The Most Stylish Men’s Pleated Pants for Every Occasion

Pleated pants may not be the first thing you think of when it comes to earning style points, but the professor-approved bottoms are arguably one of the most elegant things you can wear on a daily basis. Whether it’s due to a demand for more comfortable formalwear or the inability to deny how lavish they look, pleated pants are back, and they’re here to stay — as a matter of fact, some would argue that they never even left.

Time and time again, it’s been proven that staying comfortable and looking stylish can’t coincide, and this well-aged garment is practically walking proof of that — at least once you throw a pair on, anyway. Seeing as the definition of pleats often gets misconstrued, and each brand seems to have its take on the matter, we’ve narrowed down the method’s true meaning and even compiled a guide to the best pairs of men’s pleated pants.

What Is a Pleat?

Pleats come to shape when clothesmakers gather multiple folds of fabric and sew them into the garment to add more volume, secureness, and style. Ever since their conception (as we know them to be) in the 1920s, the fashion-forward method has been trendy, mundane, and then trendy again, only to be recognized as one of the more common styles in formal attire.

Pleated pants provide much more freedom of movement than your average bottoms, as they provide extra room in the thigh and leg area that will ultimately lessen creasing. In contrast to flat-front trousers, pleats are noticeable in the rise of the pants and provide a flowing, luxurious look to them. That’s not to say the average pair of pants can’t be as stylish, but it’s hard to compete with traditional pleats. With that in mind, take a look at which silhouette suits you best in our collection of pleated pants.

Casual Vs. Formal Pleated Pants

Pleats have been coming back in style in the menswear space (both casual and formal), and much like workwear gear, pleated pants are receiving modern designs with a new set of eyes. If you want a casual look, a pair of pants with belt loops like chinos is a perfect choice, and a double-pleated pair with a high waist will give you that formal style.

What to Look For

Material: You really want to choose your pant material based on your preferred style and time of the year. The most common materials will be wool, cotton, and linen, and something like linen, for example, will be better in the summer, and wool will be better in the winter.

Fit: You know the drill with pants – they’ll usually come in slim, regular, or relaxed fits, and you should know how each style fits your body and overall wardrobe.

Pleats: Pleats will vary in depth and amount, with double pleats giving you a more classic look and single pleats providing a modern one. As for depth, deeper pleats will be more noticeable, and shallow pleats will be more subdued.

Length: For a safe, classic look, go for a pair of pants that’s slightly tapered. Other than that, just make sure the pants are tailored to your height (or hemmed).

Wax London Pleat Trousers Black Cotton Twill

Best Starter Pants: Like most things from Wax London, these trousers are the perfect blend of formal and casual. They are primarily made of sustainable cotton but feature a touch of elastane to give them the perfect amount of stretchiness. As an added showcase of the boutique’s eco-cognizance, it implemented corozo nut buttons as opposed to the standard use of plastic, which is a far more responsible alternative.

Carhartt WIP Colston Pleated Stone-Washed Cotton-Twill Trousers

Best Soft Pants: Carhartt is a great brand to consider if you want a pair that you can dress up or down. The heritage workwear label rounds its pleated bottoms out with a stone-washed finish, resulting in a unique fade and a super soft feel right out of the box. More importantly, they’re crafted from a warm blend of cotton, making them easy enough to toss on with ease and cozy enough there all autumn long.

Taylor Stitch The Matlow Straight Leg Single Pleat Pant

Best Organic Cotton Pants: Like anything remotely formal from Tayor Stitch, the Cali-based menswear label’s pleated chinos are hard to overlook. The pants are crafted using nothing but organic cotton, and feature a pigment-dyed herringbone finish to give you that vintage look. Although these are inspired by the ’50s, you get a modern look with the single front pleat.

Alex Mill Keaton Double Pleat Pant in Twill

Best Lightweight Pants: Alex Mill may have gotten its start trying to perfect shirts, but through that journey, the label figured out how to perfect essentials. These double-pleated pants are certainly essential, too, and are made with a cotton/lyocell blend to give you some moisture-wicking utility and a soft feel. They have a classic look with a high-waist fit and double pleats, but you could easily wear them in a more casual outfit.

Noah Twill Double-Pleat Pant

Best Double-Pleat Pants: Noah’s fluid blend of traditional streetwear and preppy formal attire always churns out a trusty look, and the Twill Double-Pleat Pant is no different. The brand’s take on the quintessential pants is made with 100% cotton twill that’s built to last and retain its shape over time. They are available in a utilitarian shade of beige and black, or green and blue if you want more color.

Knickerbocker Corduroy Town Pant

Best Corduroy Pants: As its name entails, Knickerbocker is based in New York, and these flowing bottoms are versatile enough to rock on any street in the Big Apple — or anywhere else, for that matter. They have a 100% cotton corduroy makeup woven by Duca Visconti in Italy that has a sturdy structure and fits like a charm. Lastly, the pants are rounded out with a traditional four-pocket styling and talon zipper fly.

Todd Snyder Relaxed Pleated Work Pant

Best Relaxed-Fit Pants: Like anything from Todd Snyder, these workwear-inspired pants embrace the timeless elements of menswear. They’re inspired by vintage work pants down to the unique handful and even feature double knees and a tool pocket for added utility. For the sake of style and comfort, they’re single-pleated, deeming them even roomier than the standard pair of pleated pants. Most importantly, they are durable enough to help you comfortably tackle the cold weather.

Drake’s Grey Wool Flannel Single Pleat Trouser

Best Wool Pants: When it comes to formalwear, Drake’s is one of the key brands to keep an eye out for — at least if you’re willing to pay top dollar. The premium brand’s Italian-made Grey Wool Flannel Single Pleat Trousers are cut from soft wool and finished with single front pleats. Ideally, this is the perfect pair to wear if you have a blazer to match, but they will work just fine on their own.

The Wardrobe Essentials Every Man Should Have

For more versatile menswear, check out our guide to the best wardrobe essentials for men.