best of brand

The Strategist Guide to Shopping at Madewell

Photo: Courtesy of the vendor

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 (which appears further down on this list). The rigid-looking denim is actually anything but, she assures, making these “perfect” for lounging and everyday wear — without looking zhlubby.

“Until I put on the Emmett pants, I assumed I’d just have to sit out the wide-leg crop trend, since all of the pairs I tried before looked ridiculous on my short legs,” writes Strategist senior writer Karen Iorio Adelson, who clocks in at just under five feet. The petite-fitting Emmetts (which also come in regular and tall fits), she says, hit her legs at just above the ankle, and their “slim” wide leg “doesn’t overwhelm my frame.”

While these came recommended by Madewell CEO Libby Wadle (who may, understandably, be biased), we can’t disagree with the issue she says the jeans were designed to solve. A problem with vintage high-rise denim, according to her (and most people who have tried on a pair), is that the lack of stretch can often be uncomfortable. Enter this “Comfort Stretch edition” of Madewell’s Perfect Vintage Jeans, which Wadle promises has the “perfect amount of elastic, so if you want that retro look, you can actually look cool and comfortable.”

After a doula recommended these Madewell Maternity Skinny Jeans to her, Strategist writer Lauren Ro says they became a go-to while she was pregnant. The jeans have a comfortable pull-on design, a faux-zipper panel, and a stretchy, over-the-belly band that “tapers in the back so that you’re not completely enveloped in extra fabric,” according to Ro.

Madewell’s Momjean is a favorite of celebrity stylist Samantha Brown for its tailored leg, which “helps to keep the silhouette flattering and not dumpy.” They also have the “perfect amount of stretch,” she adds, so they won’t constrict or lose their shape.

“When it comes to skinny jeans, the higher the rise, the better,” according to plus-size brand consultant Sarah Chiwaya, the founder of Curvily. She loves Madewell’s “Curvy” version of its High-Rise Skinny Jeans, which go up to a size 37 and are made to accommodate an hourglass shape: They have an 11-inch rise, a contoured waistband, and extra room in the hips. “The medium wash is super-versatile, and the painted-on fit makes my legs look wonderfully long,” Chiwaya adds. Stock, right now, is limited, but you can still get them in a few different sizes.