A Guide to Rolling Your Jeans

April 3rd, 2015

Most jeans come with very long inseams, which mens you have to make a decision about how you’re going to wear them. There are several different ways to treat the hemline, each of which creates its own look and is best combined with certain fits, types of denim, and overall aesthetics.

Here’s a quick guide to some options that we recommend.

The Clean Fold


Sharp, strong, clean. Best for long jeans, crisp heavy denim, chunky footwear, and larger guys who need a lighter weight to anchor them down.

The Sloppy Roll


Laidback, nonchalant, imperfect. Best for lightweight tapered denim and casual outfits that are thoughtfully put together but purposefully unkept.

The Simple Cuff


Smart, easy, no-fuss. Best for simple outfits, straight leg jeans, a proper fitting inseam, and guys who aren’t too “fashion-y” but care about details.

The Cropped Hem


Best for slim tapered denim, minimalist dressers, tailoring aficionados, shorter guys, and dressy outfits that incorporate a tailored jacket. Usually reserved for warmer climates to let the ankles breathe.

The Cut-Offs


Best for broken-in washed jeans, bohemian vintage wearers, the hipster DIY crowd, and rugged looks incorporated worn-in garments. Also usually more natural during the Spring/Summer.



Best for black or very dark skinny jeans, long and lean guys, rock & roll inspired looks, and late at night with with a sleek boot and leather jacket.

How do you wear your jeans? Use the comments below to share!

Thanks, as always, for reading.

Yours in style,

Dan Trepanier

Shop Custom Menswear Made in America


Take me to the Shop

  • O.

    Hi Dan,
    Just a quick question… I am wondering what rise you typically wear on your jeans / chinos? I am tall (6,1) and slim guy. Recently I realized that all the chinos / jeans I have sit rather low (think hipbones) and the tucked in shirt looks a little bit unsightly.
    I think going with s slightly higher rise might be better, but on the other hand I do not want to look like and old man… Can you help out?


  • Ryan

    I’m going with the cut-off this summer… when summer in Canada arrives!

  • Jack

    Where are the shoes in “The Clean Fold” pic from?

    • TR

      AE Eagle County

      • Jack


  • James Wong

    I almost exclusively use “the clean fold”, however I vary the number of folds depending on what shoes I’m wearing and also the weather. For example, most shoes take a double fold, however my loafers look best with just a single, otherwise it exposes too much ‘foot’. If I’m in a hot climate, I sometimes go triple or quad fold with no socks.

    I think it’s worth nothing that the thickness of the fold is important, with it being about an inch wide in my opinion. Of course many people break this rule for their own style too.

    Who knew I could write so much about jeans folds!

  • Sky Seveni

    Any tips for men with thin ankles? I have somewhat muscular thighs but they taper down to an ankle thin enough to almost encircle with my thumb and middle finger. This makes things a little flappy down there unless the taper is quite narrow. Also, it’s harder to look balanced in chunky shoes or boots.

    • Stuart

      Try pegging them. You just have to be careful that the leg hole isn’t too wide, otherwise they’ll look odd and poofy.

    • ChrisD

      I experience the same thing. Took many iterations (buying jeans and/or having them tapered) before i found a good balance. In the end I retired some chunky shoes which fit a little big anyway, and own some sleek boots which look more natural under heavy taper.
      I also employ the “clean fold” example in this post – my inseam is about 32” but wear super long denim (36”+) and roll a couple times – gives some girth which looks better over boots.

  • David_Mtl

    What boots are in the first shot?

  • Brent

    Puddling effect??? Really! Come on guys you are in the fashion game it’s known as “stacking”

    • http://www.TSBmen.com/ Dan Trepanier

      Good call.

  • tommyjohn_45

    I tend to stick with the clean fold.

    Anyone on here from or familiar with MTL? If so, can you recommend any go-to places for clothing? thanks

  • cam

    where I live, everyone wears jeans…everyone. it’s almost like no one owns anything else. because of this, I rarely wear jeans anymore and opt for mostly cords in the f/w and chinos in the s/s. the cords are usually worn with boots so I get the puddle effect and chinos are hemmed to no break.

  • TO

    I have most often opted for the cropped hem in the past, not actually cropped on boots like pictures, but a clean hem for shoes, sneakers. One of the problems is that the height of different dress shoes v. sneakers v. loafers make this approach to a hem inconsistent in terms of tryin to achieve a consistent look. Now I’m leaning more towards a slightly longer hem so I can simple cuff when necessary such as with higher cut shoes, crop hem with loafers (or simple cuff), a bigger simple cuff with boots or a clean fold. It gives a lot more options and I’ll do it with the New Standards I’m breaking in currently.

    You should make a section on the header for “Guides”- the simple straightforward guides that have come out since the changeover are probably my favorite part of Articles of Style so far!

  • Miguel

    Nowadays I don’t the cutoff and pudding, back in the days I used pudding a lot, cutoff were a time fashion thing, I don’t see it that often anymore.

    • cam

      which flavor? chocolate or vanilla?

      • Max BornInTheNineties

        I usually go with strawberry. (Only when I’m wearing selvedge though.)

  • Jeanscuffed

    It’s safe to say that I try all of these except the cutoff. I found a jean that’s broken in but I’m not ready to cut the hem lol. I noticed that a while back you mentioned puddling is something you try to avoid because it looks sloppy and doesn’t emit a well put outfit. Looking at this post, I assume back then you were talking about the pants/jeans not being tailored at all with the puddling effect. Great post, although since I’m addicted to full outfits you give your readers, it would have been awesome to see the full outfits along with the pictures shown here to convey the full vision of what goes with what.

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