The Most Flattering Jeans (& vintage sizing tips)

When it comes to classic, flattering denim, “Vintage Levi’s 501s are pretty much the gold standard.” So says Elle magazine, which explains why you’ll see the little red tag in so many rear shots, and why they’ve been landing in closets for over 145 years!

But if that perfect vintage pair eludes you, there are other options out there—many with the same emphasis on non-stretch, 100% cotton, high-waist, rear-flatting cuts—and we did some sleuthing to find out what some of the best ones are…

First, if you do want to go the vintage route, Elle suggests being prepared to go up in size: “Vintage denim is much smaller than modern denim. When buying 501s, expect to go up at least two to three sizes from your regular waist. For a boyfriend fit, go closer to four sizes.”

Los Angeles stylist Jessica de Ruiter, in an interview for Jean Stories, said she likes to wear her vintage Levi 501s “One or two inches above the ankle bone. I like to see an ankle. It’s flattering on every body type, especially if you have curves, which most women do.” And on her preferred fit? “It’s not a boyfriend–it’s not baggy–it’s just straight enough so that it doesn’t hug your ankle or your knee.”

I asked the ladies at General Store in San Francisco, where there’s almost always a stack of vintage denim just begging to be tried, how to guess whether a pair might be a good fit when the sizing can be deceptive (and when trying on jeans can be, well, trying) and they taught me the craziest trick: if you hold the waistband around your neck and it touches in the back just so that the ends meet, the pair will probably be a good fit and it’s worth taking the time to try them on. And it works!

Where to find: Etsy, eBay, Re/Done, and you local thrift or resale stores

For an easier-to-find alternative to vintage, Levi’s is still the first stop: Their Levi Wedgie Fit is inspired by vintage Levi’s, and tends to have a 99-100% cotton content depending on the wash—though do double check. They also make a Levi Wedgie Straight Fit (no ankle taper), which I just got in the Grey wash.

Where to find: Levi’s sells the Wedgie in mulitple fits, including plus size. And Shopbop carries them, which means they’re 20-25% off right now during the sale (use code EVENT19).

Madewell’s Perfect Vintage Jean is very popular, and due to many customer requests, they have released a curvy version. Both run true to size.

Where to find: Madewell and Nordstrom

Citizen’s little sister, AGOLDE is a great source for sustainably made-in-LA denim, and the Riley cut is a really great straight-leg option. (I love the Vanished wash.)

They tend to fit true to size, though you can size up for a looser fit. Contributor Cary says she found a pair one size bigger than she needed at TJ Maxx, but they were a great price so she got them anyway and they are one of her favorites now!

Where to find: AGOLDE, Need Supply, and Shopbop (20-25% off with code right EVENT 19 right now).

Sézane’s 1967 Brut Sexy fit has a slim (though not skinny) leg, with the high-waist and structure of some of the other straight-leg options. They’re designed to fit every curve. We found the brand to run on the small side, and sized up.

Where to find: Sézane (in multiple color washes)

If you’re looking for something slimmer and with a little more stretch, the Carla High Rise from Able might be more for you.

Where to find: Able (note that if you sign up for their emails you can get 20% off)

The Everlane cheeky straight jean is a very affordable option that the brand says are “engineered for the perfect rear fit” thanks to pocket placement and a cut that lifts and tightens. According to reviews, these run large and stretch out after a few wears (they’re 98% cotton), so size down.

Where to find: Everlane

Do you have a favorite denim brand or fit to add? What are you wearing over and over? 

P.S. Favorite relaxed denim looks, and why I should probably never say never to trying new trends.

[Lead photo via Dôen and this post on sweaters / Photo of Jessica de Ruiter in vintage Levi’s by Katrina Dickson via Jean Stories / Agolde denim photos via Cheetah is the New Black and Charlie & Lee / Everlane Denim photo via Girl Meets Gold / Bottom photo via @hannahmas of General Store]

Related posts:

Travel Guides

Browse By Category