Everything at Madewell Is on Sale — Here’s What’s Worth Getting

By , a senior writer at the Strategist covering fashion. She joined the Strategist as a writer in 2021 and before that worked at NBC and HuffPost.

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Photo-Illustration: The Strategist; Photos: Retailers

A Madewell sale is always good news, but a Madewell sale on everything is even better news. This week, the brand’s Insiders sale is back, meaning 25 percent off everything full price for “Insiders” (a.k.a. those who have an account with the store — you probably already have one, but if not, it’s free to sign-up with an email), plus an extra 40 percent off the sale section. Because there are so many deals on the site right now, I shopped around for you. Some highlights: the jeans one stylist has recommended to more than 150 clients now at what might be the cheapest price I’ve seen, and the pants several Strategist staffers own at more than half-off. Plus our already affordable best-overall work bag is now even more affordable. The sale ends on September 30, so you have a few days to shop — but don’t dillydally, as pieces and sizes will sell out soon.

Tops

Madewell Split-Crewneck Cardigan Tank
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It’s a cardigan. It’s a tank. It’s a carditank.

Madewell Pointelle Long-Sleeve Scoopneck Tee
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I’m a sucker for a picot trim, especially on some pretty pointelle.

Madewell Long-Sleeve Scoopback Tee
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A combo boatneck-scoopback that’s bra-friendly.

Madewell Bouclé-Knit V-Neck Cardigan Sweater
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The ribbed, nubby knit will make you feel like a teddy bear.

Madewell Textured Cotton Crewneck Sweater
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The trimming reminds me of frosting on gingerbread houses (in a good way).

Madewell Rugby Polo Tee
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I don’t know the rules of rugby, but I do know you can sport a rugby shirt off the field.

Madewell V-Neck Long-Sleeve Top
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The most Madewell-y Madewell shirt.

Madewell Relaxed Button-Up Shirt
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You might not need another white button-down, but you do need one (at the very least) that’s striped.

Madewell Asymmetric Button-Up Shirt
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Madewell Short-Sleeve Mockneck Tee
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It’s almost Yves Klein blue.

Madewell Whisper Cotton Scoopneck Tank Top
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A version of this infinitely layerable tank was a big hit with Strategist readers on Prime Day.

Madewell x Lisa Says Gah! Embroidered Button-Front Shirt
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Bottoms

Madewell The Perfect Vintage Jean
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Madewell The Perfect Vintage Wide-Leg Jean
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The same pair — now with a wide-leg.

Madewell Kick Out Crop Jeans
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Don’t let the “crop” fool you. The jeans actually come in inseams long enough for those who are tall — and taller.

Madewell Denim Cross-Back Jumpsuit
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It’s not too E-I-E-I-O (blessedly).

Madewell Stovepipe Jeans
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I once heard someone describe the stovepipe as (in so many words) “if all jeans had a baby, this style would be it.”

Madewell Leather Midi Skirt
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It’s a splurge alright, but when are you ever going to find leather — never mind in a column skirt — at that price?

Madewell The Harlow Wide-Leg Pant
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Actress Victoria Justice first put us on to these pants. Since then, they’ve become a favorite of several Strategist staffers, including New York deputy editor Alexis Swerdloff. She says, “They truly make me feel like I’m wearing pajamas to work.”

Madewell Darted Barrel-Leg Pants
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I can’t walk a block without seeing at least one barrel-leg.

Madewell The Emmett Wide-Leg Pant in Corduroy
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I’m going to argue that corduroy pants are to fall what jean shorts are to summer.

Dresses

Madewell Sleeveless Midi Dress
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What a slinky little number!

Madewell Denim V-Neck Midi Dress
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Between you and me, I think I like this denim dress more than the Alex Chung for Madewell one (sorry!).

Madewell Button-Front Mini Shirtdress
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A shirtdress you don’t have to tie at the waist.

Madewell V-Neck Balloon-Sleeve Maxi Dress
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Madewell The Layton Midi Slip Dress
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I mean it would be wrong not to be get a dress for only $36 — especially one done in a good graphic print.

Outerwear

Madewell Belted Trench Coat in Drapey Twill
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An excellent trench with an equally excellent drape.

Madewell Button-Front Denim Jacket
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Madewell Lady Jacket in Tweed
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To channel the well-dressed ladies of Madison Avenue.

Shoes and accessories

Madewell The Grayson Penny Loafer
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These are cheaper than Weejuns right now.

Madewell The Beverley Mary Jane Flat
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Madewell The Transport Tote
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Our best-overall work bag, which can tote around a laptop, all sorts of cords, a water bottle, snacks, and more.

Madewell The Essential Bucket Tote
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And something smaller for those who carry fewer essentials.

Madewell The Sling Crossbody Bag
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Or if you truly want to feel hands-free, go for a crossbody.

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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