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It's often the simplest problems that are the trickiest to navigate when it comes to getting dressed. A perfect case in point of this is figuring out just what to do with the bottoms of your jeans. Rolling, and stacking are easy maneuvers to get the job done—in theory. But executing style moves is often easier said than done. Truth is there are more options for what kind of pants to wear, there are also more decisions to make today in terms of finessing the hem of your jeans the right way. Here, we've laid out everything you'd ever need to know about navigating the subject with your Comfort Craftsmen

Why Roll Jeans In The First Place?

There are several benefits to rolling jeans.

#1. Aesthetics

– It breaks up the flow from pant to shoe. If you have really long legs this can balance out your proportions.

– It shows off more of your boot. You can keep the visual length of your legs intact while showing details that otherwise would be covered up.

– It shows off the inside of your jeans. When the inner lining contrasts with the wash of your denim it can make a nice end point for the eyes to notice your boots. Or if you're wearing high-end selvedge denim, you can make sure everyone knows about it. (Selvedge denim is woven on an old-fashioned shuttle loom, creating distinctive edges that only show on the ‘wrong' side.)

#2. Avoid the tailor tax!

Don't want to get every pair of jeans you own tailored? Rolling is a quick way to taper the cuffs without having to take them to the tailor



Rolling is what most guys mean when they say ‘cuffing your jeans'. A rolled hem is one that's turned up twice. Never roll more than twice or you'll look like you have bagels on your legs.

Aim for a 1.5″ cuff – the key is making the first roll less than an inch. Make each roll slightly lopsided for a nonchalant look.

Up until the 1960s cuffing your jeans was the norm, as they only came in a few lengths – so this is a retro look.

What Type Of Jeans To Roll:

Jeans that are full or half break length make for easy cuffs.

Selvedge denim that you want to show off.

Slim fitting jeans – the cuff needs some friction with your legs to stay up.

Designer jeans – most designer jeans come with very long inseams, and getting them hemmed will cost more than normal slacks and is something most tailors won't attempt.


Pin Rolling

This is like a military shirt tuck for jean cuffs.

Put on some un-cuffed jeans and stand up straight.

Grab the inner seam at the bottom of one leg and pinch it.

You will then want to fold the fabric against your ankle so the fabric now overlaps.

You can now cuff the jean.


What Type Of Jeans To Pin Roll:

Slim fit – NOT classic or relaxed fit.

Jeans that taper at the ankle and are not too baggy above the knee



‘Stacking' means letting jeans fabric bunch up above your shoes. This used to be seen as lazy, but now the music industry has made it very fashion-forward. When you wear skinny jeans and high ankle boots there will be excess fabric around the ankle. Just let the excess fabric stack on top of itself and rock it! This only works if your jeans taper from the knee down to the ankle.

What Type Of Jeans To Stack:

Very slim to skinny jeans. I'm sorry – a stack still only works with uber-slim denim, so if that's not your speed it's best to leave this to those who embrace a pencil-thin leg.

Pre-washed jeans – raw denim is likely to rub indigo dye all over your shoes.


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