Madewell’s Insider Sale Is Still *Loaded* With Sweaters, Boots, and Other Fall Wardrobe Staples Up to 40% Off

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It’s spooky season. Cozy sweater season. Leaf peeping season? Whatever you call it, autumn is officially here and that means we’re packing away our bikinis and cover-ups and adding some fresh ‘fits to *pumpkin spice* up our wardrobes. Our first stop? Madewell, which has a cornucopia of cozy must-haves up to 40 percent off through next Monday.

Twice a year, Madewell throws an extra special sale for its Insiders, aka, members of the brand's email rewards program who get exclusive perks year-round. It's free to sign up, however, your "status" determines how big of a discount you get during the Madewell Insider Event: Entry-level Insiders can save up to 25 percent off seasonal styles, while Star and Icon tiers (those who spend $500+ or $1000+, respectively) can save up to 30 percent off. And all Insiders, regardless of spending habits, can score 40 percent off sweaters at check out. Now that's a deal we're fall-ing for...

And you know how, around the beginning of fall, most retailers try to offload their summer stock, all breezy sundresses and swimsuits? Not here. Madewell has plenty of knits, boots, beloved jeans, and coats to get you perfectly prepared for the shorter days and chillier nights.

Whatever you call the fall, it's here—make sure your closet is ready for it. Stock up on autumnal essentials at the Madewell Insiders sale, running now through September 26. You don’t need to be an Insider to shop, but you’ll enjoy more unbe-leaf-able deals if you are.

8 seasonal styles you won't want to go through fall without

Seersucker Wrap Mini Dress — $86.00

Originally $128, now $86 for Insiders

Be still, my apple-picking heart. This dress was absolutely made for fall foliage, when the temps aren’t quite crispy enough for the full on *sweater weather aesthetic*, but you’re hoping to get a lil’ autumn festivity going. Layer with tights, boots, and a coat for an ultra-cute cold-weather look, or relish the last of the sunshine by wearing it as is.

Available sizes: XXS-XXL in standard, petite, and plus sizes.

Zip-Front Cropped Coverall Jumpsuit — $107.00

Originally $148, now $107 for Insiders

Trust us: a go-to jumpsuit is the BFF your closet deserves. Business casual? Done. Day at the farmer’s market? Done. Lounging around the house? Oh baby. Having a staple item you can dress up and down for any occasion is worth the investment — and definitely worth the buy when it’s on sale. Madewell’s zip-front version sports 100 percent cotton non-stretch denim with a baggy tapered leg and long raglan sleeves you’ll want to live in for months.

Available sizes: XS-XXL

Mayfair Sweater Cardigan — $71.00

Originally $95, now $71 for Insiders

If you are a sweater weather diehard, add this comfortable (40 percent off!) cardigan to your shopping cart. Its slightly boxy, baggy fit makes it an ideal layering staple you can wear over henleys, T-shirts, tanks, and more. The super-soft yarn doesn’t hurt either, nor do the seasonal colors that are neutral enough to go with everything: warm gold, dusty blush, olive green, and crisp cream.

Available sizes: XXS-XXL in standard and plus sizes.

The Perfect Vintage Flare in Sherborn Wash — $75.00

Originally $100, now $75 for Insiders

Everyone needs a go-to pair of black jeans. They’re effortless, stylish, and the right pair just makes you feel really good. In keeping with the bootcut trend that’s back for Fall 2022, this Perfect Vintage Flare Jean is in fact, perfectly vintage. A high-waist cut hits just below the belly button (sorry, low-rise), looking chic with cropped tops and longer tunics alike.

Available sizes: 23-33 in standard, plus, petite, and tall lengths.

Re(Sourced) Fleece Button-Front Hoodie Sweatshirt — $82.00

Originally $110, now $82 for Insiders

We’re suckers for a fluffy fleece. It’s the piece you’ll reach for again and again when you shiver. Contrasting corduroy details add just the right bit of edge, while the comfy, touchable texture will make you feel bundled up wherever you are. Bonus points for the rich burgundy color and the recycled construction—made from 100% post consumer waste that would otherwise end up in landfills.

Available sizes: XXS-XXL

The Cecily Clog in Oiled Leather, English Saddle — $105.00

Originally $143, now $105 for Insiders

In case ya missed it, clogs are en vogue in a major way this autumn, but honestly, we just love clomping around in them, trendy or not. The oiled leather makes the shoe ~fancy~ enough to wear to a work function, date, or nicer event, while the MWL Cloudlift Lite padding makes for cushy stride.

Available sizes: Women’s 5-11 in half sizes.


Knit Corduroy Redford Blazer — $71.00

Originally $95, now $71 for Insiders

Blazers may be the epitome of sleek chic, but corduroy has a relaxed warmth that’s totally made for seasonal dressing. This Madewell combo brings the best of both worlds that’s def making it to every Zoom call we take for the next three months (at least.) Its cozy construction and slouchy fit is also perfect for chillier days when you just want to feel snug. Choose from rich brown hazelnut or sun-faded indigo reminiscent of an October dusk.

Available sizes: XXS-XXL



Lace-Up Lugsole Rain Boot — $66.00

Originally $88, now $66 for Insiders

Before we get to snow season, we’re gonna get a lil’ bit of drizzle. While we might be okay just, erm, drying out our sneakers in the summertime, wet feet are no fun when the temps plummet. Enter The Lace-Up Lugsole Rain Boot, the ideal rugged-ish pick that’ll keep you warm and dry no matter the weather. One reviewer based in the Pacific Northwest calls these, “the most comfortable rain boots I own.”

Available sizes: Women’s 5-11

Shop the rest of the Madewell sale here. 

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Our editors independently select these products. Making a purchase through our links may earn Well+Good a commission.

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