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The Strategist Guide to Shopping at Madewell

Photo-Illustration: The Strategist; Photos: Retailers

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Anyone who has shopped at a major online retailer 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.

Jeans and bottoms

From $80

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.” Stylist Sahra 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.

We crowned Madewell’s jeans the best overall for tall women after several stylish, five-foot-eight-and-taller women raved about the brand’s “tall” inseam length and especially comfortable cuts. Our jeans correspondent, Ambar Pardilla, reports “Almost all of Madewell’s jeans are offered in ‘Tall’ now, but ‘Taller’ fits are available on only select jeans and tend to sell out quickly.”

After interviewing plus-size writers, models, bloggers, and designers about their favorite pairs of jeans, Pardilla found that Madewell also makes the best plus-size jeans for women. Brown finds that the jeans are “supportive and hold her in, but aren’t suffocating when she’s sitting down.” Note, however, that Madewell jeans often run big, so you might need to size down.

From $40

Madewell’s High-Rise Skinny Jeans — which are available in petite, regular, and tall fits — are another 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.

Madewell Dadjean

“I have 20-something pairs of jeans, and I probably wear these Madewell ones the most,” says former 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.

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.

“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 a 10-inch rise, a contoured waistband, and extra room in the hips.

The petite and curvy version of the skinny jean above is a favorite of Social Goods co-founder Kate Sokolov. Being five feet tall with a curvy frame, Sokolov told us it was a struggle to find well-fitting high-rise jeans that weren’t “too high and too long.” But these “have a perfect rise for a short torso and an inseam that allows me to wear flats without having to get them hemmed.”

Madewell Harlow Wide-Leg Pants
From $50
From $50

When we spoke to Victorious star Victoria Justice about her favorite things, she told us about these linen blend wide-leg pants. They caught her eye when she walked past a Madewell store — and then she bought five pairs in five shades that same day. “I wear them all the time now with my Converse platform sneakers,” Justice says, adding that they’re more stylish than a regular pair of jeans. The pants are available in ten colors and come in petite, plus, standard, and tall fits.

Former Strategist senior editor Casey Lewis has been a fan of these Madewell leggings since 2008, amassing eight pairs in total, which she says she practically wears from morning to night. The material is substantial, stretchy, and not see-through, and the below-the-belly-button waistband doesn’t roll down. “It expands comfortably if you’re lounging on the couch or working from bed, but it also retains its shape,” Lewis says.


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.”

Lifestyle blogger Kristina Zias especially recommends this shirt for women with bigger busts because it’s loose but still has enough shape to show off your figure. She calls the denim fabric “extremely comfortable” and says the short sleeves are perfect for daily wear in warmer climates (like Los Angeles, where she lives).

Madewell Turtleneck Bodysuit

Strategist senior editor and avid turtleneck-wearer Hilary Reid says this thong-style turtleneck bodysuit is her favorite for cold-weather layering. Its design, she says, ensures that your “tucked-in turt” stays put.

Technically from Madewell’s men’s section, this vintage-inspired hoodie has become a favorite of Strategist junior writer Brenley Goertzen. Her boyfriend, who introduced Goertzen to the French-terry cotton sweatshirt, has it in four colors. For Goertzen, it’s the perfect oversize layer, and despite the draping fit, she says it never feels too heavy even on warmer days.

Accessories and shoes

Madewell’s Transport Tote is our best work bag; it’s been our favorite since Deb Perelman of Smitten Kitchen first recommended it to us in 2018. Perelman likes that the handle-drop length allows her to fit the bag over her shoulder even when she’s wearing a puffy jacket and that it’s spacious enough to hold a laptop, water bottle, and all the toys her kids “swear they want to play with.” Another fan, graphic designer Meagan Sapashe, says the tote is “quite literally the perfect medium” because it fits all of her daily essentials without being too bulky. Madewell’s complimentary personalization service, we should add, also makes it a great gift.

This slightly more petite Madewell bag has a top zip, and, unlike the regular Transport Tote, it has two different sets of straps: a set of short top handles plus a detachable shoulder strap that allows you to wear it across your body. It’s not just a favorite for working professionals — teens have told us that “it’s the perfect-size bag to bring anywhere and be able to fit anything into.”

When Strategist contributor Mya Gelber set out to find the perfect work tote, she wanted it to be a real workhorse with some visual charm. This task took her to the streets and subway of New York, where she stopped strangers to find out what their favorite totes were. A marketing director named Arianna Paranzino liked this tote because it fit her laptop and had a perfectly long strap.

As seen in our guide to the best loafers, these lug-sole numbers are our top pick for an affordable take on the style. They have the “perfect amount of chunkiness,” according to Anello. And because the Corinnes aren’t overly embellished, they’re “much more of a modern-day loafer,” Anello adds, “without being so trendy that they’ll go out of style in a month.”

Madewell’s well-priced ballet flat is a favorite of content creator Ella McFadin, who says they “feel like socks on your feet” because of how flat they are. They do offer more support than socks, thanks to some additional padding, so “they’re great for an everyday workday, for the commuter going into the office,” says McFadin.

If you’re looking for a sleek card case to replace a bulky wallet, restaurateur Emily Hyland says this one has served her well ever since she bought it to do just that. “It’s so easy to be minimalist and really carry what I need and just slip it in my pocket,” she told us. It’s durable, too: Hyland has had hers for years and says it has “[held] up really well.”

Strategist junior writer Bella Druckman purchased this zip wallet to match her leather backpack (also from Madewell but currently out of stock), but it comes in a neutral shade that goes with just about everything and has “enough space to hold all my cards and cash,” Druckman writes.

The Strategist is designed to surface the most useful, expert recommendations for things to buy across the vast e-commerce landscape. Some of our latest conquests include the best acne treatments, rolling luggage, pillows for side sleepers, natural anxiety remedies, and bath towels. We update links when possible, but note that deals can expire and all prices are subject to change.

The Strategist Guide to Shopping at Madewell