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How to buy men’s jeans: ‘The perfect pair can be your favourite garment for decades’

May 18, 2023

From rear-flattering fits to choosing the hardest-wearing fabric, menswear experts share their secrets for good jeans

Invented in 1873, denim jeans have remained pretty consistently in style ever since. When Levi Strauss patented the metal rivets on his workman pants to make them more durable, he could not have predicted the hold they would have on the fashion industry for the next 150 years.

This week, four fashion insiders tell us what they look for in men’s jeans. Perhaps unsurprisingly, their desires haven’t strayed too far from the original Levi’s 501.

When writer and editor Mitch Parker was living on campus at university, he saved up for a pair of Ksubi (or as the brand was known then, Tsubi) skinny jeans. They were so precious to him, he’d sit for hours watching them dry on the communal washing line every laundry day, because he was scared they’d get stolen.

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Now he believes the greatest jeans in history are Levi’s 501s. “They’re everything a pair of jeans should be,” he says.

Because “denim is one of the most hard wearing fabrics in existence, that gets better over time,” he recommends hunting down vintage pairs. “I’ll also stick with more traditional colours like black, indigo and stonewash.”

Getting the right fit in a vintage pair of jeans can be tricky, so Parker always enlists the expertise of a tailor. “Every single pair of jeans I own, I’ve had altered in some way, whether that’s the leg shortened or narrowed or the waist taken in slightly.

“Trust me, it’s the best way to get your jeans to fit perfectly and to have people compliment your butt.”

He’ll also “never, and I mean never, buy a pair of jeans that come pre-distressed”.

“I have a pair of vintage selvedge 501 XX’s that must be over 40 years old,” says Ivan Budah, the designer behind Larriet, a menswear brand launching in August.

“They’ve also built up a pretty serious dirty wash appearance over the years that simply couldn’t be replicated.”

If a worn-in patina is what you’re after, he suggests Levi’s Vintage Clothing jeans.

For new jeans he recommends denim by Japanese labels orSlow and Kapital. “Denim can be a massive rabbit hole and I feel that there are some green flags to look out for … I think it’s safe to say if it’s Japanese you’re in good hands,” he says.

But finding the right fit can still be difficult, so he always has “some crucial measurements” on hand, especially when he’s online shopping.

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He suggests taking the measurements of your current favourite jeans at the waist, inseam (from crotch to hem), rise (the distance between the crotch and waistband) and leg opening (the width at the bottom of the pant leg), then comparing to replicate the fit.

Stylist Thomas Townsend describes finding a good pair of jeans as “one of the hardest things you will go through in life”. So, when he finds a good cut, he buys it in as many washes as possible.

His favourite jean is the 1991 by Swedish label Acne – it has a relaxed, straight silhouette. “As someone who has lived through the ‘skinny jean’ movement of the mid-00’s I’ve sworn no matter the trend I’m not going back,” he says.

He looks for high-quality denim made from 100% cotton in a heavier weight that is coarse, stiff and rigid. “I enjoy the idea of really living in your jeans, staining them, having them repaired and watching them patina over time.”

While it’s tempting to buy new jeans with elastane in them, because they feel softer on the body, he says you should avoid this because elastane compromises durability. Rigid denim will naturally soften and stretch once you start to wear it, and it will last much longer than something with a high elastane content.

Melbourne designer Christian Kimber is on a jeans-inspired mission. “When you find the perfect pair, they can be your favourite garment for decades,” he says.

The best jeans he ever owned were Levi’s 501s. “Mine lasted for about ten years, wearing in really well over time,” he says. But he’s struggled to find modern denim that gets the balance of form and function right. This led him to develop his own jeans.

He prefers a classic fit, with a light taper in the lower leg, a slightly higher rise and a bit more room in the seat so that it doesn’t feel constricting. A good pair of jeans shouldn’t limit your activities, he says, “whether that’s walking the dog, being on a plane, going out for a bite, or lounging around the house”.

How well jeans wear over time comes down to the materials and construction. “I look for a heavier weight denim, ours are 31.5oz, so they’re not only warmer but won’t tear a year in, double stitching and high-quality buttons, zips and rivets.”

Jeans should be as versatile as possible so they can be styled up or down. He avoids artificial distress, marks, overt branding and stand-out stitching. As for length: “I like my denim to touch my heel, so I have the option to wear classic or roll the cuff depending on how I style my outfit that day.”

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