What to Buy from the Madewell Men's Drop, According to the Guy Who Styled It

Something is very right in the Madewell men's department. Little brothers tend to be natural born chaos agents, which is why so many become actors, extreme athletes, or crypto traders. Yet Madewell, the younger sibling to J.Crew, is out here quietly killing it without a single cry for attention. After appointing ex-Gap honcho Luke Linder as head of men’s design (and calling up longtime industry guru Aaron Levine and former GQ deputy fashion director Jon Tietz to dial in the vibes), the brand’s fall collection kicked off a revamp that confidently channeled menswear’s reigning zeitgeist—statement knits, ’50s prep, ’90s Seinfeldcore—into a deeply cohesive, wearable whole. Now Madewell’s dropped the next chapter of the story: a new collection that has us thinking the little bro might end up the star of the family.

The Best of Madewell's Fall Drop

• The Swaddly Topcoat: Madewell Button-Front Topcoat In Italian Fabric, $398
• The Cozy Crewneck: Madewell Merino Wool-Blend Crewneck Sweater, $128
• The Geezer Cardigan: Madewell Merino Wool-Blend Cardigan Sweater, $138
• The Zippy Fleece: Madewell Half-Zip Mockneck Pullover Fleece, $98
• The Winter-Weight Hoodie: Madewell "McCarren" Hoodie, $98
• The Slouchy Suit: Madewell Roebling Blazer & Pleated Trouser, $475
• The Blanket-Soft Flannel: Madewell Brushed Easy Shirt-Jacket in Italian Fabric, $118
• The Juiced-Up Tee: Madewell Relaxed Tee, $40
• The Throwback Jeans: Madewell 1991 Loose Straight Jeans, $138

Imagine a room filled with all the clothes you’ll want to wear all the time for the next three months, and you’ll see them in Madewell’s new arrivals. A cyan cardigan that’s eye-catching without being shouty; a checked blazer that’s begging for some medium-wash denim and an oxford shirt; a slouchy sweater that’ll probably be better known as your Every-Damn-Saturday Sweater—it’s all there, and it’s all available at Madewell right this very moment.

To score you the lowdown on the best of the bunch—and some insight into how to wear it—we synced up with Madewell design consultant Aaron Levine, whose CV includes stints overhauling Club Monaco and Abercrombie, to help explain the magic behind Madewell’s new groove. Levine, GQ’s Cam Wolf noted in August, is famous in menswear circles for “dusting the cobwebs off of stale mass brands and finding the sweet spot between lazy sameness and high-fashion hijinks.” In other words, he’s exactly the type of guy you want in the driver’s seat when you’re shopping. Here are 9 things he’s especially stoked about from the latest Madewell men's drop.

The Swaddly Topcoat

"A beautiful, easy throw-on coat," Levine says. "The below-the-knee length is great, and immediately makes me feel more put-together." The Italian-milled fabric and slouchy-but-not-sloppy fit will do the same for you, too.

The Cozy Crewneck

Levine prizes this crewneck for its unbeatable cold-weather proposition: "soft and light, but cozy at the same time." Plus, he says, "the slightly beefier trim and relaxed fit are a vibe. I wear it with easy denim and hiking boots—you can go anywhere and feel good about it."

The Geezer Cardigan

Per Levine, this ultra-chill knit is the platonic "grandpa cardigan", thanks to the same ludicrously soft fabric featured in its crewneck counterpart. In sweaters, as in rugs, a little shagginess goes a long way.

The Zippy Fleece

The full-zip fleece co-opted by fast-talking Wall Street types isn't the only silhouette to put the fabric to good use. This is "an easy adaptation of a constant favorite," Levine says. Come for the goes-with-everything color and expectedly plush fabric, stay for that deep exaggerated zip.

The Winter-Weight Hoodie

Allow Levine and co. to introduce the hoodie you're going to live in well through winter. The ultra-beefy cotton fleece is new to Madewell's repertoire, but the cut—a '90s-inspired silhouette with what Levine describes as the "perfect length"—is vintage the whole way through. "My friend is always, like, 'Throw in a sweatshirt whenever you travel, you never know when it can come in handy,'" he says. "This is that sweatshirt."

The Slouchy Suit

The standout from Madewell's big menswear glow-up? Easy, elegant, impossibly right now tailoring exactly like this. For maximum comfiness, make like Levine and throw the whole set over a T-shirt or a relaxed knit—and don't be afraid to let the pants level up your usual bodega-run fare.

The Blanket-Soft Flannel

Levine might be a little biased when he calls this the "perfect fall flannel", but he's hardly exaggerating. The fabric is thicker than a bowl of stew, the pattern is endlessly versatile and ideal for layering, and the sizable collar will, in Levine's words, make you "feel fancy" when you'd rather be swaddled in a sweatshirt.

The Juiced-Up Tee

You've heard of bulking season, right? Now apply the same logic to your tees. This one's cut beefy and relaxed, ready-made to "layer under all of the above," Levine says—and hold its own when you need to shed the sweaters.

The Throwback Jeans

When Levine refers to this silhouette as "just a great relaxed, easy straight jean," he's being characteristically humble. Madewell's bread and butter has always been denim; jeans like this—roomy through the thigh with a straight leg—uphold that legacy for fellas who finally feel ready to ditch the slim cuts for good.