Countless menswear brands are pushing this old-timey style. Are these leg-lengthening throwbacks debonair—or unflattering and uncomfortable?

While younger generations might welcome belly-high pants, older men might not. ILLUSTRATION: Kagan McLeod

High-waisted pants—usually wide, often pleated—are trendy again. One millennial editor finds them super-suave, while a boomer editor feels oppressed when sporting them. They go to battle.

Jamie Waters: We know men’s pants have been getting wider. Less discussed, though, is the fact that lots of newer, roomy styles sit high on the torso—on or just below the belly button, instead of on the hips. I’m a huge fan.

Dale Hrabi: After trying them, I can judiciously say I hate them.

JW: I guess that makes us somewhat representative of our generations. While young-ish guys like me are embracing high-waisted styles, many over-50s seem to stick to regular, lower pants.

DH: That’s ironic, because high pants have mockingly been called “grandpa” pants. Do people who see them as part of a trend toward elegance know that?

JW: I reckon. Lots of these feel like a throwback, albeit a debonair one. Often they’re pleated, which adds to the old-timey vibe. Over the weekend we both tested a few pairs, including dress-pants, chinos and a buckled style called Gurkha pants. Did you find any remotely Cary Grant-like?

The high-waisted styles our editors tried, from left: Buck Mason Paperback Twill Full Saddle Chino, $158; Todd Snyder Italian Brushed Cotton Gurkha Trouser, $298; Suitsupply Wide Leg Straight Pants, $219

The high-waisted styles our editors tried, from left: Buck Mason Paperback Twill Full Saddle Chino, $158; Todd Snyder Italian Brushed Cotton Gurkha Trouser, $298; Suitsupply Wide Leg Straight Pants, $219

The high-waisted styles our editors tried, from left: Buck Mason Paperback Twill Full Saddle Chino, $158; Todd Snyder Italian Brushed Cotton Gurkha Trouser, $298; Suitsupply Wide Leg Straight Pants, $219

DH: Nope. High-waisted pants only work if you’re rail thin. If you have any sort of stomach, as many older guys do, they pinchingly cut you in half at your widest point—it’s uncomfortable and unflattering. You end up with a squashed torso at the end of very long legs. Not what I’d call elegant.

JW: The thinking is that high-waisted styles can make guys look taller by elongating the legs and promoting a streamlined appearance…

DH: Well I looked like Humpty Dumpty. But you liked the ones we tried?

JW: I did. My favorites were dark brown dress-pants by Suitsupply. When I wore them to dinner, my partner said I looked “very tall” and “like I’d been stretched.” I feel like there’s a compliment in there?

DH: “Stretched” makes me think of that bizarre elastic superhero, Mister Fantastic.

JW: I’ll take it. I admit I might be an ideal target for high pants because I have a weirdly long torso and stumpy legs. I disagree that these only work for skinny guys, but they are harder to wear than mid-rise pants. Dag Granath, from the cool Swedish tailoring brand Saman Amel, told me their proportions can be trickier for shorter or bigger guys. But I know guys with a range of body types who pull them off.

DH: Apart from the fact they lengthen your apparently miniature legs, why do you like these?

JW: They look much better with a blazer than lower-rise pants do, because when the jacket is buttoned you don’t get that horrible little triangle of shirt peeking above the pants. Also, I think a T-shirt tucked into high pants, with a longer overshirt or jacket open on top, is the ultimate easy, cool outfit.

DH: I tried that. It helped…a little. Until I turned sideways. Then I looked like Humpty Dumpty again.

Higher-waisted pants on recent runways at Todd Snyder (left) and Zegna

Higher-waisted pants on recent runways at Todd Snyder (left) and Zegna

JW: A longer jacket means the focus isn’t only on the waistline. But I’m not done selling these pants! I once asked Charlie Casely-Hayford, a stylish London tailor, what is the sexiest thing a man can wear. He shot back: high-waisted pants. They suggest a certain confidence—and can frame backsides well.

DH: You know who’s not sexy? Humpty Dumpty. No one is lusting after an anthropomorphic egg with balance issues. Also, it’s hard to look cool when you’re gasping for breath because your stomach is being compressed. All I could think was, “Is this what Cary Grant went through?”

JW: I can’t say any left me gasping, but they do put some pressure on the stomach, which can be an adjustment. If you use suspenders, they don’t need to be tight. Also, lots have elastic waists.

DH: When you said, “Why don’t you try an elasticized waistband?” what I heard was: “Why don’t you try an adult diaper?” It seemed like a sad concession to not being young and thin.

JW: Dale! Most brands these days sell stretch-waist pants, it’s just an acknowledgment that guys want comfort. Can you admit that high trousers are sexier than the pants that plague modern menswear: tight, below-the-hip styles that fall off backsides. Those never look good.

DH: Yeah, I don’t like super-low pants. I just like regular pants that sit at what I think is my natural waist?

JW: Nope, your natural waist is around the belly button, where high pants sit.

DH: Oh come on. That’s more like my unnatural waist.

JW: I’m sure lots of guys think the waist is at the hips—that’s how dominant hip-level pants have become.

DH: But, clearly, high pants were once the norm.

More recent examples from Tod’s (left) and Fendi

More recent examples from Tod’s (left) and Fendi

JW: Yep, from the 1920s pretty much through to the ’60s, when “hip-hugger” styles became a thing. Then, very broadly speaking, men’s pants went higher again for a couple of decades, before coming down in the late ’90s and 2000s. I believe you dabbled in high pants in your youth?

DH: Yeah, when I lived in London in the New Wave ’80s, I bought these super-high wool pants in a pattern the salesperson called “exploded houndstooth.” They sat on my rib cage. I thought they were so cool.

JW: They sound terrifying. But I’m happy to hear you’ve seen the light in the past.

DH: Well I thought of mine as stunt-y—I wore them to college lectures with a WW1 army helmet. Real cool. But I can see high pants look good on certain guys. What should the curious keep in mind?

JW: They can be hard to spot online because often brands don’t promote them as “high-waisted.” Look for descriptions like “sits on natural waist” or “higher rise” or “deeper rise.” And stick to straight or wide cuts—nothing slim.

DH: Also, if you have a bit of a stomach, you’ll need a bigger size than you would for lower-rise pants—which isn’t great for one’s self-esteem. I’ve got a new slogan for these brands: Our Pants Will Elegantly Ruin Your Day.

By Dale Hrabi and Jamie Waters

Nov. 1, 2024 12:30 pm ET, WSJ