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 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 Insider 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, well, 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 oversized 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
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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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