to find out.

You may also like: Sarah Jessica Parker’s style evolution.

Alexandra Daddario posing for the camera at an event
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Alexandra Daddario, October 19, 2021

There is nothing particularly wrong with the dress actress Alexandra Daddario wore to ELLE‘s 27th Annual Women In Hollywood Celebration. Still, if we’re honest (and why wouldn’t would we?), there’s nothing right with it either. It’s just kind of, well, boring, which is frustrating to say out loud since Daddario is anything but boring.

Related: The history of fashion: the most important style moments of the 20th century.

Kristen Stewart casually walking down the street
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Kristen Stewart, October 20, 2021

Kristen Stewart has long been a fashion chameleon. She often blows us away on the red carpet and takes daring risks that almost always pay off. But when it comes to her street style, Stewart takes the fashion road less travelled and plays it casually cool. That easy-going vibe can be seen here, and we’re here for it, all the way down to the ankle. Once we hit those Mary Jane shoes and white socks — we’re all the way out of here.

See also: 10 androgynous style staples you need in your closet


Lisa Rinna wear a red dress and puffer jacket at an event as she poses for the camera
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Lisa Rinna, October 26, 2021

Oh, Lisa. There’s nobody we’d rather pick on this month than a Real Housewife who can bring it just as hard. What Rinna wore to the Neiman Marcus launch of their Celebrate Big, Love Even Bigger holiday campaign isn’t terrible. In fact, it’s very cute and on-trend — if you’re in your 20s. So, for that reason, we’re submitting Rinna to the fails list for doing what she does best: trying too hard.

You may also like: Ranking the Real Housewives by their net worth.

Jennifer Garner caught walking on the street by a photographer wearing a matching outfit
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Jennifer Garner, October 26, 2021

Picking on everyone’s favourite celebrity mom isn’t the classiest thing we’ve ever done, but we can’t help but poke a wee bit of fun at the always sweet Jennifer Garner. This elementary school teacher look is an everyday staple in Garner’s wardrobe, but we fear she took her near-perfect ability to match a bit too far this round.

See also: This is dark academia and it’s everywhere this fall.

Angelina Jolie wearing a suit dress while posing a movie premiere
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Angelina Jolie, October 27, 2021

Angie fell victim to red carpet criticism earlier this month when she had a hair extension blunder caught by nearly every camera in attendance. We want to spare her another moment of critique, but the suit-dress situation she revealed at the UK premiere of Marvel’s The Eternals isn’t helping matters.

See also: Angelina Jolie’s style evolution.

Jen Harley posing for cameras at an event
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Jen Harley, October 27, 2021

If you’re a Jersey Shore fan, then you likely remember the very toxic presence of Jen Harley, the former girlfriend and baby momma of Ronnie Oritz-Magro. If you need a refresher, a quick Google search will tell you every ridiculous detail about the relationship between these two. For now, we’re focusing on the fact that Hartley’s outfit is as dated as her ex’s famous MTV reality show — and we don’t mean that as a compliment.

Related: The worst dressed celebs at the 2021 VMAs.


Katherine McPhee walking down the street with sunglasses on
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Katherine McPhee, October 27, 2021 

Katherine McPhee is your typical girl next door, and we are here for that vibe, but the singer’s recent street style isn’t hitting a high note. Sure, it’s sweet, just like her personality, but the cast of Little House on the Prairie is left wondering why she raided their clothing racks because, well, it’s 2021!

You may also like: Then and now: 10 drastic celeb style changes.

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