Now that the world has begun to turn again and celebrities are (safely) out and about to live their most fashionable lives, we thought it was time to bring back some… tasteful takes on what they wore. It’s no secret that the fall season is upon us. And with the onslaught of pumpkin spice everything and the hunger for picking more orchard apples than we can possibly consume, we’re eager to see what fall style disasters await us in the world of celebrity red carpets and street looks.
See also: The richest supermodels in 2021, by net worth.
It’s important to note that while we may poke some fun at this month’s looks, we want to preface the following by stating that we agree fashion knows no bounds. This is especially true if you happen to be a celebrity with a bottomless bank account and countless designer options at your fingertips. However, these facts can’t keep celebs safe from critical observation. Because sometimes you need to be the one friend who is willing to speak up and say — “… maybe, no?”
So, for better or worse (who are we kidding — mainly worse), here are the best of the worst in fashion fails for September. May the fashion gods forgive us, for these big-name stars have most definitely sinned.
Related: 10 hot new beauty picks you can buy this September.
Camila Cabello, September 1, 2021
It pains us to do this because it’s not the first time our dear Camila has found herself on our fashion fails list, but alas, here she is again. It’s not an entirely terrible look, but it’s not the version of a fairytale princess we envisioned for the Miami premiere of Cinderella. Cabello plays the lead role of our darling Cinderella, so it’s fitting that she would show up in a gown fit for a ball. Her skirt full of tulle was the perfect version of a puff pastry we wish we could eat. It had the potential to take our breath away, but Cabello dropped the ball by pairing it with a basic tee usually reserved for the gym. Thankfully, she had the best accessory in tow to distract us, the one and only Prince Charming — Shawn Mendes.
Related: 10 fall fashion trends that are going viral on TikTok right now.
Lake Bell, September 1, 2021
Are we here again? Is buffalo plaid making a comeback and nobody chose to talk about it? These are, of course, rhetorical questions. Everything comes back around and, for Lake Bell, that meant bringing the mid-2000s back in plain sight at the Miami premiere of Cinderella. This particular plaid pattern was already a lot when we showed it off with our fashion scarfs and button-downs, but creating a floor-length dress is moving in a direction we can’t support. It’s possible she confused her dress with the more commonly approved buffalo plaid PJs, but it’s much too early to begin celebrating the holidays. Maybe she was just confused about the time of year? It’s been a tough one for all of us.
You may also like: Bad Y2K hair trends that won’t be be coming back.
Anna Dello Russo, September 1, 2021
Here we have Anna Dello Russo at the Venice International Film Festival serving us pretty in pink. We don’t want to play the age-appropriate card because, well, it’s 2021, and we’ve all grown enough to know that’s gross — but if this isn’t a dress fit for a prom, we don’t know what is. Furthermore, it’s the prom dress you likely begged your parents for, wore with pride, then looked back on 20+ years later and regretted every single ruffle staring back at you. Thankfully, Russo is no stranger to fashion critique since she’s well known (and loved!) for her unconventional fashion choices. As a fashion journalist and the editor-at-large for Vogue Japan, she should get a pass, but we just can’t let her get away with this one.
Related: See these 10 stars show off their wolf cut hairstyles.
Milena Smit, September 1, 2021
This outfit Milena Smit wore at the Venice International Film Festival wants to be cool, but that’s part of the issue. It’s trying just a little too hard to be cool, and the patterned leg is as distracting as a Magic Eye book plucked directly from our childhood. Is it leggings? Boots? Nylons? Pants? After careful examination, we’re sorry to report that we still have no idea what’s happening to the legs in this look. Are the shoes attached? Or is that part of the optical illusion that continues to plague us? The jacket is effortlessly cool; we’ll give Smit that much, but if anyone can crack the case of the patterned legs — give us a ring to discuss!
See also: Gossip Girl fashion cues we’re taking from the 2021 reboot.
Kirsten Dunst, September 1, 2021
Patterns on patterns is a trend. It’s a big trend, and when done well, it can stun an audience, but we’re feeling a bit more stunned than we’d like with Kirsten Dunst’s outfit at the Venice International Film Festival. The style is on point. The pleated skirt, jacket and belt combo are adorably proper, but the colours in these mixed patterns are a little too close in hue for us to provide a standing ovation. The more you look at it, the more you begin to forgive Dunst, but then you get to the shoes and become confused again. Here’s hoping she can Bring It On the next time.
You may also like: 10 high heel hacks that will save your feet.
Cynthia Erivo, September 3, 2021
This is high fashion. There’s no doubt about that, but the foil is just… a lot. To point out the obvious, it looks like the leftovers that have been wrapped in your fridge for weeks, and that’s not something you want to hear even if you are pushing designer trends on a fancy red carpet at the Venice International Film Festival. Also, is it heavy? Because Erivo appears to be holding it, and we’re not convinced it’s because she wants to, but because she has to, or the entire thing will just fall to the floor. If comfort was the goal, Erivo might have walked away with tired forearms.
Related: All the best red carpet looks of 2021.
Kristen Stewart, September 3, 2021
It’s with great pain that we add Kristen Stewart to this list. Often praised for her bold fashion risks across red carpets everywhere, Stewart may have slipped with this outfit she wore at the Venice International Film Festival. It’s cute and all, but it reminds us of a PJ set most often appreciated during a quiet night in with a lover. It’s equally confusing since Stewart is attending the festival to promote her work as Diana, Princess of Wales, in the highly-anticipated film Spencer. We’re not sure if it’s the fact that Diana had such incredible style that’s leaving us so judgy or if it’s the simple fact that this outfit is just not working for Stewart, but either way it gets the royal thumbs down.
You may also like: The coolest gal pal in Hollywood: Kristen Stewart’s style evolution.
Maggie Gyllenhaal, September 3, 2021
Maggie Gyllenhaal doesn’t often land herself on best dressed lists, but she usually isn’t the worst either. That said, she doesn’t get a free pass with this look she gave us at the Venice International Film Festival. It’s giving us school teacher vibes, but we’re also confused with the nun energy happening here. If she ripped the white sleeves off ahead of walking down the red carpet, she might have been able to save herself from this list, but alas, here she is, and we’re sending our prayers as a result.
See also: 19 of the most expensive dresses of all time.
Kate Hudson, September 5, 2021
Kate Hudson! How dare you bring us this tragedy to critique! She’s usually oozing with a cool factor that you can’t deny, but this dress situation Hudson brought to the Venice International Film Festival is not it. The colour is too bland and nearly washes her out, but perhaps blending into the crowd was her plan? We can’t assume that much, but what we can do is offer Hudson a grace period and hope she doesn’t bring us something this dull again because telling it like it is hurt us, too.
Related: Selena Gomez reflects on her Met Gala self-tan fiasco.
Katie Holmes, September 8, 2021
What in the hell happened here? There appears to be some effort involved, but it’s almost as if Holmes gave up at some point while putting together her outfit for the Vacheron Constantin Flagship Grand Opening. We have many questions about the main focal point of this look. Is it a bodysuit, swimsuit or two-piece top under that frumpy button-down? We still don’t know. What could have been sleek and sexy became too casual — and we’re not even talking about the white sneakers that so obviously do not vibe with this look. It doesn’t scream “cool” the way she and we want it to, but we know she tried, and at the end of the day that’s all that really matters… right?
You may also like: Style cues to steal from ‘90s teen dramas.
Chloe Bailey, September 12, 2021
Planning red carpet outfits is hard work. We don’t speak from experience, of course, but we have to assume that selecting the perfect apparel for a highly publicized event is not without its stresses and challenges. We also acknowledge that it’s been a minute since celebs last found themselves in a sea of attention-seeking event carpets, but singer Chloe Bailey phoned it in at the 2021 VMAs. This dress is reminiscent of scrap foil on a high school art room floor, and we’re not giving her a passing grade.
See also: The worst dressed celebs at the 2021 VMAs.
Avril Lavigne, September 12, 2021
It would seem Avril Lavigne found her outfit for the 2021 VMAs at the intersection of the mid-2000s and a sales rack at Hot Topic. The Canadian singer can’t seem to let go of her pop-punk aesthetics, but continues to flirt with designer fashion and girly personal touches by adding varying levels of sparkle and bedazzle. We love a punk rebel with a soft edge, but even an open heart couldn’t save Lavigne from being here.
Related: The pop-punk renaissance is here, thanks to Olivia Rodrigo and Willow Smith.
Kim Kardashian, September 13, 2021
When it comes to stealing everyone’s thunder, Kim K is there for better or worse, and this time around — it’s reached a fevered pitch. Instead of over-analyzing the outfit she presented at the 2021 Met Gala, we’re happy to summarize. This outfit is working the most famous Kardashian sister more than she is working it. But does any critique (good or bad) matter? At the end of the day, Kim knows how to create a buzz just by showing up, and for that, we applaud her.
You may also like: The funniest memes about Kim Kardashian’s Met Gala outfit.
Kim Petras, September 13, 2021
Kim Petras really put us in a tough spot this month. The singer and songwriter arrived on the VMA red carpet in a black latex face mask that quickly made her an ideal candidate for our fashion fails list, but her horsing around at the 2021 Met Gala sealed the deal. The giant horse head attached to her chest created a distracting visual that felt more like the 2019 theme “Camp: Notes on Fashion” versus this year’s “American Independence” theme. And while we appreciate her efforts in bringing the horse costume to life, this look doesn’t have us placing any bets.
See also: The best and worst dressed celebs at the 2021 Met Gala.
Whoopi Goldberg, September 13, 2021
Please send your condolences to us, because we’re fearing the worst after adding Whoopi Goldberg to our fashion fails list, but be honest — can you blame us? This puffy cape-meets-dress-thing is essentially a purple people eater and it’s about to swallow her whole. We wish the infamous actress and television personality could talk her way out of this ruffled mess, but there aren’t enough words to convince us she’s right this time around.
You may also like: Get the look: a complete breakdown of Rihanna’s Met Gala makeup.
Aidy Bryant, September 19, 2021
The adorably funny Aidy Bryant really tried to bring the Christmas spirit to life with this outfit at the 2021 Primetime Emmy Awards, but we think the dress, in particular, should have been left unwrapped. Setting aside the fact that the outfit is a bit too casual for our taste, we’re wondering if we would feel differently if the dress and accessories weren’t screaming holiday hues — but chances are, we wouldn’t.
Related: 10 fall fashion trends that are going viral on TikTok right now.
Kathryn Hahn, September 19, 2021
Hey Kathryn, 2005 called and would desperately like you to return your oversized belt. Seriously, who told her that it would be a fab idea to bring back such a silly trend on such an essential red carpet? Furthermore, how did Hahn’s ribs and chest feel when she attempted to take her seat at her assigned Emmys table? Perhaps she had to remove the belt each time she sat down, but nobody should have to work that hard for a statement piece.
See also: The best and worst dressed celebs at the 2021 Emmys.
Emma Corrin, September 19, 2021
Hmmm, where do we begin here? First of all, we aren’t the only ones to come for Emma Corrin in this confusing style choice showcased at the 2021 Primetime Emmy Awards, so we can’t feel all that bad! If she wanted to break free from her likeness to Princess Diana after wrapping The Crown, mission accomplished! It’s a cross between a monotone wolf and a cast member plucked from The Handmaid’s Tale, and the biggest question on everyone’s mind is — why?
You may also like: Is The Crown fact or fiction? uncovering the truth about Charles and Diana.
Gillian Anderson, September 19, 2021
Gillian Anderson may have taken home the award for Best Supporting Actress for her role in The Crown at the 2021 Primetime Emmy Awards, but she definitely didn’t snag a trophy for best dressed. While there isn’t anything particularly brutal about this look, we can’t help be feel she phoned it in. Maybe she assumed she wouldn’t win? Or maybe this tank and pantsuit was a bad attempt at DIY, and a backup option wasn’t available so close to crunch time.
Related: The history of fashion: the most important style moments of the 20th century.
Amy Poehler, September 19, 2021
This frumpy look attempted to bring together two chic pieces, but the fit completely off, and we’ve lost Poehler’s feet in the mix — a major fashion faux pas! In the past, Poehler has been an awards show host with her best buddy Tina Fey in tow, so one might assume Poehler would know a thing or two about dressing the past. All of that knowledge went seemingly out the window for the 2021 Primetime Emmy Awards.
See also: All the Oscars fashion trends Gen Z loves.
Beanie Feldstein, September 26, 2021
Sweet Beanie Feldstein blew us away with her retro-inspired shimmer dress at the 2021 Primetime Emmy Awards, but it would seem she took a different route when planning her lime green debut at the 2021 Tony Awards. We’re giving this dress’s top and bottom design the green light, but the middle section of Christian Siriano’s frock has us proceeding with caution.
You may also like: Red carpet fails: the worst Oscar dresses of all time.
Chrissy Teigen, September 26, 2021
A lot is going on with this disco ball disaster. Sure, the Tony Awards make room for the loudest red carpet outfits, but the ruffled pink sleeves on this sparkly ensemble are too over the top, even for Teigen — which says a lot! Of course, we don’t want to be catty, but since Chrissy has made a career out of bullying folks online, we assume it’s fair game to be as brutally honest as she usually is.
Related: Get Chrissy Teigen’s glow with this simple acne product.
Lauren Patten, September 26, 2021
Lauren Patten attended the 2021 Tony Awards in support of her role as Jo in the Broadway version of Jagged Little Pill. The good news is that her speech about thanking her trans and nonbinary friends and colleagues who engaged in complex conversations and dialogue about her character Jo was award-winning. The bad news is that her Beetlejuice-inspired look on the red carpet is not something we plan to nominate under any “best looks” categories.
See also: The best Korean skincare brands you can find in Canada.
