All products and services featured are independently chosen by editors. However, StyleCaster may receive a commission on orders placed through its retail links, and the retailer may receive certain auditable data for accounting purposes.
There are a handful of high-quality, affordable brands that specialize in closet staples you can wear season after season and year after year. Without question, you can count Madewell as one of them—I mean, it’s literally in the name. If you’re searching for clothing that’s built to last and designs that transcend fleeting trends, you’ve come to the right place, especially because Madewell’s Black Friday sale is live as we speak.
From November 9 through November 19, take 30 percent off of your purchase (exclusions apply) with promo code LETSGO. With a discount like this, you can revamp your entire winter wardrobe for less—at least, that’s what I plan to do.
I’ve been a fan of the brand’s denim for quite a while now, and one of my first pairs of Madewell jeans made me realize the importance of quality and feel. I remember wearing my wide-leg jeans literally nonstop because they were so comfortable. I could do anything in those pants—lift heavy boxes, walk up a flight of stairs without developing a wedgie, wander around all day, you name it.
Even better: Those jeans are still hanging in my closet as I sit here and write this story. We’re going four years strong, and to me, they’re still in mint condition. Through all of the wear they’ve gotten, you could never tell they’ve been through so much in the past several years. And the fact that Madewell makes timeless silhouettes is evident. My personal style has changed a lot since 2019, but you can still catch me reaching for my cropped wide-leg jeans now and then.
I’d like to point out that Madewell carries much more than durable denim. I always check out its sweaters and outerwear. The brand has any kind of chunky knit or button-down cardigan you might need. But the coats? Seriously stunning options if you ask me. Madewell’s jackets and coats are a bit more of an investment, but the quality and timelessness make the purchase well worth it.
At this point, you’re probably tired of hearing me gush over the brand and are itching to add items to your cart, but let me help save you some time. Ahead, find my top picks from Madewell’s Black Friday sale.
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Wide-Leg Jeans
Image Credit: Madewell. All products and services featured are independently chosen by editors. However, StyleCaster may receive a commission on orders placed through its retail links, and the retailer may receive certain auditable data for accounting purposes.
It’s only fitting that my selects start with Madewell denim, since that’s exactly what initially got me interested in the brand. I’ve been gravitating towards baggy jeans lately, but think I want to branch out into super long, wide-leg styles like this pair.
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Turtleneck Sweater
Image Credit: Madewell. All products and services featured are independently chosen by editors. However, StyleCaster may receive a commission on orders placed through its retail links, and the retailer may receive certain auditable data for accounting purposes.
This turtleneck sweater is so versatile that you could wear it to a holiday party, work, date night, or perhaps even a cozy ski village (to me, it’s giving Aspen).
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Off-The-Shoulder Top
Image Credit: Madewell. All products and services featured are independently chosen by editors. However, StyleCaster may receive a commission on orders placed through its retail links, and the retailer may receive certain auditable data for accounting purposes.
I never know how to dress for grabbing drinks or going out when it’s 30 degrees. I want to look cute, but also don’t want to look like a puffy marshmallow. This basic off-the-shoulder top (made from a chunky knit fabric) seems like the perfect compromise: It’s both stylish and warm.
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Sling Bag
Image Credit: Madewell. All products and services featured are independently chosen by editors. However, StyleCaster may receive a commission on orders placed through its retail links, and the retailer may receive certain auditable data for accounting purposes.
The Sling Crossbody Bag immediately reminded me of The Row’s $2,350 cousin. A chic, leather sling bag seems like the perfect winter accessory to keep all of your essentials safe (and dry). This crossbody is made from smooth leather, features an adjustable strap (you can wear it multiple ways), and has a handy exterior slip pocket for your phone.
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Cargo Pants
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In case you’re deciding whether you need another pair of cargo pants in your closet, the answer is yes. The Harlow is made from Madewell’s lightweight brushed (Re)generative chino in transitional regenerative cotton and comes in a stunning olive green shade that matches almost anything.
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Sweater Vest
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For those who don’t get true winter temperatures where they live, or maybe you just run warm, a sweater vest is the way to go. It’s not so heavy and chunky that you’ll sweat right through it, but it’s thick enough to keep you from freezing. This tiny sweater vest would look fab with high-waisted jeans or trousers.
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Oversized Sweater
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I’m a huge proponent of oversized sweaters like this one. This is the kind of garment I’d want to live in all winter long because it’s cozy, crewneck, and loose-fitting so there’s room to layer underneath.
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Coat
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The Gianna Coat is unique in that it’s woven in Italy from a blend that includes traceable and sustainable NATIVA™ certified wool (and a hint of cashmere). This innovative material is toasty and naturally water and wind-resistant, per the brand. Whether you’re pairing it with sweats and a hoodie or a holiday dress, this double-breasted topcoat makes any outfit more sophisticated.
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Relaxed Sweatshirt
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I normally stick to neutrals (could you tell?), but I’ve been seeing vivid greens, reds, and blues everywhere and think it might be time to spice things up. Instead of layering a light grey hoodie under a long black coat, I’d experiment with a pop of color like this terry sweatshirt.
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Boots
Image Credit: Madewell. All products and services featured are independently chosen by editors. However, StyleCaster may receive a commission on orders placed through its retail links, and the retailer may receive certain auditable data for accounting purposes.
A trusty pair of black boots is a winter must-have. Since wearing boots with tall heels might not be the most practical move during the colder months, opt for a kitten-heel boot. This style is made from Madewell’s MWL Cloudlift Lite padding, which makes walking in heels easier than you’d expect.
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