Over the years, Madewell has been one of my go-tos for basics like T-shirts and denim pieces. The brand has had a chic revamp with major '90s vibes, and I am now fully invested in everything it has to offer this season. No, really—I want pretty much every last sweater, skirt, top, dress, pair of jeans… You name it. Don't even get me started on the leather jackets and boot selection.
While exploring the Madewell site, I came across four inspiring denim outfit ideas that I can't wait to re-create for fall. Each ensemble is the perfect mix of elevated and cool that somehow manages to appeal to a variety of personal styles. It's all in how you mix and match the pieces. Keep scrolling to check out each outfit idea, plus 31 picks I have my eye on this season. It was incredibly hard to narrow them down. And before you check out make sure to take a peek at our Madewell promo codes for more savings.
1.
Love the green.
Little black tee.
Belts are having a moment.
Great jeans no matter the season.
Sleek booties.
2.
Super-chic sunglasses.
Quick! This top is selling out fast.
It's sweater season.
This bag looks designer.
I love white jeans for fall and winter.
3.
Hello, perfect white T-shirt.
Obsessed with this black-and-gold belt.
This denim skirt is an editor favorite.
Super-chic knee-high boots.
4.
A black leather jacket is always a good idea.
Cozy and cool.
The styling options are endless.
More Chic Madewell Pieces to Shop Now
I live for a great button-down shirt.
The leather jacket is the epitome of cool.
Elevated Mary Jane flats.
Another cool denim skirt.
Bomber jackets are a big fall trend.
For the miniskirt lovers.
A coat to wear forever.
Flared denim I can get on board with.
Stripes always.
A modern take on the classic trench.
These are the coolest earrings.
Sheer details for the win.
Nineties-minimalism vibes.
Perfectly polished.
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Everything I Would (and Wouldn't) Wear to the Nutcracker Ballet as a New YorkerCosigned by former ballerinas and fashion editors.
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5 All-Black Winter Outfits That Are the Antithesis of BasicAnd so elegant.
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5 Fall and Winter Trends I'm Plagiarizing From Lucy Williams, Aimee Song, and Camille CharrièreWhich one is more your vibe?
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I've Had My Eye on These Madewell Pieces for Months—and Now They're Majorly Reduced for Cyber MondayUp to 40% off.
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If Chic Jeans-and-Boots Outfits Are the Goal, Don't Miss These Standout Picks From Zara, Madewell, and NordstromBring on a stylish fall-and-winter closet.
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Spotted in Italy: The 2026 Way to Wear a CoatZoë Kravitz gets the credit.
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If Ashley Olsen Is Your Style Aesthetic, This Is the Jacket to Wear This WinterShop the edit.
