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My hunt for relaxed fit pants (but not too relaxed)
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My hunt for relaxed fit pants (but not too relaxed)

Photo-Illustration: The strategist; Photos: Jérémy Rellosa

THE big pants the trend never really worked for me. As baggy pants have become more and more fashionable in recent years, I was hoping to join the club by adding a relaxed-fit pair to my rotation of slim, straight-leg pants. The looser silhouettes of pants I saw in ads looked tastefully flowy and voluminous on the models, but were often disappointing to me. I looked like a little kid trying on my dad’s clothes.

Although some people can pull them off, most big pants have a size-reducing effect on me (I’m five foot ten and normally wear a size 31 with a 30-inch inseam). I tried J.Crew’s Giant Fit chinos – perhaps the pair that brought big pants (back) into the menswear mainstream – a few years ago when the brand launched them. They have a loose, boxy fit – the kind of pants made for Stanley dish. Menswear writer Jake Woolf summed it up perfectly in his goodbye: “The cut is WIDE. Like, wider than you’d think seeing the gorgeous male model from the lookbook in it. When J.Crew says giant, that’s NOT bullshit. They were too wide for me. And if you swing too far in the opposite direction on the loose scale, you’re approaching skinny territory. I’ve found that most straight fits actually look like straight, slim pants.

My editor told me I might be looking for a pair of Carhartts. But I wasn’t looking for workwear-inspired pants – nothing with double knees or hammer loops.

So I’ve spent the last few years trying to find pants right in the middle of that scale — pairs that offer a looser leg and some structure, but aren’t too baggy. Below, the pants I found that came closest to that happy medium – and the pairs that hit the mark.

I have been a fan of Rhythm for a long time classic fatigue pantsso I was intrigued by this pair of relaxed fit jeans, which have a looser, flowier fit through the thigh and throughout the leg. I have to pull them up a little or roll them back, otherwise they stick out above my heel, but sometimes I like that looser fit, reminiscent of 90s skater jeans, although not as baggy. (See skateboard legend Chad Muska in a 1995 Maple Skateboards ad.)

At first glance, I wouldn’t consider these Alex Mill pants to be a “relaxed fit.” They have a tapered leg and a stitched cuff. But they’re very loose 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 show no signs of wear. I also have the chino version of these olive green pants.

This pair of relaxed fit jeans from Adsum are my most worn pair over the last couple of years. On me, they have a straighter cut than what they look like on the model (opposite of the dissonance of the J.Crew Giant Chino), but I think they are still roomy, especially around the thigh. I think pants become too skinny when you see the outline of your calf and when the crease at the back of the knee becomes more pronounced. These Adsum jeans keep it casual by still offering that structure around the knee and through the lower leg.

This is the same fit as the darker wash above, but lighter. The pair I bought at a sample sale were a little long, so I cut the bottom hem with scissors.

This corduroy pair from Rhythm is cut generously through the thigh and tapers slightly towards the ankle – and I think that’s the winning combo I was looking for. They hit just below the ankle, so when I wear sneakers the hems crease slightly without overflowing, like a really casual pair of pants.

This pair of Toast is the widest pair I own. I would say they are 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 size, I have to pull them up a little higher on my waist if I don’t want to roll them up (for reference, the Toast’s model photo is six feet two inches tall and still handcuffs his average 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 bulky.

These Madewell jeans are just a little more relaxed than my other straight fit pants, and I think they’re right up there with the fit I was looking for. They have a weight which gives them structure: they often wrinkle a little at the knee, which breaks up the silhouette a little. (Compare this to the fit of a looser-fitting jean, like the Rhythm Essential Jeans above.) Plus, this dark gray wash is really versatile — I can wear it with sneakers, brown leather shoes, and black or a pair of moccasins. .

While it’s technically the same fit as the Madewell pair above, this specific wash has a texture that falls a little more freely on my legs (if they hadn’t been tagged, I would have thought that (it was a completely different cut). They don’t have as much structure as the Munson Wash – my legs float a bit in them – but they’re not as baggy as the Toast pants. I love how I can wear these jeans for dressier outfits.

The strategist is designed to present helpful, expert recommendations on what to buy across the vast e-commerce landscape. Each product is independently selected by our team of editors, which you can view here. We update links when possible, but note that deals may expire and all prices are subject to change.