The Best Jeans For Older Men That Are Stylish And Comfortable

Waist sizes: 30 to 44 inches | Length: 30 to 34 inches | Colors: 3 total

For a casual cool look with a pulled together silhouette, try this subtly distressed pair. They feature classic five-pocket styling with a hint of stretch for comfort. These have a tailored fit, so it’s recommended that you size up when size when purchasing.

Waist sizes: 28 to 46 inches | Length: 28 to 36 inches | Colors: 7 total

The perfect jeans have structure and stretch, and this pair moves with you but also has good fabric snapback so the fit remains crisp throughout the day. These also come in five different fits­—tailored, slim taper, slim, athletic and straight—and five lengths, so these jeans are just about as bespoke as you can get.

Waist sizes: 28 to 38 inches | Length: 33.5 inches | Colors: 5 total

If you like your jeans paired with a white tee or button down, then go for this casual-yet-refined pair. It has a mid-rise fit, button fly and fits straight through the hip with a slight taper from the knee down. There’s also a tiny bit of stretch in this pair, so they won’t feel overly rigid or restrictive.

Waist sizes: 27 to 44 inches | Length: 29 to 36 inches | Colors: 20

Levi’s 501 jeans are iconic for a reason—they tend to fit most body types well, they feature classic style details and they’re durable and hardwearing. This straight leg style has been the epitome of American masculinity since 1873, and while the original versions featured no stretch, some pairs now have a tiny bit of stretch in the fabric for comfort.  

Waist sizes: XS to 3XL inches | Length: 28 to 35 inches  (inseam alteration is available) | Colors: 6 total

While many guys may not want to try jeans with a streamlined silhouette because they can be restrictive, this pair has extra stretch so you can move comfortably. They feature an internal pile lining that feels cozy and soft, and the stretch waist has a hidden internal drawstring so these jeans are ideal for everything from long days at the office to flights and travel.

Waist sizes: 28 to 42 inches | Length: 30 to 34 inches | Colors: 7 total

Some denim styles can skew oversized, sloppy and dated—what you’d think of as classic “dad jeans”—but Faherty’s modern take is both relaxed and pulled together at the same time. This slim straight pair is fitted through the hip and thigh, and the straight leg tapers ever so slightly at the opening. These have a bit of stretch, too, so you’ll reach for them often.

Waist sizes: 28 to 38 inches | Length: 30 to 36 inches | Colors: 4 total

J.Crew jeans are beloved for their quality and wide variety of fits. While this specific pant comes in traditional blue denim colorways, we like adding a bit of variety to your wardrobe with this garment-dyed pair. A chino denim hybrid, these look great paired with everything from tees to button downs to blazers. These also come in a slim fit.

Waist sizes: 28 to 38 inches | Length: 30 to 34 inches | Colors: 4 total

The elevated menswear from Todd Snyder is coveted for a reason, and their denim selection is as expansive as it is stylish. This classic mid-rise pair is straight through the leg, so it’s neither skinny and tapered nor voluminous. We love the medium crease wash for its elevated crease and perfectly faded and whiskered finish.

Waist sizes: 29 to 42 inches | Length: 30 to 34 inches | Colors: 23

Sometimes you need a dress jean, and this pair in a refined dark color has a polished feel, especially when paired with a sport coat or cashmere sweater. The mid-weight fabric has added stretch, and the waistband is contoured—meaning, it’s slightly higher in the back—so you’re always comfortable. 

Waist sizes: 28 to 44 inches | Length: 30 to 34 | Colors: 5 total

This style is neither too-baggy nor too-skinny, making it a versatile style staple. Wear these jeans cuffed to show off some ankle with a classic loafer or oxford. This pair comes in three classic blue washes as well as black and white. 

Waist sizes: 28 to 44 | Length: 32 to 34 | Colors: 3 total

Few fashion mistakes can age you more than a too-baggy pair of jeans, but this style elegantly follows your leg line without adding volume or being restrictive. It features five-pocket styling and has a bit of stretch, but it doesn’t have an overly thin fabric as can be the case with some stretchy styles.