How To Know If Your Jeans Will Really Be Comfortable

It feels like the most important wardrobe staples are the most difficult to shop for — my life is like a never-ending search for the perfect white tee or black blazer. And when it comes to jeans, my favorite, most comfortable pairs are usually found by accident. The best pieces pop up when you're not looking for them, right?

Denim is its own special beast when it comes to shopping with comfort in mind. Usually, it takes a few months (or years!) of blood, sweat, and tears to make a pair really break in and feel like a second skin. Hey, it's okay to have high expectations for your denim. As what's likely the most-worn item in your closet, jeans should fit the requirements you set. You want your go-to pair to be structured, but not too stiff, stretchy but not shapeless, and flattering but not restrictive.

It's hard to know denim's true personality from just five minutes in the fitting room. Half the time, once you wear a new pair of jeans out for a whole day, they become a totally different pair from the one you tried on. The knees stretch out, the buttons and tags bother you all day long, and they lose their shape after just a few washes. Talk about a nightmare.

To save you the headache of searching for a pair of jeans that's actually comfortable once you get them out of the store, we talked to four experts to make the search for great denim a bit more enjoyable. Enter: Will Redgate of BlankNYC, Paige Adams-Geller of Paige, Jessica Dunn of Big Star, and Jac Cameron of AYR, here to save the day.

From stretch to rise and everything in between, we broke down the most important elements when it comes to ultimate denim comfort. Read on for their expert tips and tricks. You'll never suffer through a sub-par pair of jeans again.