Sweaters, Jeans, and More Are Up to 60 Percent Off for Madewell’s Insider Sale

By,a former deals writer at the Strategist.Previously, she was a shopping writer for Refinery29.
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Photo-Illustration: The Strategist; Photos: Retailers

Madewellmakes many of our favorite wardrobe-stapletees,jeans,work pants, and more. But they can be pricey, which is why we recommend shopping on sale. Right now, there’s a particularly good sale, theInsiders Sale, going on.Everythingis 30 percent off for Madewell Insiders (it’s free to become one), and plenty of already-on-sale items have steeper double discounts. And while Madewell is more often running some kind of sale than not, this one is noteworthy because stock is good and items that almostnevergo on sale, like leather goods or new jean styles, are well discounted.

Below, I rounded up all the best deals at this month’s sale, including one staffer’s favorite slouchy jeans, a Best in Classwhite tee, and many more Strategist-backed pieces. The sale ends Monday, September 29, but I recommend shopping now, while items are well stocked. To make sure you never miss a good sale, sign up for theStrategist Sales Alertnewsletter.

Women’s fashion and accessories

Women’s tops

Madewell Softfade Cotton Boxy-Crop Tee
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Whilehunting for the perfect white tee, Mya Gelber tried this boxy-crop option from Madewell and rated it highly. It was “one of the lightest and softest tees I tried,” she says, and it had a perfect length, falling right below her waistband. She returned several of the tees she tried, but she kept this wrinkle-resistant one.

Madewell The Perfect Crewneck Tee
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Gelber also tried this less cropped mid-weight “perfect crewneck” tee — and liked it even better that the Softfade tee above. “A true classic made from 100 percent jersey cotton … it’s the kind of staple that works just as well with low-rise jeans as it does with tailored pants,” she says.

Madewell Crewneck Long-Sleeve Tee
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If you’re after fall-wardrobe basics, there are plenty to be found, like this classic ribbed long-sleeve with a back seam. It comes in baby blue and white, too.

Madewell Puff-Sleeve Button-Up Shirt
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From $60

A fall essential for the office.

Madewell Merino Wool Pullover Sweater
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I particularly like Madewell’s sweaters, but as they’re usually over $100, I only buy them on sale. A few caught my eye this season, starting with this just-fitted-enough 100 percent wool one.

Madewell SoftWool Boxy Crewneck Sweater
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This wool-blend one’s even cheaper, at over half off, and has a slightly longer, slouchier fit. It’s only available in this caramel color, though.

Madewell Striped Pullover SweaterIn Alpaca Blend
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Madewell Cashmere Button-Front Cardigan Sweater
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This is a pretty good price for cashmere, and because you can wear it unbuttoned as a cardigan or buttoned up as a sweater, you’re really getting two pieces in one.

Madewell Deep V-Neck Cardigan
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Another two-in-one piece, this one made from a lighter-weight wool-silk blend.

Women’s bottoms

Madewell The Longline Straight Jean
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We’verecommended truly dozens of pairs of Madewell jeansover the years — they’re high-quality and come in a nice range of sizes and styles. For taller women, we like the newish Longline style, which has 30-inch inseam and is almost half off right now.

Madewell The Balloon Jean
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Madewell The Balloon Jean

$100
$148now 32% off
$100

The Balloon jean was here before barrel-leg jeans reached peak popularity, and it’s still a nice option. Lots of washes available, but I’d go with this nice dark wash for fall.

Madewell Kick Out Full-Length Jeans
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But if you’re post-barrel, perhaps you’d like the flare-ish Kick Out jean. It’s as little as $56, depending on the color.

Madewell The Slouchy Straight Pant
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You can wear these to work on repeat this fall and winter.

Madewell The Easy Pull-On Pant in 100% Linen
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The season for linen is over, which makes now a great time to grab these easy pants. At just $49 (half off), they’re a great deal on linen anything.

Women’s dresses and skirts

Madewell Sleeveless Maxi Dress
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$90

Wear it with sandals, mary janes, or boots — it’s an all-seasons satin dress.

Madewell Denim V-Neck Circle Midi Dress
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The most interesting denim dress I’ve seen in a while.

Madewell Pleated Linen Mini Skirt
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At 60 percent off, this linen mini is one of the best deals on this list. It only comes in chocolate brown, but that just means you can wear it in the fall.

Outerwear

Madewell Denim Trapeze Jacket
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Dark wash, corduroy collar, swingy-loose fit. It’s a new staple jacket.

Madewell Single-Breasted Trench Coat
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A nice, simpletrenchin classic khaki for over $100 off is a very good deal indeed.

Madewell x Alpha Industries MA-1 Flight Jacket
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Pieces from Madewell’s collaboration with heritage brand Alpha Industries are included in this sale (surprisingly). I’d grab their take on a flight jacket, with a nylon shell and lining and polyester filling.

Women’s accessories

Madewell The Essential Bucket Tote
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This is one of thework totesthat caught Mya Gelber’s eye when she went on the hunt for the best ones. It fits a laptop, has the perfect strap length, and comes in a perfect brown leather. You’ll rarely find Madewell’s leather bags for such a high discount, so if you’ve been considering, now’s the time.

Madewell Alpaca-Blend Scarf
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This season’s new scarf, sorted.

Madewell The Greta Ballet Flat
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Men’s fashion and accessories

Men’s tops and jackets

Madewell Relaxed Tee
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One of our very favoritemen’s black teesis now just $28. It has a loose fit, a lived-in feel, and a “sturdy collar,” says writerBrenley Goertzen, and it looks great with a pair of blue jeans.

Madewell Cotton-Poplin Overshirt
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A light (but not too light) cotton overshirt you can layer all fall. It comes in dark brown and off-white.

Madewell Cotton Shaker-Stitch Polo
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Madewell’s sweaters are just as nice in the men’s section. This one’s great for the office.

Madewell Cotton Shaker Stitch Cardigan
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As is this one, which looks just as nice unbuttoned as it does buttoned.

Madewell Mesh-Knit Crewneck Sweater In Lightweight Cotton-Linen Blend
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Madewell Raglan-Sleeve Trench Coat
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$150

Madewell’s men’s trench is just as nice (and just as good of a deal) as it’s women’s trench.

Men’s bottoms

Madewell The 1991 Loose Straight Jean
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Just as we’ve oft-recommended Madewell’s women’s jeans, we’re big fans of itsmen’s jeans. This pair is one of Strategist associate editor Jeremy Rellosa’s favorite relaxed, wide-leg pairs (that don’t make him look like a toddler). “The jeans have a fuller leg compared to my other straight-fit jeans, but they aren’t so overly baggy or loose that they fully enter relaxed-fit territory,” he says. “I like that they also keep their structure and don’t billow like other relaxed-fit jeans might.”

Madewell The Wide-Leg Jean
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From $148

But if youdowant super-wide-leg jeans, this pair delivers.

Madewell Peated Denim Pants
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Madewell Peated Denim Pants

$70
$148now 53% off
$70

Pleated pants for the office.

Men’s accessories

Madewell Three-Pack MWL Cloudlift Crew Socks
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Three pairs of socks for $7 apiece is a good deal, and these are extra-padded for extra comfort.

Carhartt Work In Progress Tyler Bucket Hat
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Madewell Men’s Cotton Beanie
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And grab this season’s new beanie now in Madewell’s (apparent) favorite color right now — dark brown.

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