Madewell's Winter Sale Is Live With an Extra 30% Off Fan-Favorite Sale Denim, Sneakers, and More

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There’s no better way to start the new year than with a fresh outfit. And whether your sizes have fluctuated because of holiday feasting or you’re missing reliable pieces, Madewell is helping guys kick off 2024 in style with its winter sale.

From now until January 8th, you can save an extra 30% off sale styles like bestselling men’s denim, sneakers, and basics, as well as some warm, wear-now jackets, sweaters, and accessories.

Because the men’s sale collection is so strong, styles are selling out quickly. So if there’s something you’re kind of into, make like Nike and “just do it,” because if you wait too long to buy it, we can all but guarantee that it'll be long gone when you check back.

If you’re curious about sizes, the best strategy here is to buy the two you’re torn between and send back the one that doesn’t fit. Some items are final sale, but that’s noted on the checkout page.

After Men’s Journal shopped through the Madewell winter sale, these are some of the products that stood out the most.

Madewell Men’s Athletic Slim Jeans, $80 (was $128) at Madewell

At Madewell, it’s all about the Athletic Slim-fit denim. Trends in men’s bottoms are leaning roomier, but it’s a welcome fluctuation for most because of the added breathing room in the seat and thigh. These jeans do exactly that and taper the leg toward the bottom to keep the tight-to-the-ankle look that many guys like from their slim-fit jeans. The brand has constructed these with some stretch, too, to help with flexing the knees. It’s a great pair of everyday denim that’ll get you through the winter and beyond. 

Madewell Men’s (Re)sourced Cuffed Beanie, $20 (was $35) at Madewell

Although Madewell does currently have Bill Murray’s bright orange Life Aquatic With Steve Zissou beanie for just $13, spend a few extra bucks for the yellow. It’s a very underrated neutral color and the perfect accent for the safe color palette in most of Madewell’s collections. Otherwise, it’s a great beanie in its own right that is made from both recycled cotton and polyester. 

Madewell Men’s Crewneck Pocket Sweatshirt, $56 (was $90) at Madewell

An off-white sweatshirt is one of the greatest layering pieces any man could have for winter; think of it as a replacement for the white T-shirt you’d wear in the warmer months. With a unique side-entry chest pocket, it acts as a blank canvas that allows you to contrast a darker flannel shirt, shirt jacket, or winter coat to be worn on top. And thanks to its cotton-poly blend, it’ll keep you plenty warm, whether catching a city train or sitting in a cold office.

Madewell Men’s Corduroy Perfect Long-Sleeve Shirt, $53 (was $90) at Madewell

Madewell’s Perfect shirts are supposed to do all the things guys wished a button-down shirt would do—look good untucked, not be too boxy, and remain comfortable throughout the day. That’s what this one in the “Warm Cinnamon” colorway does. Made from 100% cotton, this slim-fit shirt strikes each of the aforementioned chords to create a day-to-night smart-casual aesthetic that’s perfect for layering.

Madewell Men’s Fleece-Lined Bomber Jacket, $58 (was $148) at Madewell

There aren’t a ton of men’s jackets featured during the winter sale, but this fleece-lined bomber might be all you need. Perfect for cool temps hovering around the 50s and 60s, this bomber jacket will keep you cozy outside without making you sweat when walking around indoors. If you need extra muscle, it’s also got enough room to layer up with a hoodie or sweater. 

Madewell Men’s Court Sneakers in Colorblock Leather and Suede, $62 (was $98) at Madewell

One of Madewell’s best white sneakers, the Court is a nicer take on an old-school basketball shoe with modern construction and flare. Made as eco-friendly as possible, these minimalist sneakers feature leather from a Gold-certified tannery (presumedly from the Leather Working Group) and outsoles made from recycled rubber and rice husks. They also see the brand’s MWL Cloudlift tech, which is described as being “pillows for your feet.”

Madewell Men’s Kickoff Trainer Sneakers in Neutral Colorblock Leather, $70 (was $110) at Madewell

If the Kickoff Trainer is still available in your size in Neutral or the Moon Rock Multi colorway, scoop them up quickly. Retro running shoes have been a mega-hit in the men’s sneaker world as an alternative to the minimalist sneaker and a safe divergence from the overzealous Balenciaga styles that swallow legs. But we’ve worn these ones and are happy to say they’re super comfortable and make creating outfits easy. We like to rock them with our Madewell jeans and a comfortable shirt jacket. 

Madewell Men’s Garment-Dyed Athletic Slim Jeans, $74 (was $118) at Madewell

Another Athletic Slim style to grab is this garment-dyed pair of men’s jeans that comes in four discounted colorways—dark blue, green, gray, and off-white. This gray color is an excellent option for guys with more muscular builds who don’t want to draw extra attention to their bodies because of the matte color. They’re available in waist sizes ranging from 28 to 40 and in lengths from 30 to 34, meaning that’s a perfect fit for most guys.