7 Fall-Fashion "Mistakes" Celebs Make (But They All Work)

Before we jump in, let's remember that you should always (repeat: always) wear whatever you love and feel confident in—despite any fashion "rules" out there. On that note, celebrities seem to be particularly on board with this philosophy. Whether they're stepping out in their off-duty life or on the red carpet, they simply wear what works best for them. And that's that.
For those casual fall outfits specifically, there are actually seven fashion "mistakes" A-listers such as Kendall Jenner, Joan Smalls, and Gigi Hadid seem to disregard completely. But naturally, they all totally work in their own way. Keep scrolling to check out the fall-fashion "don'ts" celebs are ignoring, and shop their key autumn essentials if you're looking to push the sartorial boundaries a bit as well.
On Priyanka Chopra: Max Mara coat; Nili Lotan sweater; Lorod skirt; Pierre Hardy boots; Louis Vuitton bag
Going the matchy-matchy route used to be a big "don't" in the fashion book, but the monochromatic vibe is actually quite forward. This fall, step it up a notch with big and bold colors like the red tones here.
Shop a skirt-and–ankle boot combo:
On Kendall Jenner: Dr. Martens 1461 Patent Oxfords ($109); By Far Rachel Bag ($365); Linda Farrow sunglasses
Socks are a funny thing. You might not think much about them, but they can make or break your outfit. Typically, the no-show sock look or a longer crew style would fit best here for a cool silhouette, but Jenner proves that a peek of a white athletic sock can actually feel quite forward and unique.
Shop cool shoes and socks:
On Victoria Beckham: Victoria Beckham Cotton Trench Coat ($910), Satin Camisole ($338), and Skinny Flat-Front Trousers ($750); Celine sunglasses
Sure, you might see the all-black look a lot, but many view it as a "safe" or "boring" choice. That said, Beckham proves that if you play with texture and fabric and choose sophisticated separates (sleek outerwear, pumps, and the like), the vibe more than works.
Shop black must-haves:
On Hailey Bieber: Jacquemus suit; Off-White Nike Air Force 1 sneakers; Celine sunglasses
Yes, tailoring is typically ideal for a streamlined and balanced suiting vibe, but the oversize, baggy silhouette is actually where it's at this season. We love how Bieber took it one step further here and opted for unexpected sneakers with her suit rather than standard heels.
Shop suiting and sneakers:
On Gigi Hadid: Gigi Hadid x Vogue Eyewear sunglasses
When you think about the best shoes to wear with leggings, sneakers, ankle boots, and slides probably come to mind first. Well, as Hadid is showcasing here, pushing the boundaries and going for an out-there style like cowboy boots is the way to go because they bring an of-the-moment spin to classic leggings.
Shop leggings and cowboy boots:
On Joan Smalls: Karl Lagerfeld sweatshirt; Alexander Wang Lyndon Combat Boots ($850)
Sweats and sneakers go together like peanut butter and jelly. But casual pants and statement moto boots is an athleisure combo you don't tend to spot as much. However, if you take a cue from Smalls here, the look is ideal for those days when you want to come across as laid-back with loose pants and a crew-neck but still fashion-forward with cool boots and other accessories.
Shop casual pants and boots:
On Katie Holmes: Chanel bag; Gianvito Rossi boots
Typically, blazers are left either undone or with just the top button buttoned. But if you want your favorite blazer to feel fresh for 2019, try buttoning all the buttons to make it feel like an alternative to a top as Holmes did here.
Shop sleek blazers:
Next, check out the shoe trends celebrities over 30 refuse to wear.

Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent 10 years at Who What Wear, currently leading the market team to deliver highly covetable and convertible content. He creates data-driven shopping guides featuring top retailers like Nordstrom, Shopbop, and Net-a-Porter and is at the forefront of Who What Wear's shopping tentpole strategies, including Amazon Prime Day. He also works on branded content initiatives and appears on camera in video and shopping livestream franchises.
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