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A Guide to Rolling Your Jeans

A Guide to Rolling Your Jeans

Most jeans come with very long inseams, which means 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

Cuffed dark denim jeans paired with brown leather boots for rugged men’s style.

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

Men’s rolled jeans styled with gray oxford shoes for a polished casual outfit.

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


THE SIMPLE CUFF

Light cuffed jeans paired with brown suede loafers for a relaxed, casual look.

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

Men’s white jeans styled with brown suede desert boots for a clean, modern look.

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

Close-up of frayed jeans and white sneakers styled for casual men’s fashion.

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.


STACKED

Men’s slim black jeans paired with black Chelsea boots for a sleek and modern look.

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

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