Back to Basics

Return to
the Fold

Back to Basics

Return to
the Fold

The coolest chinos are pleated, roomy and ready to be worn everywhere

Best men's pleated chinos in 2023

This fall, menswear is going back to the basics. There's a real return to dressing up, with a revival of workwear and neo-preppy classics. That means the classics are cooler than ever and are being refreshed by brands both big and small. And we're celebrating that return. Starting off with the pleated chino—an essential part of a man's wardrobe, especially come fall. Comfortable, versatile and practical, you might think of these khaki cotton pants as simple office wear, but the chino got its start, like so many icons of menswear, with the military.

In the 1840s, British colonial soldiers marching through India dyed their white uniforms to match the terrain's dusty, saffron-hued sand. In fact, the term khaki is derived from the Hindi word khak, meaning “dust-colored”. Eventually, every soldier was outfitted in khaki cotton uniforms and soon they became standard-issue for many of the world's military. But it was young American soldiers who introduced the pant to civilians—sporting their uniform chinos on college campuses after returning from World War II.

Why This
Works Now

Put simply, it just looks fresh. With a sea of flat-front chinos still walking around out there, these fuller-cut, pleated styles give you a leg up while giving you plenty of leg room. If you haven't tried out a wide-leg style yet, pull on a pair and revel in the comfort, and notice how the extra room allows your phone to rest more comfortably in your pocket.

They were durable and as easy to wear as they were to clean. Cut from cotton twill, the pants were more respectable than a pair of jeans but not regarded as stuffy. If denim was becoming a symbol of mid-century rebel youth culture, then chinos represented an optimistic, educated gentleman. Along with horn-rimmed glasses, oxford button-downs and penny loafers, a pair of crisp chinos completed a collegiate style tied to the Ivy Look.

Since then, chinos have become a cornerstone of an American man's casual wardrobe. They were spotted on Hollywood legends, seen in countless Ralph Lauren collections, and on the cover of early J.Crew catalogs. The shape and silhouette continued to adapt to the times. While pleated chinos were at first a weapon against the suit-and-tie conformity of corporate America, they eventually suffered the same fate during the “casual Friday” boom in the '90s. But you can't keep a good pant down. Those ill-fitting workaday khakis gave way to more tailored flat-front styles in the early aughts. Chinos seemed to trim down until they couldn't get any slimmer and, like everything in fashion, were rife for reinvention. After a decade of tighter styles, pants started widening over the past few years and pleats slowly started popping back up. Now, a pair of pleated chinos proves more is more while pulling double duty—it's at once classic and yet thoroughly modern.

Why This
Works Now

Put simply, it just looks fresh. With a sea of flat-front chinos still walking around out there, these fuller-cut, pleated styles give you a leg up while giving you plenty of leg room. If you haven't tried out a wide-leg style yet, pull on a pair and revel in the comfort, and notice how the extra room allows your phone to rest more comfortably in your pocket.



What to
Look For

Men's pleated chino detail



The Pleats

Single or double? It's a matter of taste and how much fabric you're comfortable with. They also fall into two categories, forward and reverse. Forward pleats open towards the trousers' fly (and are associated with English tailoring). Reverse pleats open outwards towards the pockets (and are associated with Italian tailoring).

Men's pleated chino cuff and crease detail


& Cuffs

Cuffs & Creases

If you want these to feel a little more dressy, these details like permanently pressed creases down the legs or cuffs at the ankles add a little formality. Of course, you can do this yourself with an iron, too.

Men's pleated chino button detail



The Buttons

Whether it's just at the waist or down the fly, as well, make sure that the buttons are solid and well-stitched. They don't have to be horn or natural nut material, though some are.

Men's pleated chino pocket detail



The Pockets

Most chinos will have besom pockets. These are the ones that are cut into a garment, rather than being sewn on. And they typically have reinforced edging along the opening. Some will have flaps.

Men's pleated chino extra trims detail



Extra Trims

These are the pieces that make a pair stand out. It could be a unique pocket or stitching. It might be old-school details like side waist adjuster buckles or a tab waistband.

The Best Pleated Chinos
in 2023


An update on an archival design with a relaxed fit, subtle single pleats and a full leg.

Relaxed-fit pleated chino,
$98 by J.Crew

Bronson Mfg. Co. Ivy Style pleated chino

An old-school chino with double pleats and slash rear pockets. Finished with wide hems to cuff and natural corozo buttons.

Ivy Style pleated chino,
$39.99 by Bronson Mfg. Co.

COS Tapered pleated chino

This pair is cut with a lower waist and a slimmer, tapered leg. It's finished with subtle single pleats and cuffs can be rolled up or down.

Tapered pleated chino,
$120 by COS

Beams Plus Pleated twill chino

Inspired by a vintage pair of chinos, these Japanese-made pants are cut from a soft washed cotton in a loose fit with double pleats.

Pleated twill chino,
$149.95 by Beams Plus

Alex Mill Standard pleated chino

Like the Beams Plus pair, these have a small flap coin pocket at the waist. But these also have a more modern cut with single pleats.

Standard pleated chino,
$135 by Alex Mill

Ralph Lauren Whitman relaxed-fit chino

Based on a classic pair of Polo trousers, these chinos have a relaxed silhouette. The double pleats are accented by a traditional coin pocket at the hip.

Whitman relaxed-fit chino,
$168 by Ralph Lauren

Everlane Tapered pleated organic cotton chino

A no-nonsense pair cut from smooth cotton with a touch of stretch. The single pleats highlight the subtle permacrease down the tapered leg.

Tapered pleated
organic cotton chino,
$108 / $81 by Everlane

FrizmWORKS Hawthorne one-tuck pant

These are cut from a high-density cotton chino fabric for added durability with a loose, tapered fit. They're finished with natural nut buttons.

Hawthorne one-tuck pant,
$105 by FrizmWORKS


Investment Pieces

With a generous straight-leg fit, these chinos are made from a cotton-gabardine fabric with a slight sheen. The double pleats accent the permacrease down the leg.

Cotton gabardine chino,
$235 by Wacko Maria

Noah Twill double-pleat chino

Noah's take on the classic chinos are made in Portugal from a washed cotton twill. They're double-pleated with side seam besom back pockets.

Twill double-pleat chino,
$228 by Noah

Universal Works Twill double-pleat chino

Double pleated, with a loose straight leg, these chinos have been cleverly cut with no side seams to give a full, flattering leg shape.

Twill double-pleat chino,
$211 by Universal Works

Ghiaia Marinaio double-pleat chino

These luxe cotton twill chinos have been cut in a high waist silhouette and finished with double pleats. Made in Italy, they're finished with genuine horn buttons.

Marinaio double-pleat chino,
$495 by Ghiaia

Barena Cotton gabardine chino

Another high-waisted, double-pleated pair. This one is cut from a garment-dyed stretch cotton gabardine.

Cotton gabardine chino,
$370 by Barena

Drake's Single-pleat chino

Drake's “house style” chino has a mid-rise waist with a tabbed waistband, single pleats for greater freedom of movement and a gentle taper below the knee.

Single-pleat chino,
$595 by Drake's

Rubato Tab-waist dress chino

Made from mid-weight, high-density cotton twill, these are finished with a single reverse pleat and a full, straight leg. They're delivered unhemmed so you can choose if you want them with or without turn-ups.

Tab-waist dress chino,
$335 by Rubato

Officine Generale Hugo chino

These garment-washed chinos have a subtle, single pleat and substantial cuffs. It comes with a removable self fabric belt.

Hugo chino,
$370 by Officine Générale

Norse Projects Gabardine chino

These relaxed chinos are tailored from a premium high twist Italian twill and finished with back flap pockets, refined internal detailing and a French bearer fly.

Gabardine chino,
$295 by Norse Projects

Get the
Fit Right

Brian Davis of Wooden Sleepers

Vintage dealer Brian Davis of Wooden Sleepers knows his way around the racks and is here to help you get the right fit for your body type.

Pleated chino fit illustration

One knock against pleats is that since the folds create excess fabric, it can visually widen the hips. If you're concerned about too much bagginess, Davis says find “less extreme” options. For instance, larger guys might want to stick to single pleats. Similarly, while chinos look great cuffed, shorter gents should be warned: Wide cuffs can make legs look shorter.

Pleated chino fit illustration
Pleated chino outfit illustration

And remember: “It's not just about the pants, it's the whole fit, so ideally you find something that works within your existing wardrobe. You have to be open to experimenting.” Vintage styles are a great way to find a pair to try out while keeping costs low.

How to

Casual pleated chinos outfit


Fleece crewneck, $99 by Patagonia

Braided leather belt, $70 by Nisolo

Canvas Legend sneakers, $85 by SeaVees

Classic pleated chinos outfit


Wool cardigan, $285 by Folk

Cotton waffle socks, $20 by American Trench

1936 Larson loafers, $175 by G.H. Bass

Dressy pleated chinos outfit

Dressed Up

Oxford button-down, $$89.50 by J.Crew

Dress belt, $148 by Todd Snyder

Leather derby, $400 by Mr P.

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