Madewell’s Sale-on-Sale Has Winter Apparel Up to 72% Off — Here’s What a Former Employee Is Eyeing

Long weekends are good for two things: catching up on sleep and shopping. Because for whatever reason, our favorite brands have decided that three-day weekends and blowout sales go hand in hand, which I’m definitely not complaining about. 

There are hundreds of sales happening this weekend, including deals on designer handbags and shopper-loved leggings, but few are as good as Madewell’s double-discount sale, where already-discounted items are now up to 72 percent off with the code NEWYEAR. And as a former employee turned obsessee, you know I couldn’t resist adding a few things to my cart.

Of the 1,600+ sale items, these are the 10 I’m eyeing while they’re an extra 40 percent off, including a shopper-loved cashmere sweater, $15 basic every winter wardrobe needs, and leather ankle boots.

• Brightside Finerib Cropped Turtleneck, $15 with code NEWYEAR (Originally $42)
• The Layton Midi Slip Skirt, $29 with code NEWYEAR (Originally $98)
• V-Neck Relaxed Cardigan, $51 with code NEWYEAR (Originally $98)
• (Re)sponsible Cashmere V-Neck Sweater, $54 with code NEWYEAR (Originally $138)
• Square-Neck Midi Dress, $54 with code NEWYEAR (Originally $118)
• The Perfect Vintage Jean, $60 with code NEWYEAR (Originally $128)
• The Puff Crossbody Bag, $64 with code NEWYEAR (Originally $128)
• Denim Quilted Workwear Jacket, $60 with code NEWYEAR (Originally $218)
• Superwide-Leg Jeans, $70 with code NEWYEAR (Originally $138)
• The Darcy Ankle Boot, $90 with code NEWYEAR (Originally $198)

(Re)sponsible Cashmere V-Neck Sweater

If there’s one thing you buy from the sale-on-sale, make it this now-61 percent off cashmere sweater. As someone who once worked at Madewell, I’m quick to take advantage of cashmere deals because I know how rare they are. But aside from it being a great deal, the cashmere wool is seriously buttery — like so soft, I buy it even when it’s not discounted. “[The] cashmere quality is excellent,” gushed one fan of the sweater, adding that, “it is soft and lightweight.” Others deemed it a “great winter staple,” explaining that it’s “super soft and warm,” while one person wrote, “It is truly a perfect sweater…[it’s] very flattering and not too short.” Plus, this brick red color is beyond stunning.

The Perfect Vintage Jean

The Perfect Vintage Jean is a forever love of mine because of how flattering and timeless the style is. This style tapers ever so slightly at the bottom — a must for those on the shorter side who are looking to add a little length to their legs — and is made from a structured but not rigid cotton and elastane blend. “These are one of my favorite Madewell jeans,” one shopper wrote, explaining that the style is “fitted in the waist and hips” with a “straight leg [that] makes them much [more] modern than a skinny pair.” Plus, they’re “super flattering.” According to one person who wanted to update their “outdated skinnies” but wasn’t quite ready for a super wide leg, these are the perfect compromise, adding that they have a “perfect tailored look.” 

Brightside Finerib Cropped Turtleneck

I can almost always rationalize spending $15, but when it’s on a closet staple I’ll wear over and over again, I don’t really even have to think twice. The brand’s Brightside Finerib Cropped Turtleneck is simple but elegant, with everyone from Meghan Markle and Katie Holmes wearing the timeless style. Madewell’s fitted turtleneck is a favorite among shoppers for its “super flattering” fit and light weight that makes it “great for layering or wearing alone.” According to someone else, this is “an essential staple” in any winter wardrobe because of how well it “layers under a sweater or jacket” while also looking great alone “with wide-leg jeans.” “This has to be one of my favorite long-sleeve shirts,” they raved.

The Layton Midi Slip Skirt

This now-$29 slip skirt paired with the above turtleneck and a pair of timeless knee-high boots might be the chicest combination you’ll wear this winter. Need I say more? Okay, well I’ll also add that shoppers say the midi-length skirt is a “stylish and comfortable option for dressing up,” a “beautiful, unique addition to [any] wardrobe,” and a compliment magnet.

During Madewell’s double-discount sale you can stock up on those winter staples your closet might still be missing while the brand’s entire sale section is an extra 40 percent off with the code NEWYEAR. Shop more of our must-haves from the sale-on-sale, below.

The Darcy Ankle Boot

V-Neck Relaxed Cardigan

Square-Neck Midi Dress

Denim Quilted Workwear Jacket

Superwide-Leg Jeans