The Strategist Guide to Shopping at Levi’s

The Levi’s Wedgie Straight Jeans made our list of the very best mom jeans for how nice they look on all body types. Sara Zucker, director of social media at KORRES, says they have “a leg that’s slightly slimmer than your standard mom jean.” “They’re popular because they fit you like you want old 501s to fit,” explains Bird clothing founder Jennifer Mankins: A “perfect straight leg, but with a bit more of a generous, modern cut.” She describes the rise as “high, but not too high,” and the jeans have a subtle stretch that Madewell designer Joyce Lee says makes them “super comfortable … without losing an authentic vintage look.” Dianna Cohen, the founder of hair-care line Crown Affair, calls the Wedgie Straight Jeans a daily staple, even for working from home. “It’s the only pair I’ve worn frequently at home during [the pandemic] — they’re almost as comfy as sweatpants,” she promises. “They look as great on when they’re still tight and just out of the wash as they do once they’re more worn and loosen up through the week.” Celebrity stylist Ali Levine describes their relaxed fit as modern while “still hitting the right notes for a mom jean,” and Richer Poorer brand director Allie Greenberg adds that, with 26- and 28-inch inseam options, they’re “great for shorties like me.”

“It took me 34 years, but I finally tracked down the perfect jean,” designer Susan Alexandra says of these oversize, relaxed-fit jeans that she notes “are often sold out” (a telling sign of their popularity). They’re a “wardrobe staple,” she adds, as well as a convincing dupe for vintage denim. “I had mine nipped in the waist to give them that perfect ‘I got these at a flea market in Berlin’ look.” College student Sylvie Nelson also swears by these jeans, calling them an essential part of her “comfortable stay-at-home uniform that still makes me feel cute.”

Former Strategist senior editor Casey Lewis owns the shorts version of Levi’s 501 Women’s Jeans, naming them a great alternative to a full-length pair when working from home. “Although I was tempted by the Ribcage and Wedgie fits, I ultimately went with the classic (and less constricting) 501s,” says Lewis, who got hers in a size up so that they’d be “extra comfy.” (She also bought the longer knee-length version so she could further cut them herself.) Strategist contributor Maria Dueñas-Jacobs, the founder of kids’ jewellery brand Super Smalls, has also recommended 501 shorts (though she prefers buying them vintage rather than new): “Like jeans, I can never get enough.”

While writing our guide to the best teen-girl gifts, we learned that lots of teens are skipping jeans in favour of overalls. These new but purposefully faded ones have a cool vintage look — and a very reasonable price tag.

A solid denim jacket is just as much of a wardrobe staple as a good pair of jeans. New York–based creative consultant Michele Janezic owns several vintage and new Levi’s jean jackets. “One is a well-loved boxy classic, another is a fitted ’70s orange tab, and another is an oversize boyfriend fit,” she says. She keeps this oversize trucker jacket in medium wash on permanent rotation when the weather is cool.

Or for chillier days where you want something with a bit more warmth, this sherpa-lined denim jacket comes recommended by trend forecaster Melissa Moylan. She notes that it taps into the ’90s-throwback looks that are currently popular, especially with teens. “We’re seeing oversize jean jackets trend in a big way,” Moylan says. “Levi’s ex-boyfriend style works in a relaxed silhouette with the addition of sherpa lining for winter.”

As noted above, many of the guys we’ve talked to about jeans really love Levi’s 501s. Garnering praise from denim experts, writers, podcasters, and former Strategist columnist Chris Black, they are without a doubt the most recommended pair of men’s jeans we’ve written about to date. “If we’re going to talk about jeans that every man should have in their closet, a pair of good-old Levi’s” is a must, according to denim expert and writer Amy Leverton, who calls 501s the gold standard of men’s denim. Former Strategist writer David Notis is also a fan, calling out the jeans’ “strong hardware and 100 percent cotton” material, which he says is non-stretch and therefore tends to hold its shape better as the jeans age. Jeremy Kirkland, the host of men’s style podcast Blamo!, swears by 501s, too, because their high rise makes them easier to dress up. “I’ve always been a fan of higher-rise jeans versus the lower-rise pairs because I wear tailoring and sport coats, so it helps to wear something totally high,” he says. Summing it all up, 501 fan Black says the jeans are “perfect for every occasion.”

For our Insider Goods series, we spoke to several cowboys about what to buy to achieve an authentic “yeehaw” style. Nick Villanueva, the public relations chair of the Colorado Gay Rodeo Association, notes that tight-fitting jeans have always been a staple. “From what I read in interviews all the way back to the 1980s, with regard to jeans, you have to have a quality-fit pair of Levi’s,” he says, adding that they’re still what’s worn the most.

“Skinny but not skintight” is how Netflix brand and editorial manager Alex Simons describes the fit of these jeans. He promises that they’re “comfortable from the moment you put them on” and that they have the “perfect amount of pocket space.” Simmons adds that he was a “fancy-jeans guy for years,” opting for pricier pairs from brands like Marc by Marc Jacobs until he tried these on and, as he puts it, “never looked back.”

The Levi’s 511 is to slim-fit jeans as the 501 is to straight-leg jeans: a standard-bearer. Menswear writer Tim Melideo told us that 511s are a staple in his wardrobe, and stylist Brandon Garr likes them, too — especially their price, which he says allows him to “be a little bit more daring in them because I don’t have to worry as much about the replacement cost if they get a little roughed up.” And Chef Jacques Torres appreciates that these “give a little bit, so if I gain a couple of pounds, I don’t have to change my jeans.” He compares bad jeans to bad knives: “If you feel like your jeans are a prison and you don’t feel good in them, then you should change your jeans. There is no reason to wear bad jeans, just like there is no reason to put up with a bad knife,” he advises.

When we asked cyclists to recommend the best men’s jackets to wear while biking to work, Robert Evans, CEO of Cycling Quests, suggested a classic Levi’s denim trucker jacket. “If it’s not wet and I’m feeling kind of hippy-ish, I’ll wear spandex shorts and a jean jacket on top,” he says. Evans owns several Levi’s jean jackets and likes their “iconic styling,” declaring that “the rest just don’t look as cool.”

We knew this Levi’s crewneck sweatshirt was a hit when it was recommended to us by four different guys in the same week. Andrew Favorito, who works in public relations for skin-care brand Tatcha, calls it “the coziest, chicest sweatshirt I’ve ever owned,” explaining that “because it’s modeled after a 1930s original, the fit is somewhat different: Slightly shorter in the torso, a little baggier, and a looser neck, which together with the vintage detailing and stitching makes it perfect.” We heard similar praise from Joshua Katz and Ben Starmer, the co-founders of CBD brand Dad Grass. Katz owns a whopping seven versions of this sweatshirt, and Starmer told us he owns two — both of which he’s washed “probably 100 times” without any significant change to their look or feel. And Drew Westphal, who works in digital marketing, calls it his “go-to crewneck” and appreciates its simple, “utilitarian” design.