The 39 Things I’d Buy During Madewell’s Sitewide Insiders Sale

By,a deals writer at the Strategist.She was previously the Strategist's weekend and holiday writer, and she's a former editor and freelance writer at Interview and Time Out magazines
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Photo: Photo-Illustration: The Strategist; Photos: Retailer

Now through March 22, Madewell Insiders (it’s free tobecome one) can take 25 percent off most merchandise, including already-on-sale items. While Madewell’s regular sale section always has plenty to browse, the size and color options are generally sparse; the Insider Sale is one of the only times when you can get new, fully stocked styles on sale. In other words, it’s a rare opportunity to save on exactly what you’re looking for.

The sale applies toalmosteverything — just non-Madewell brands, cashmere, and selvedge denim are excluded — so there’s a lot to look through. To help you, I’ve curated a very digestible collection of what I think are the brand’s most classic, wearable, and fashionable pieces on offer for both women and men. Select from the lineup below or consider it a good jumping-off point foryour own shopping spree.

Women’s tops and outerwear

Madewell The Perfect Crewneck Tee in Allday Jersey
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$36
$45now 20% off

An no-nonsense, 100 percent cotton tee that comes in ten colors.

Madewell Crewneck Cutaway Vest in Drapey Twill
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$98

Pair this Tencel-cotton-linen-blend vest with some low-cut pants if you want to show a little skin.

Madewell Easy Crewneck Long-Sleeve Tee
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$68

I personally find the combo of slouchy fit and cobalt stripe pretty irresistible.

Madewell The Easy Shirt
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From $88

This cotton button-down comes in nine colors, including stripes.

Madewell Linen Drop-Shoulder Sweater
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$80
$118now 32% off

A lightweight, drapey linen sweater is perfect for spring.

Madewell Drop-Shoulder Sweater in Merino Wool
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From $30
$98now 69% off

A similarly drapey, drop-shoulder sweater with a ribbed waist in all-weather merino wool.

Madewell The '90s Boatneck Tee in Compact Cotton
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$55

The perfect throwback tee with a slim cut and a flattering boatneck silhouette.

Madewell The Billie Short Jacket
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$170
$218now 22% off

A classic chore coat with a modified cropped cut. The tonal blue is very chic.

Women’s bottoms

Madewell The Perfect Vintage Wide-Leg Jean
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$148

These high-waisted, wide-leg jeans have of a hint of stretch to bounce back instead of bag out.

Madewell The Flare Crop Jean in Super Stretch Denim
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$148

Jeans that combine the flattering silhouette of a kick-crop pant and the casualness of denim.

Madewell The Darted Barrel-Leg Jean
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$100
$148now 32% off

A Strategist staffer favorite, now almost half off.

Madewell Pieced Barrel-Leg Jeans
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$100
$148now 32% off

I can't say "no" to a barrel jean. These have a subtle cut, a button fly, and non-stretch denim.

Madewell The Darted Barrel-Leg Utility Pant
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$114
$128now 11% off

A utility-pant version I'm also having a hard time resisting.

Madewell Pull-On Pants in 100% Linen
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$90
$98now 8% off

These drawstring linen pants come in four colors, but I'm really drawn to this green.

Madewell The Emmy Wide-Leg Pant
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$90
$128now 30% off

The Emmy is a Madewell best seller, and this red is boldly cool. It also comes in blue.

Madewell The Zoe Relaxed Straight Pant in 100% Linen
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$105
$118now 11% off

This straight-leg pant looks somehow both pulled together and utterly comfortable.

Madewell The Perfect Vintage Mid-Length Jean Short
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$78

Not too short, not too long, and well priced. Grab them now before sizes sell out.

Women’s footwear and accessories

Madewell The Milano Fisherman Sandal
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$90
$138now 35% off

A delicate take on the classic fisherman sandal that can easily be dressed up or down.

Madewell The Mylie Ballet Flat
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From $128

The high vamp and square toe are cute, and this very on sale peachy color is perfect for spring.

Madewell The Oaklynne Sneaker
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$148

I'm usually an Onitsuka Tiger girl, but I love the low profile of these retro kicks.

Madewell The Jamie Boat Shoe in Suede
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$90
$168now 46% off

These navy-blue boat shoes are nice with the navy laces ...

Madewell Cord Boat Shoelaces
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$10

... but they look even better paired with these on-sale paracord laces.

Madewell MWL Cloudlift Ankle Socks
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$15

These socks give Le Bon Shoppe's Boyfriends a run for their money.

Madewell The Essential Bucket Tote
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From $198

A few colorways of this nicely oversize bucket tote are now under $100.

Madewell The Mini Pouch in Suede
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$158

This slouchy suede bag is perfect for going out but keeping it casual.

Madewell Medium Silk Bandana
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From $68

Everyone needs at least one nice bandanna-size scarf for accessorizing.

Men’s tops and outerwear

Madewell Men's The Vintage Tee
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From $45

Several colors of this vintage-inspired, premium-weight cotton tee are part of the sale-on-sale.

Madewell Men's The Long-Sleeve Vintage Pocket Tee
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From $40
$58now 31% off

And so is every color of the long-sleeved pocket version.

Madewell Men's Crewneck Sweatshirt in Loopback Terry
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$60
$88now 32% off

Speaking of vintage cuts, I'm loving the raglan sleeve and well-worn look of this terry crewneck.

Madewell Men's Workshirt in Cotton
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$118

This garment-dyed button-down works as an overshirt and on its own.

Madewell Men's Cotton Shaker-Stitch Crewneck Sweater
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$80
$118now 32% off

I like both the Shaker-stitch knit and the unexpected sage color of this spring-weight sweater.

Madewell Men's Hooded Officer Coat in Cotton Poplin
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$150
$348now 57% off

A hooded poplin trench you can start wearing immediately.

Men’s bottoms

Madewell The 1991 Loose Straight Jean
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$148

These straight-leg pants have a semi-loose fit and are made from rigid 100 percent cotton denim.

Madewell The Arc Pant in Denim
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$80
$148now 46% off

Basically a barrel cut for guys, so of course I'm a big fan.

Madewell The Canvas Utility Pant
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$70
$138now 49% off

Cut like a classic chino but made of non-stretch cotton canvas.

Madewell Relaxed Straight Workwear Pants
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$60
$128now 53% off

Another chino alternative, this time made from a rugged canvas with reinforced stitching.

Men’s footwear and accessories

Reebok Club C 85 Sneakers
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$80
$85now 6% off

Reebok's classic tennis sneaker done in brick-red suede.

Madewell O-Ring Leather Belt
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$60
$88now 32% off

This veg-tanned leather belt has a vintage feel and a versatile O-ring closure.

Madewell Cotton-Blend Beanie
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$48

A cotton-blend beanie you can wear even when the weather gets warmer.

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The Strategistis 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 abouthere. We update links when possible, but note that deals can expire and all prices are subject to change.

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