Everything I’d Buy During Madewell’s Insiders Event
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The Madewell Insiders Event happens twice a year, and one of those times is now: Through September 27, anyone with Insider status (which you get for free by signing up here) can take 25 percent off nearly everything sitewide. Plus, already-discounted items arean extra 40 percent off. If you’ve ever shopped the brand’s regular sale section, you know the size and color options are typically quite sparse, so the Insiders Event is a rare opportunity to save on exactly what you’re looking for. And since there’s almost too much good stuff to sift through right now, I’ve curated mini-collections of the best buys for both women and men. If you don’t find what you’re looking for in my lineup below, not to worry — there’s literally so much more to pick from.
As always, make sure to sign up for the Strategist Deal Freaks Daily newsletter to receive each day’s best deals in your inbox (as well as sales just for newsletter subscribers).
Deals I personally think are the best
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I’m a sucker for a good chore coat. This one is perfect for fall and looks just oversize enough.
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Under-$100, all-suede shoes in pretty chocolate brown (that’s maybe even better than black).
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It’s a men’s sweater, but I will absolutely be stealing it from my husband’s closet.
Women’s clothing
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It is a summer-weight top but will also look very cute under a light fall jacket.
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This comfy 100 percent cotton tee comes in so many colors.
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I’m really into the cerulean-heavy stripe on this slouchy polo.
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The perfect top half for a Canadian tuxedo.
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Keeping it zipped turns this sweatshirt into an of-the-moment mock-neck.
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I love a Shaker-stitch sweater — and this one comes in a nice fall stripe.
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This slouchy-chic 100 percent wool sweater has a nice reverse-seam detail on the shoulders.
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The hold-you-in structure of rigid jeans with just a hint of stretch for comfort.
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Strategist staffers are big fans of Madewell’s barrel-leg jeans.
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A near-perfect replica of the vintage fatigue cargo pants I’ve been looking for.
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These best-selling pull-on pants come in a range of colors, prints, and fabrics.
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Obsessed with the gorgeous ochre color of this satin maxi.
Women’s shoes and accessories
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Not too big, not too small, not too stiff, not too slouchy ... just right.
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You’re allowed to use this heavyweight canvas weekender on weekdays too.
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Wear these dainty flippies for the last blast of summer 2026 and then all of summer 2027.
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A perfectly minimalist glove shoe in a lovely and very fall-appropriate chocolate brown.
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Skimpy all-leather oxfords. I also really like a touch of white for fall.
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I also love a loden-green shoe, and the suede upper on this pair is really calling my name.
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These little 14k-plated huggie hoops have a sweet and subtle crystal detail.
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Even if you prefer to dress in more muted tones, it’s always nice to add a little hint of color.
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I’ve been on a bandanna kick lately. This one comes in many patterns, but I really love this grid.
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The not-extreme oval shape makes these sunglasses universally wearable.
Men’s clothing
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This easy cotton jersey shirt comes in more than ten colors.
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A thick cotton rugby that’s perfect for fall.
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I love a Shaker-stitch sweater — the slouchier the better.
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If you want a little interest, the stripe on this wool sweater keeps it from being too basic.
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There’s no such thing as too many really good sweatshirts. Here’s another for your collection.
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Another perfect fall chore coat, this one for the boys.
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A simple canvas jacket, but the tonal corduroy collar gives it a little twist.
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These easy-wearing poplin pants are already on sale in a two colors, so the discount is even bigger.
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These 100 percent cotton canvas pants are garment-dyed for a lived-in feel.
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These pants have the same material and comfortable fit of a French workwear jacket.
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Baggy cargos because you can be comfortable in something other than sweatpants.
Men’s shoes and accessories
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The perfect sunglasses to wear while bopping around Italy on a Vespa.
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A simple, under-the-radar pair with a midcentury vibe.
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These socks come in eight colors (the pair in light heather grey is even cheaper)
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