Up to 50 Percent Off Cotton Sweaters, Jazz Shoes, and Denim in Madewell’s Long Weekend Sale

By , the Strategist’s sleep writer, covering mattresses, pillows, and more. She has been writing about sleep products since 2021, previously as a staff writer for Sleepopolis.

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Photo-Illustration: Strategist; Photos: Retailers

Madewell is taking 30 percent off select fall styles and 30 to 50 percent off sale-on-sale pieces with the code LONGWEEKEND. There are plenty of classic and on-trend fall pieces, from jazz-shoe oxfords to 100 percent cotton sweaters. The best deals are, naturally, to be found among the sale-on-sale, though sizes and stock are much more limited than the newly on-sale items. To help you find the best deals, I dug through Madewell’s many pages of sale items to curate a collection of nice-looking, wearable pieces for fall that are in stock in most sizes. Take a look below at my selections, or head over to Madewell to browse for yourself — there’s plenty to consider!

Women’s tops and outerwear

Madewell Casey Crewneck Sweater in Merino-Silk Blend
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Madewell Pointelle-Knit Peplum Cardigan in 100% Cotton
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$110
$138 now 20% off

I like the highly textured look of this cotton cardigan.

Madewell Easy Shirt in Poplin
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$98

Here's an autumnal button-up that could work for the office or the pumpkin patch.

Madewell The '90s Envelope Tee in Compact Cotton
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$44
$55 now 20% off

The stripes and criss-cross envelope neckline make this more interesting than the average tee.

Madewell Smocked Boatneck Sleeveless Top
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Madewell Button-Front Sleeveless Cardigan
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$65
$78 now 17% off

Wear it on its own or layered with a long-sleeve tee.

Madewell Longline Cardigan Jacket
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$138

This polished cardigan is made from 85 percent merino wool.

Madewell Denim Tie-Neck Shirt
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$75
$108 now 31% off

Why not tie a jaunty little scrap of denim around your neck?

Madewell Cropped Button-Front Jacket
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$100
$158 now 37% off

I'm quite taken by this eye-catching but versatile striped jacket.

Madewell The Billie Short Jacket
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$175
$218 now 20% off

A waxed cotton-nylon blend bomber with a corduroy collar screams fall.

Madewell Billie Long Jacket
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$248

The long version is rather smart too.

Madewell Mercer Relaxed Blazer
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$248

Perfect for a cool English professor (or those aspiring for the academic vibe).

Women’s bottoms

Madewell The Perfect Vintage Wide-Leg Jean in Airy Denim
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$148

Classic blue jeans that go with all your favorite fall sweaters.

Madewell The Curvy Perfect Vintage Wide-Leg Jean
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Madewell The Darted Barrel-Leg Jean
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Madewell The Ultimate Wide-Leg Jean
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$148

I love the look of the wide cuffs on these jeans.

Madewell The Low-Rise Loose Jean
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$158

A slouchy double-knee carpenter jean.

Madewell Devon Pant
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$80
$98 now 18% off

Satin-back crêpe pull-on pants for when you want to look put together while lounging.

Madewell A-line Mini Skirt
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$90
$118 now 24% off

Pair with a sweater and boots to look festive for all your autumnal activities.

Madewell Pintucked Midi Skirt
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$110
$128 now 14% off

For fall days that feel more like late summer.

Madewell Elena Slip Skirt
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$90
$118 now 24% off

I love the earthy tones on this viscose slip skirt.

Women’s dresses

Madwell Elena Mini Dress
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$100
$148 now 33% off

The swingy minidress version is nice too.

Madewell Lace-Insert Tie-Front Midi Dress
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$120
$178 now 33% off

It's like a Salter House nightgown you can wear out of the house.

Madewell The Layton Midi Dress
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From $135
$168 now 20% off

Here's an even more discounted style with a similar feel.

Madewell Seamed Scoopneck Midi Dress
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$130
$168 now 23% off

How charming would this be with a turtleneck long-sleeve layered underneath?

Madewell Long-Sleeve Boatneck Mini Dress
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$120
$148 now 19% off

The teensy star pattern is sweet without being too cutesy.

Madewell The Chrissy Denim Mini Shirtdress
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$95
$138 now 32% off

This 100 percent cotton shirtdress would transition well from fall to early winter with tights.

Women’s footwear and accessories

Madewell Grayson Penny Loafer
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$146
$178 now 18% off

I'm on the hunt for a slip-on fall shoe and these penny loafers look like a good option.

Madewell Calli Ankle Boot
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$218

These pointed toes would look so dramatic (positive) peeking out from a wide-leg jean.

Madewell Greta Oxford
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$148

An oxford with an on-trend jazz-shoe flair.

Madewell Archival Knee-High Boot
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Madewell Sunglasses Case with Strap
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$68

The grown-up (and actually useful) version of a bag charm.

Madewell Double D-Ring Belt
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$78

An interesting but not-too-flashy leather belt.

Madewell Russell Oval Sunglasses
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$75

Nice-looking sunglasses you don't have to be too precious about.

Madewell Small Silk Bandana
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$48

Tie it around your ponytail or handbag for easy accessorizing.

Madewell The Signature Woven Bucket Bag
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$180
$228 now 21% off

And here's almost half-off a perfect everyday bag for fall.

Men’s tops and outerwear

Madewell Bouclé Cardigan
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$148

This cozy sweater is made from 89 percent wool.

Madewell Textured-Stitch Collared Cardigan in 100% Cotton
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$138

An ideal layering piece that's a little more unexpected than a flannel.

Madewell Shaker-Stitch Crewneck Sweater in 100% Cotton
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$118

A sharp-looking sweater made entirely from cotton.

Madewell Cotton Shaker-Stitch Polo
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$90
$128 now 30% off

This collared style is also 100 percent cotton.

Madewell Ribbed Crewneck Sweater
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$90
$118 now 24% off

Perfect for laidback weekends this fall and cozy evenings in the winter.

Madewell The Reissue Cord-Collar Denim Chore Jacket
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$228

A heritage-style jacket you can layer over just about anything.

Men’s bottoms

Madewell The 1991 Straight-Leg Jean in Artisan Comfort Selvedge
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$168

This ’90's-inspired style is made from 99 percent cotton and one percent elastane.

Madewell Athletic Slim Jeans
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$148

A slightly tapered fit that's not quite in skinny-jeans territory.

Madewell Relaxed Taper Jeans in Summerweight Denim
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$148

These relaxed-fit jeans are made from a blend of cotton and hemp for a lightweight feel.

Madewell Relaxed Taper Jeans in Comfort Selvedge
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$168

Some will tell you not to wear white after Labor Day, but technically these are ecru.

Madewell Utility Pant in Poplin
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$89
$138 now 36% off

Here's an easy-to-wear pair of garment-dyed cotton poplin pants.

Madewell Pull-On Pant in Linen
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$90
$138 now 35% off

With an elastic waistband and internal drawstring, these are essentially secret sweatpants.

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The Strategist is designed to surface useful, expert recommendations for things to buy across the vast e-commerce landscape. Every product is independently selected by our team of editors, whom you can read about here. We update links when possible, but note that deals can expire and all prices are subject to change.

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