How It Should Fit: Pleated Trousers

May 15th, 2015

Continuing with our “How it Should Fit” series, today we take a closer look at pleated trousers.

While flat fronts have been all the rage in menswear for the past decade or so, style-forward guys are starting to appreciate the added comfort and level of detail found with pleated trousers (especially as they get older and start to refine their fits away from the super skinny).

mensstylepleatedpants (1 of 2)

You can brush up on general trouser tailoring here.

The major difference with a pleated trouser is that it cannot be cut as slim as a flat front, especially through the hips and thighs. The key to an elegant looking pleated pant is having enough room through the upper leg to allow the pleat to drape smoothly and fall effortlessly into the front crease. If the pleats are pulling open while you’re in a standing resting state, then the trousers are too slim.

Traditionally pleated trousers are also higher waisted (longer rise) and cuffed at the hem for a medium to full break (although I still like mine slightly tapered from the knee down with a minimal break).

mensstylepleatedpants (2 of 2)

Pleats (whether they are single, double, triple, forward, backward, box, etc.) are used to make trousers more comfortable by providing more room through the hips and seat. As someone who often wears slim-cut flat-front trousers, I can safely say that pleats can make a major difference – especially in terms of roominess in the front pockets.

As pleats start to become more and more prominent in modern menswear, here are some properly-fitting examples from the AOS archives (notice the front drape, the room in the thighs, and the mature gentlemanly vibes).

As always, feel free to use the Style Guide to find more inspiration.

580 (1 of 1)

Mr. Ignacio Quiles



Mr. Natty Adams

Thanks, as always, for reading. 

Yours in style,

Dan Trepanier

Shop Custom Menswear Made in America


Take me to the Shop

  • Max BornInTheNineties

    ‘although I still like mine slightly tapered from the knee down with a minimal break’ – couldn’t agree more, I think the fuller thigh with the taper, no-break and cuffs is the best way to tailor pleated trousers. It looks far more attractive than that very baggy 1930s style you see a lot with pleats.

    It’s the way my great-grandfather wore his trousers and it’s the way I wear mine!

  • PeterK1

    I think pleated pants look best worn with a traditional length jacket. Too short and it looks unbalanced.

  • JoeFromTexas

    Brilliant idea for a how-it-should-fit. Great info. I still wonder why double reverse seems to be the standard for RTW? Are reverse vs. forward pleats just a matter of preference, or do they have functional differences? Is one easier to manufacture than the other (I would think so, given the prevalence of reverse pleats)? I like the look of forward pleats, especially single ones, but I don’t know where to get one other than having it custom made.

  • tommyjohn_45

    Can’t lie.. I have a pair of single pleats from H&M and they are far and away one of my most comfortable pair of pants. Ideal for fitting my massive cell phone without looking like I have an abnormal on my thigh. They are also tapered, which I love. Been searching high and low for similar pairs but haven’t had any luck. I will say, my wife isn’t a huge fan though, haha… She isn’t nearly as big of a fan of the ‘classic’ menswear look like I am :s.

  • TO

    I tried on doubled pleated pants like the ones here at Club Monaco that felt amazing to wear but looked ridiculous! Don’t know exactly why because these look very nice- it’s a shame if brands are going all the way towards multiple pleats without letting a single pleat have its moment, I would like to at least be able to try on some of those!

  • twotone

    Good article. In the top photo, the side tabs look too low on the waist band seam. They would look better a bit higher on the waist band. Better yet — go with Daks tops. Also, if your trousers have belt loops — wear a belt! Or, take the belt loops off. Just my two cents.

    • James Wong

      I can’t see any belt loops on the top photo?

      • PeterK1

        I think he’s talking about Natty and Ignacio. Their pants have belt loops.

  • Sky Seveni

    Hmmm… you look very happy in those pants, Dan… very happy.

    • James Wong


  • Juan Zara

    Double forward pleats are starting to become very popular among style-conscious men, although they have never lost their appeal over here in Italy.

    RTW abels like Belvest, Caruso, Isaia, Sartoria Partenopea (who also make suits and sport coats for other labels) have never stopped offering them, and as far as my experience goes, MTM and bespoke tailors have always recommended them for suits. There’s even a bespoke tailor in Naples called Ambrosi who exclusively makes trousers, and the signature cut is a high-waisted, double forward-pleated model, like the ones Sean Connery wore in the Bond movies of the 60s (although his were made in London, by Anthony Sinclair.)

    I’m actually not a big fan of pleats, but I reckon what’s most important is the rise. For pleated trousers especially, having them reach your ACTUAL waist (meaning they should sit on your belly button, or an inch below it at most,) is crucial. Mr. Quiles’s look most correct here, while Dan’s sit a little low for my liking, but that’s a problem with 99% of trousers nowadays, unless you get them bespoke or MTM and actually specify how long you want your rise.

    As a side note, love the unlined purple grenadine!

  • Matt

    Dan, what brand are those pants, Are they more of the AOS samples?

  • Miguel

    How about reverse pleats Dan, does the same principal apply?

    • Dan Trepanier


  • Ethan W.

    Just wondering, is Natty’s suit a belt
    back? A holy grail for the vintage community is a pleated patch pocket, belted back suit!

    I’m not sure if Against Nature does those kinds of details!

    • Dan Trepanier

      Knowing Natty, I would say yes…

  • Eric

    Hell, this coulda been a Who Wore It Best feature outright. While I generally despise patch pockets on the breast, Mr. Adams’ rig looks exceptional.

    Dan, what kind of tie is that purple grenadine?

    • Dan Trepanier

      The unlined grenadine tie was given to me be a friend a while back. It doesn’t have a label…good eye!