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The Strategist Guide to Shopping at Madewell

Photo-Illustration: The Strategist; Photos: Retailers

Anyone who has shopped at a bigger-box store knows it can be hard to figure out where to begin. There are dozens upon dozens of options that all seem as worthy as the next, but the reality is that products from any given brand are not all created equal. When you shop as regularly as we do, you learn that many brands just do some things better than they do other things. Take Madewell, for instance — its seemingly limitless selection of basics like jeans, T-shirts, and tote bags can all start to look the same once you begin browsing. To help you narrow down which staples to add to your wardrobe, we combed through our archives to put together a list of all the most praised things from Madewell we’ve written about, from doula-approved maternity jeans to Strategist-editor-approved tees to affordable accessories that stand the test of time.


Madewell’s High-Rise Skinny Jeans — which are available in petite, regular, tall, and taller fits — are a denim staple. “I feel contained and smoothed in these jeans, and the waist comes up high enough [so] I don’t get that annoying gapping at the back,” says author and lingerie expert Cora Harrington of the Lingerie Addict. Plum Sykes, an author and Vogue veteran, also loves these for their “very, very high waist” and tailored fit. They look “just the slightest bit French,” she told us.

For a pair of jeans that looks a little more lived-in, travel and food writer Kat Odell recommends the distressed, slightly lower-rise version of the skinny jeans above (which also come in petite, regular, tall, and taller fits). “For years, I used to drop hundreds of dollars on designer jeans, including some Rag & Bone and J Brand, but these are absolutely my No. 1’s now,” she says. “I basically live in them.”

“I have 20-something pairs of jeans, and I probably wear these Madewell ones the most,” says Strategist writer Chloe Anello of this more relaxed version of Madewell’s Momjean. The rigid-looking denim is actually anything but, she assures, making these “perfect” for lounging and everyday wear — without looking zhlubby. Stock is limited right now, but you can still get them in a few colors and sizes.

Celebrity stylist Samantha Brown loves Madewell’s signature vintage jean. It’s cut slim through the leg, which “helps to keep the silhouette flattering and not dumpy,” she says. “It also has the perfect amount of stretch so it’s not constricting and doesn’t lose its shape with wear.” Brandt told us she recommends these jeans to her roster of clients — including virtual ones — since they fit “just about anyone” and come in a wide range of sizes.