Madewell’s Sitewide Sale Just Got Better. Here’s What to Buy.
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Madewellmakes many of our favorite wardrobe staples — likejeans,work bags,work pants, andflats. And while you can often find select items on sale, there are only a few times a yeareverythingat the brand is discounted. Right now, the Madewell Insider Event is one of those times. We’re halfway through the sale, and while the entire site is still 25 percent off for Madewell Insiders (it’s free to become one), already-on-saleitems are now an extra 40 percent off. It’s a good time to get items that rarely go on sale, like shoes and bags, but it’s also a good time to score an extra-deep discount on any clearance winter styles you’ve been eyeing.
Below, I’ve rounded up all my top picks from the sale, grouped by gender and category. I’ve included any products we stand behind, like our favoriterelaxed-fit jeans for menand a pair ofmary jane flats akin to socks, but I also perused the new arrivals and called out a few favorites. The sale runs through March 23, but sizes will sell out fast, so shop sooner than later.
Women’s fashion and accessories
Women’s tops
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The dark wash and white stitching on this lightweight linen top remind me of my favorite denim jeans.
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It’s nearly boatneck-tank season. This now-$20 one has flattering, ever-so-sexy side slits.
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Our best vintage-inspiredblack teeis now under $20. Fashion and e-commerce editor Megan McCarty says it’s “easy to wear, easy to clean, and easy to layer,” and its rich black color hasn’t budged after multiple washes.
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Madewell’s Softfade cotton tee is one of the softest shirts Strategist writer Mya Gelber tried on herhunt for the perfect white tee.
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Of all the new arrivals at Madewell, I particularly like this versatile and laid-back top.
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I’m a sucker for color-blocking and, therefore, this oversize button-up. It’s made from 100 percent cotton poplin, so it’ll work in warmer weather, too.
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An airy balloon top that’s actually flattering. It’s $66 in most colors, but if you want something bright, it’s just $42 in a nice marigold-yellow shade.
Women’s bottoms
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Senior writerLiza Corsillorecentlytried on all the jeans at Madewelland said this pair “fit me really well and made me look zipped up and pulled together.”
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Thejeans a stylist recommends to all of her clients, now in a wide-leg crop style (which happens to be our favorite pair ofplus-size jeansandjeans for tall women).
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Madewell Kick Out Full-Length Jeans
As someone who’s five-foot-eight, the 32-inch inseam on these is music to my ears. Price and sizing vary by color, so be sure to check out all the options.
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Strategist managing editorKelsie Schradersays she wears her Emmett jeans no less than twice a week because they’re comfy and work well with nearly any kind of top.
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Two Strategist staffers already purchased the garment-dyed version of one of our favoritejeans for petite women. It’s the first time they’ve gone on sale since they came out.
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Sadly, the standardHarlows — one of our favorite pairs ofwork pants— are nearly sold out, but this Drapey Twill version is still available in most colors and sizes.
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A reliable pair of shorts to wear all summer.
Women’s skirts and dresses
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I don’t even wear skirts, but at $60, this classic satin maxi slip is making me think twice.
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A simple sculpted square-neck midi for your summer rotation.
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This adorable minidress is also available in black, but this green shade is my favorite.
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Thebubble hemdominated 2024, and it’s still going strong in 2025.
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For when your go-to denim skirt needs a break.
Women’s outerwear
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A comfortable, all-season jacket that you can wear by itself in the spring or layer in the fall.
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Madewell’s leather rarely goes on sale. My pick: this luxe, oversize leather blazer.
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The opposite of a tight, restrictive jean jacket.
Women’s shoes and accessories
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Flexible leather plus cushy padding equals an excellentballet flat. Content creator Ella McFadin says these flats are so comfy, they “feel like socks on your feet.”
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This suede belt’s metal hardware stands out but still complements a wide range of outfits.
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A nice, simple, slightly-dress-up summer shoe.
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Madewell The Essential Bucket Tote
If you’re looking for a replacement for the now-discontinuedTransport Tote, the Essential Bucket Tote is the next-best thing (and afavorite of Mya Gelber). It can hold a 15-inch laptop, and the long strap is the perfect length.
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Theshoulder-bag versionof this handwoven tote was immediately popular and has already sold out in almost every color. But you can still get it in every color in this larger tote size.
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A shoulder bag that can actually hold all your essentials.
Men’s fashion and accessories
Men’s tops
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Madewell Brushed Easy-Shirt Jacket
A light layer that pairs well with your favorite hoodie.
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Men’s styles rarely seem to be on sale at Madewell (and when they are, sizing is limited), so right now is really the best time to shop. If you just want to replenish your T-shirt collection, go with ourbest-in-class less-expensive mid-weight tee, which is now 40 percent off.
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There are plenty of dressier men’s shirts in the sales bin, too. I particularly like this classic camp-collar shirt, which comes in three striped patterns.
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Made of cashmere and wool and now over half off.
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Strategist associate editor Jeremy Rellosarecently bought this hoodieand says he’s already worn it too many times to count. He says it’s “soft and not too heavy or thick, but not so light that it doesn’t insulate.”
Men’s bottoms
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The only pair ofrelaxed-fit jeansthat won’t make you look like a toddler.
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If you prefer a tighter fit, the 1991s are also available in a tapered straight-leg style.
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A very versatile pair of trousers from Madewell’s “Milled in Italy” collection.
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Comfy enough to wear, truly, everywhere.
Men’s outerwear
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A simple denim jacket for your spring rotation.
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For men in search of a transitional weather staple.
Men’s accessories
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A durable leather belt to replace all your other belts.
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A neutral pack of cushioned socks, now less than $9 each.
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’Tisn’t the season, but ’tis a very good deal on a simple beanie.
The Strategistis designed to surface the most useful, expert recommendations for things to buy across the vast e-commerce landscape. Some of our latest conquests include the bestacne treatments,rolling luggage,pillows for side sleepers,natural anxiety remedies, andbath towels. We update links when possible, but note that deals can expire and all prices are subject to change.
