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Mark your calendars: the Madewell Insiders Event ends September 27. Until then, Insiders get 25% off everything (well, almost everything—sadly, cashmere is excluded). Plus, get an extra 40% off sale items like these Ashley Ruched Loafers ($84).
Nearly every fashion person I know is signed up for the free Insider program to earn the benefits, i.e., 25% off the buzziest new arrivals. As a Madewell member myself (and a fashion editor looking for an affordable way to revive my fall wardrobe), I popped into my local store to try on some incredibly chic outfits, all for under $483.
I styled new-in sweaters and blouses plus fall staples like corduroy trousers and checkered flannels. I doubled down on accessories—think calf-hair zebra-print ballet flats, plaque-buckle belts, and silk scarves. I embraced the denim-on-denim trend I’ve been spotting on NYC sidewalks and chic French women lately. And I left with a few goodies to revive my closet.
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Scroll on to see the four outfits I styled and shop the best of the Madewell Insiders Event. Happy savings!
The Madewell Insiders Sale Event 2026
1. Double Denim + Plaque Buckle Belt + Glove Flats
First up: a Canadian Tuxedo. I styled the denim shacket over a ringer T-shirt, tucked it into bandana-patchwork jeans, and cinched the baggy look with a plaque-buckled belt. I always lean a little Western come September. Maybe it’s the changing leaves that causes this sudden craving for denim on denim. Whatever it is, it looks chic, and right now, it’s on discount.
Madewell
Shirt-Jacket in Airy Denim
Madewell
The Perfect Crewneck Tee in Allday Jersey
Madewell
Low-Slung Baggy Jeans
Madewell
The Greta Glove Flat
Madewell
Oval Plaque-Buckle Belt
2. T-Shirt + Crewneck Sweater + Satin Pants
It girls would approve of this look. A pop of color draped over my shoulders in the form of a 100% merino wool crewneck, a perfectly oversize white T-shirt, satin trousers with a silk scarf tied around the waist, and a touch of animal print with calf-hair zebra flats.
Madewell
The Relaxed Tee in Vintage Jersey
Madewell
The Mila Sweater in 100% Softwool
Madewell
Medium Silk Bandana
Madewell
The Mylie Ballet Flat
3. Checkered Flannel + Tan Jeans + Suede Loafers
I’ve noticed fashion people are wearing more than one button-down, either going for a double-collar look or tying one around the waist (which is what I decided on here). Whatever you choose, make sure it’s the Easy Shirt from Madewell. As the name suggests, this 100% cotton shirt is easy to style. I especially like it with the Low-Slung Baggy Jeans and Ashley Ruched Loafer.
Madewell
The Easy Shirt in Poplin
Madewell
Low-Slung Baggy Jeans
Madewell
The Ashley Ruched Loafer
Madewell
The Easy Shirt in Poplin
4. Ruffle Blouse + Corduroy Trousers + Ankle Boot
No fall outfit guide is complete without a corduroy look. The textured trousers shine when worn with a ruffled blouse and suede accents. I’m thinking of going back and picking up the Idris Ankle Boots. Oh, and don’t forget to color-match with burgundy accessories.
Madewell
The Georgina Top
Madewell
The Low-Rise Loose Pant in Corduroy
Madewell
The Lexington Crossbody Bag
Madewell
Medium Bandana in Cotton
Madewell
The Idris Ankle Boot
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