My Hunt for Relaxed-Fit Men’s Pants That Don’t Make Me Look Like a Toddler

I’ve long been a fan of Rhythm’sclassic fatigue pants, so I was intrigued by this pair of relaxed-fit jeans, which have a looser, flowy fit in the thigh and throughout the leg. I have to hike them up slightly or cuff them, or else they drape past my heel, but sometimes I like that baggier fit, which is reminiscent of ’90s skater jeans, although not nearly as baggy. (See skate legendChad Muskain a 1995 Maple Skateboards ad.)

At first glance, I wouldn’t consider these Alex Mill pants “relaxed fit.” They have a tapered leg and a seamed cuff. But they’re very roomy around the thigh — almost as relaxed and flowy as the Rhythm jeans above — which is why they’re on this list. I bought these pants almost three years ago, and they haven’t shown any signs of wear. I also have thechino versionof these pants in an olive-green color.

This pair of relaxed-fit jeans from Adsum are my most-worn pair over the past two years. On me, they have a straighter fit compared tohow they look on the model(the opposite of the J.Crew Giant Chino dissonance), but I think they’re still roomy, especially around the thigh. I think a pair of pants becomes too skinny when you can see the outline of your calf, and when the crease around the back of the knee becomes more pronounced. These Adsum jeans stay on the relaxed side by still providing that structure around the knee and through the lower leg.

These are the same cut as the darker wash above, but lighter. The pair I bought at a sample sale was a bit long, so I cropped the bottom hem with scissors.

This corduroy pair from Rhythm has a generous fit in the thigh and a slight taper toward the ankle — and I think that’s the winning combo I was looking for. They hit right below the ankle, so when I wear sneakers, the hems crease slightly without spilling over, like a pair of truly relaxed pants.

This pair from Toast is the widest-fitting pair I own. I’d say they’re as wide as the J.Crew Giant Fit chinos, but the pleats give them a narrower silhouette. Toast doesn’t list a specific inseam measurement on its site, but I measured it at 28 inches. Because of their rise, I have to pull them up a little higher on my waist if I don’t want to cuff them (for reference, the model in Toast’sphotois six-foot-two and still cuffs his medium pair). But my favorite feature is the weight: They’re made from a thick cotton canvas, so they provide a nice shape without being too billowy.

These Madewell jeans are just a touch more relaxed than my other straight-fit pants, and I think they’re right on the money with the fit I was looking for. (Madewell calls this the “loose straight” fit, which I think is a very accurate description.) They have a weight to them that lends structure: They often crease a little around the knee, and that breaks up the silhouette a bit. (Compare that to the cut of a baggier pair of jeans, like the Rhythm Essential Jeans above.) They have a shape-shifting quality, too: In some pictures, they look wide — but not too wide — and in others, they look like a straight-fit pair. It’s exactly the illusion I wanted in my jeans. Plus, this dark-gray wash is really versatile — I can wear them with sneakers, brown and black leather shoes, or a pair of loafers. And no matter what I wear them with, the jeans look current without calling any attention to themselves.

Although this is technically the same fit as the Madewell pair above, this specific wash is made with 21 percent Lyocell and is looser and billows a little more than the Hanlon, which is made from 100 percent cotton. It has a texture that drapes a bit more loosely over my legs. (If they weren’t labeled, I would have thought they were a completely different fit.) They don’t have as much structure as the Hanlon Wash — my legs swim a little in these — but they aren’t as wide as the Toast pants. I like how I can wear these jeans for dressier outfits.