Number three is a game-changer.

By Allison Chesky
Updated July 20, 2015
Pile of folded jeans, silo
Credit: hilmi_m/Getty Images

When you invest in denim, it’s the beginning of a long (and intimate) relationship—and just like with any other long, intimate relationship, you want the pair you invest in to be the "one." Faced with the hundreds of options available online and in stored, this can feel like a nearly impossible decision to make. How do you pick the right brand, the right size, the right silhouette, the right wash? These six simple rules will help make sure the pair you choose will serve your body and your lifestyle just right.

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Pile of folded jeans, silo
Credit: hilmi_m/Getty Images

1 Define your size.

Since many contemporary brands size their denim according to waist measurements, it’s best to measure yourself for the most accurate fit. Using a flexible measuring tape, take a measurement from your natural waist (the smallest part of your waist), and round down to the whole number. So, if your waist is 28.5 inches, you would be a size 28. Once you know your size, variations are slight across brands. That means the rest of the preferences on fit will boil down to other factors, like the leg silhouette and the rise. Remember: The hardest thing to alter on a pair of jeans is the waist, so never compromise on the fit of the waistband.

2 Understand the fit.

When choosing between sizes, skew on the fitted, tight side, since the stretch fibers in most skinny jeans will bag out with wear. If you don't like how high or low the jeans hit your waist, look for clues pertaining to the rise. A pair that’s marked “mid-rise,” which is typically at least eight inches, provides more coverage because it hits higher on the waist, so it will contour to reveal less overall. Don’t try to size up if the rise is too low; that will only lead to a poor, uncomfortable fit. Instead, look for a different style that fits your body and comfort level.

3 Length is negotiable.

Making adjustments to the inseam is a minor alteration, but jeans should be altered with the shoes they’ll ultimately be worn with. Flares, which are best suited to heels or wedges, should fall about an inch from the floor, while skinny jeans should hit just at or above the anklebone. To give an of-the-moment look to dark inky skinny jeans, you can even cut the hem to reveal a raw edge.

4 Let the silhouette and wash work for you.

Want to downplay hips or create the illusion of longer legs? Choose dark, whisker-free flares or trouser jeans that almost touch the floor. If your legs are your best asset, play them up with lighter washes or added details like distressing or moto seaming. Rather not show off your calves? Look for a monochromatic wash and a cigarette leg that will fall straight down from the widest part of your calf. Cast a wide net, and bring a varied haul—of styles, washes, and even sizes when it comes to new brands—with you to the dressing room however daunting it may seem. You never know, a pair that doesn’t have hanger appeal could be supremely flattering on the body.

5 Take a 360-degree approach.

Before committing, do a test run. Stand in front of a three-quarter mirror to see how the jeans look from the behind. Then sit on the dressing room bench and do a squat or two to ensure there’s no discomfort, that the denim doesn’t stretch out, and that you won’t be revealing too much.

6 Stick with what works.

Peggi Jewell, Vice President of Merchandising & Design for 7 For All Mankind says her foolproof advice is: “Keep it simple. Know what fit works best for your body and makes you feel confident and then stick to that fit. It’s like knowing what haircut works best with your face shape.” When you've landed on a brand or style that works for you, let that be your jumping off point, and mix it up with washes and minor variations in silhouette. Last of all, be patient. In the end, it’s a worthwhile process.