The Simple-Meets-Cool Fall Outfits You Can Buy Now And Wear For Years

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In this era of shopping, most of the fashion purchases we’re making are closet staples that are practical and hold longevity rather than investing in fleeting trends. I’m all for a good statement piece, but buying a piece that you can imagine yourself wearing not only now, but for seasons beyond makes the ounce of guilt you feel from the purchase instantly disappear. Plus, filling your wardrobe with versatile yet cute pieces helps you build more outfit options with less effort.

Don't worry, the simple yet cool fall outfits we're suggesting ahead are not only filled with basics and closet staples but also forward-feeling seasonal items that any fall wardrobe will benefit from. In other words, the outfit combinations ahead are styled so well, they won’t look like an outfit you put together in 5 minutes (even if you did). And thanks to our very own Who What Wear Collection at Target, the picks ahead are affordable, too. You're welcome. 

As the headline suggests, we have a handful of simple yet cool outfit options for you ahead thanks to the stunning new Who What Wear Collection pieces currently available at Target. From versatile blazers with relaxed jeans to printed sweaters with coordinating skirts, keep scrolling for the outfit ideas worth sporting this season and why. 

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(Image credit: @alyssainthecity)

If matching suits aren’t your thing, pair the plaid blazer with a relaxed pair of jeans for an L.A. girl vibe.

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Throw on an oversized cardigan to your leather pants for an ultimate cool yet cozy ensemble.

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A leather skirt is the ultimate fall essential. I love how all black looks with leather because it adds an instant edgier touch. 

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Croc and leather are two things that in my book, will never go out of style. Pair the two together and you have an outfit winner. 

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(Image credit: @whowhatwearcollection)

Houndstooth is a timeless print. End of story. 

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(Image credit: @taylranne)

A matching set can do no wrong. By wearing both pieces together, it’s an easy 5-minute outfit that looks polished as ever.

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(Image credit: @kasalaholdsclaw)

I love an all-black look, but something I love about this is the difference in textures with the corduroy. It keeps the outfit sleek, yet with a little flair. 

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(Image credit: @scarletkent)

As I said, croc is very versatile. To make a trendier ensemble, add a colored knit to the mix. 

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If you haven’t noticed, matching sets make for the easiest yet put-together outfits in the game.

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(Image credit: @jenniferatilemile)

While the prints may not be identical, they clash in all the right ways. 

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Associate Fashion Editor
Yusra Siddiqui is an editor who resides in New Jersey but bounces between the suburbs and NYC. (She's a Jersey girl at heart.) After interning at Who What Wear in 2019, she found her way to the team after graduating from LIM College in 2022 with a fashion media degree. She's also spent time writing and working for publications such as Fashionista, Coveteur, and Nylon, but she always knew that Who What Wear was where she was meant to be. When she's on the job, she's perusing runway shows, analyzing the latest thing fellow Gen Zers are up to on the internet, and sharing what she can about the modest-fashion market. You can also catch her dabbling in entertainment, talking about the costume choices of the latest Netflix series or diving deeper into how the plotline affects the viewers in a myriad of ways. Lastly, she likes to create content for Who What Wear's TikTok. Her personal time is spent doing similar but also different things—deep diving into almost every new TV show (Bridgerton, Gilmore Girls, and Stranger Things are favorites), planning her next local getaway (whenever that may be), and reading the latest Emily Henry or Sally Rooney novel in one sitting.