7 Celebs Who Are Not Playing It Safe This Fall

While there are tons of classic outfit combos one could wear to easily impress this season—in fact, you can see and shop nine of my favorites here—a handful of our favorite celebs have chosen the riskier route to fall fashion and caught my attention in doing so. Whether it’s the seemingly popular decision to skip pants or the equally prevalent choice to opt for a bra instead of a blouse, from Gigi to Katie to Barbie, the below It girls are not playing it safe in the slightest, but, wow, is it paying off. 

If this is the part where you start to assume these looks won’t be for you, trust me when I say that somehow, they’re actually quite approachable. I typically describe my day-to-day style as simple, but I think I’m drawn to the below looks because, for the most part, they’re actually all twists on basics and classic pieces. To see all seven of the outfits for yourself and shop some of the items you’ll need to get the looks along the way, just keep scrolling.

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Hailey Bieber
(Image credit: Splash News)

Why bother with pants when you can look this good in an oversize leather blazer, T-shirt, and It boots? 

On Hailey Bieber: Celine sunglasses; Jennifer Fisher Maeve Hoops ($750); J Brand Elsa Birthday Blazer ($1298); MM6 Maison Margiela Inside Out Logo T-Shirt ($225); Jacquemus Les Bottes Pantalon Leather Boots ($1279)

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Joan Smalls
(Image credit: Ricky Vigil M/GC Images)

Joan Smalls took the houndstooth trend to the next level by opting to mismatch her Area bra top and pants, and I'm taking notes.

On Joan Smalls: Area Houndstooth Virgin Wool-Blend Bra Top ($550) and Crystal-Embellished Houndstooth Wool-Blend Pants ($1050)

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Bella Hadid
(Image credit: Pierre Suu/GC Images)

I'm living for the way Bella's Fenty blazer gives the illusion of a three-piece suit but with a lingerie-inspired twist thanks to the built-in corset detail.

On Bella Hadid: Ashley Zhang Small Herringbone Necklace ($500); Fenty Pinstripe Jacket with Corset ($1100) and Skinny Pinstripe Pants ($550); Gianvito Rossi Kylie Plexi Slingback Pumps ($507) 

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Rihanna
(Image credit: Splash News)

Another "daring" look I'm itching to copy is Rihanna's cardigan-and-mules outfit which, naturally, she wore to the airport, of all places, last month.

On Rihanna: Miu Miu Camouflage-Intarsia Cardigan ($780) and Wool Shorts ($595); Louis Vuitton Multi Pouchette ($1640); Bottega Veneta Padded Sandals ($790)

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Katie Holmes
(Image credit: BrosNYC / BACKGRID)

Katie Holmes schooled us in another way to turn the classic cardigan on its head when she styled hers with a matching bra top and the look went absolutely viral

On Katie Holmes: Westward Leaning Moore 03 Sunglasses ($235); Khaite The Eda Bralette ($520) and The Scarlet Cardigan ($1540); 3.1 Phillip Lim Alix Shoulder Bag ($895); Acne Studios Bernelle Leather Mules ($480)

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Barbie Ferreira
(Image credit: Rochelle Brodin/WireImage)

In more pantsless news, Barbie Ferreira took on not one but two It items for fall in a look I'll be re-creating this weekend. 

On Barbie Ferreira: Miista Carlota Mahogany Croc Leather Boots ($435)

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Gigi Hadid
(Image credit: Ricky Vigil M/GC Images)

Last but certainly not least, Gigi reminds us that the coolest (and conveniently most cost-effective) way to style a suit for a night out is simply with a bra.

On Gigi Hadid: Ralph Lauren jacket and pants

Up next: 11 fall trends you can get on Amazon, Nordstrom, and H&M.

Nicole Akhtarzad Eshaghpour
Senior Market Editor

Since starting as an intern back in 2013, Nicole Akhtarzad Eshaghpour has held several roles here at Who What Wear, and she is currently senior market editor. It was a less expected route, seeing as she was graduating from business school at USC when this all began, but it has turned out to be the best one for her. Fast-forward to 2020, and she's moved to NYC from her hometown of Beverly Hills and spends her workdays a little differently from when she was an intern starting out. Currently, she focuses on a weekly mélange of shopping content. As far as her personal style goes, she's largely drawn to classic pieces and neutral basics but will always make an exception for something colorful, printed, or bejeweled as long as it's deemed worthy enough. After all, the only thing she loves more than a good party is dressing up for one. On weekdays, she can usually be found at home eating something delicious for dinner and trying to force her husband to watch 90 Day Fiancé.