A Gentleman’s Guide to Finding the Perfect Jeans

Denim connoisseur Riccardo Dallai Jr., owner of the Newbury Street menswear staple Riccardi, shares a gentleman’s guide to finding the perfect pair of jeans this fall.


Photograph by Kelsey Cronin


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“You have to wear raw jeans for a very long time without cleaning them,” Dallai says. “They may feel like sandpaper when you buy them, but the oils of your skin will soften them over time.” Dior raw jeans, $610, Riccardi.


Black wax-coated denim offers a sleek, clean finish that works for the office or a night on the town. “It gives the effect of a dressier look,” Dallai says. Saint Laurent “D01” waxed stretch jeans, $475, Riccardi.


“I like well-produced distressed jeans. There has to be some thought put into it,” says Dallai, who recommends this pair for its well-sewn patches and strategically placed rips. Amiri leather-inset jeans, $995, Riccardi.


What to Look For

Dallai recommends seeking out selvage jeans, which are constructed using the raw outer edge (or self-edge) of the fabric. For the cleanest construction, he says, go with Japanese and Italian brands. And don’t forget to cuff the bottom to show off the outer tab of the selvage seams.

How to Find It

When it comes to shopping for jeans, don’t simply try and buy: Dallai advises that you “do the denim squat” in the dressing room to see how they stretch.

When to Buy It

“Buy jeans in the fall and wear them through the winter so you have a cool pair that’s broken in and not heavy for the summer,” Dallai says.


The cornerstone of a good fit, according to Dallai, is the yoke—the panel of fabric between the waistband and the tops of the back pockets. “It needs to dip in the right way so that it doesn’t leave you with a flap in the back,” he says. He also recommends taking long-term wear into consideration: “No matter what—no matter the fabric or the brand—the jeans will stretch out.” In order to get the perfect fit after a few wears, he steers men toward pairs that are a full size smaller than what they would normally wear.