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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.

Bottoms

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.

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 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.

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.” While the style comes in four washes (“Pure White,” “Lanette,” and “Starkey”), Sokolov prefers the “Black Sea” wash, shown, for its raw hem and ripped knees.

“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.

Former 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.” While all sizes are currently in stock, they’re selling fast given the sale price and approaching holiday. So as we like to say, don’t dillydally.

Tops

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.”

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).

Former Strategist writer 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.

Shoes

Photo: Retailer

These loafers are a favorite of photographer and blogger Denisse Myrick, a self-described “big fan of Madewell” who owns over ten of the brand’s bags and “tons” of its shoes. She likes these for their “stunning” mahogany color and slim profile that look equally great with a dress or trousers and a tee. (They also come in black.)

Alternatively, these more contemporary lug-sole loafers have the “perfect amount of chunkiness,” according to Anello, who says they fall into the sweet spot between sophisticated and versatile. Compared with the above Frances loafer, these are “much more of a modern-day loafer,” Anello adds, “without being so trendy that they’ll go out of style in a month.”

Accessories

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). Just note that personalized items won’t arrive in time for Christmas this year.

The slightly more petite Medium Transport Tote is “quite literally the perfect medium,” according to graphic designer Meagan Sapashe, who says it’s big enough to keep all of her day-to-day essentials at hand without being too bulky. Unlike the regular Transport Tote, it has two different sets of straps: Two short top handles, plus a detachable shoulder strap that allows you to wear it across your body. And it’s not just a favorite for working professionals — teens have told us “it’s the perfect size bag to bring anywhere and be able to fit anything into.”

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.”

These see-through pouches are Strategist writer Dominique Pariso’s favorite for storing toiletries and cosmetics. “They’re affordable, the half-moon shape looks snazzy, and the clear vinyl lets me see all my products, so I’m not digging around for my lip balm,” she writes. The larger one is better for bigger toiletries, according to Pariso, while this smaller one is best for makeup.

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