Most Comfortable Jeans for Men

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The keystone of any man's wardrobe is a comfortable pair of jeans. Men will wear them for days at a time, and a good pair of jeans will last several years. Finding appropriate, loose-fitting jeans can be oftentimes troublesome, even for fashion-savvy shoppers. When shopping for the perfect, comfortable denim pants, go with the classic models. Regardless of brand, boot cuts and straight fits are the best fitting and some of the most comfortable jeans on the market.


"Esquire" magazine once called the Diesel's Kajo jeans "the only pair of jeans that should touch your legs." With a dark denim wash and rust staining finish effect, the Kajo jean ($75) is the perfect fit. Though rare, Diesel offers several other comfortable straight fits, including the Larkee ($170).

Levi's 501

The style that popularized jeans among youths in the 1950s, the Levi's 501 is the one of the most recognizable and iconic brands in American fashion. The 501s that Marlon Brando and Elvis Presley donned remain nearly unaltered today. Made from 100-percent cotton, the 2011 model has a straight body with a 17-inch leg opening. They come in two styles — original and shrink-to-fit — and 28 different colors. Prices for most 501 jeans range from approximately $44-$88.


Agave denims, such as 2011's Pragmatist selection, break from the cookie-cutter cotton weave and add a 2-percent elastane mix that provides a stretched material that allows room for legs to breathe. They are hand-woven in California and feature a zipper fly. Though Agave denims are on the pricey side at around $230, 2010's Agave Silver blues are a similar fashion and can be found in online stores, such as Sierra Trading Post, for approximately $60.

Banana Republic

For a refined look, Banana Republic is an outpost for durable and reliable jeans that lend a designer look quality without sacrificing comfort. Banana Republic offers four different, great-fitting styles — vintage straight, relaxed, boot cut and straight. The company's boot cut is a great option for those who are looking for versatile jeans that are perfect for work, outdoors or the casual night out. Prices for the Banana Republic boot cut blues are approximately $80.