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.

“I get lots of compliments on them. And I’m not normally someone who gets compliments on jeans,” says actress and Bitch Sesh podcast co-host Casey Wilson of these Madewell jeans. She adds that the light stretch and relaxed fit also made them comfortable enough to wear while pregnant. They come in petite, regular, and tall fits; stock, again, is limited, but there are still a handful of sizes to choose from in all of those fits.

Strategist senior editor Casey Lewis has been a fan of these High-Rise Knit Leggings since 2008, lauding them for their substantial stretch, accommodating waistband, and opaque fabric. “I currently have five in my drawer, one on my body, and two on the way,” she recently wrote. “I’ve found myself wearing them morning to night.” Clearly, other shoppers agree, because the leggings — while still available — are also in limited stock right now (sizes include XXS, XXL, 2X, and 3X).


When we asked cool women about their go-to T-shirts, design student Sabrinna Fabi told us that Madewell’s Baby Tee is “my all-time favorite.” She was surprised by how stretchy it is — “it hugs your body really well” — given the shirt is made from fabric that she says is “much thicker than your average tee’s.” Another detail to like: its “cap sleeves with the crinkled edges.”

Both Strategist editors and Brooklyn-based fabricator Chelsea Scott swear by the Madewell Whisper Cotton V-Neck Pocket Tee, which comes in a multitude of colors. According to us, it’s soft and has a flattering drape. And according to Scott, it “works perfectly with a simple, toned-down outfit.”

While we are moving out of layering season, Strategist writer and avid turtleneck-wearer Hilary Reid says this thong-style turtleneck bodysuit is her favorite for just that. Its design, she says, ensures that your “tucked-in turt” stays put. (Given its sale price and seasonality, this is also in limited stock right now.)


The Transport Tote made our list of women’s wardrobe essentials because cool ladies we know swear it is one of the best bags (for work and life) you can buy. “I do not have very exciting or expensive tastes in handbags,” says Deb Perelman of Smitten Kitchen, who told us she’s on her second or third Transport Tote. She likes that the handle length allows her to fit the bag over her shoulder even when she’s wearing a “puffy jacket,” and that the main compartment is roomy and sturdy enough “to hold a laptop, water bottle, and all the toys my kids swear they want to play with.” Madewell’s complimentary personalization service, we should add, also makes this bag a great gift (and if you don’t want to take our word for it, just ask the college graduates who recommended it as one).