"Wait, That's Madewell?" Is All You'll Hear When You Wear These 10/10 Outfits

Honestly, it's been a while since I've taken an in-depth look at Madewell's arrivals. It wasn't till I tried on a stellar pair of trousers in-store last week (The Harlow Wide-Leg Pant) and decided I was missing out. J.Crew's sister brand is known for its denim and reliable basics, but this season's collection is chock-full of effortless and chic pieces that can be worn in a variety of ways. Aside from the usual denim and T-shirts that I've always loved at Madewell, I found cashmere sweaters, metallic accessories, and shoes that were both practical and on-trend. To prove how versatile these pieces really can be, I put together seven fall outfits that'll earn you the "best dressed" title this season. Everyone will be shocked to find out they're from Madewell and that you didn't pay thousands of dollars for the new look.

While you'll find outfits that feel very fresh and up to the 2023 standards, the looks have a curated balance to also include wardrobe staples that you'll keep for years to come. Don't sleep on Madewell like I did, and keep scrolling for more.

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(Image credit: Courtesy of Madewell)

An all-white look paired with black accessories instantly makes an outfit look more expensive than it already is. To make things even better, silver jewelry is a plus, and I was shocked to find such a luxe-looking cuff hidden in the pages of the jewelry section.

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(Image credit: Courtesy of Madewell)

When in doubt, an all-black outfit is stylish and versatile. If you have yet to find a staple leather jacket to rely on, consider this Madewell option for your wardrobe. It takes this delicate summer dress straight into fall with a little bit of edge.

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(Image credit: Courtesy of Madewell)

Just because you want a cozy day doesn't mean you have to sacrifice style, and Madewell recognizes that. These neutral-themed Asics sneakers will go with so much in your fall wardrobe but are a great pairing to this gray sweat set and trench coat.

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(Image credit: Courtesy of Madewell)

The Harlow trousers aren't the only stellar pair Madewell has to offer. This espresso pair caught my eye immediately, and I couldn't help but be in awe of how well it looked with this gray cashmere sweater. The matching hues on the New Balances simply tie the whole look together.

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(Image credit: Courtesy of Madewell)

If you still haven't gotten yourself a denim skirt, you're in luck because Madewell has this perfect under-$100 option. I love how it's styled on the model with a T-shirt and sandals, but I think it looks even better with this Western-style belt and Mary Jane flats.

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(Image credit: Courtesy of Madewell)

While a black blazer, jeans, and a white T-shirt make for a classic office ensemble, you can take things up a notch with silver loafers. They make enough of a statement, but simple silver hoops won't take any attention away from them and will complement the look.

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(Image credit: Courtesy of Madewell)

Until it gets very cold, you can continue to wear your denim shorts into the fall as long as you style them with tall boots like this.

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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.