The debate over rules to roll up your jeans come with Oxford comma proportions. Should you roll up twice? Thrice? Wait, was it supposed to be one giant single fold so it looks like the uncoated end of a Pocky stick?

We pass the style judgement once and for all.


Just so you know why you’re really cuffing: To shorten/taper an otherwise long-ish/baggy pair of jeans, if not to add stylistic flair to your ankles.

Why you need know this piece of style wisdom: Because you saw all your friends do it and you want to follow suit. It’s a classic hallmark of Singapore fashion among men. Monkey see, monkey do. So here’s one universally good reason to be doing it for yourself. You want to be showing off the stylishness of your sneakers without drawing attention to the cuff itself. Or your lack of inches (in height). Or your ankle baring ineptitude.

Bonus: If you really want to impress people with your shit, tell them the true purpose is to subtly display the selvedge.

Selvedge: Coloured inseams that indicate premium denim.

How the man on the street (i.e. you) is screwing up: Rolling up too much (or what it’s called the Chunky Roll), rolling up too little (jean legs version of the Asian eyes slit), rolling up when there’s not much of a need to roll up (‘cos it’s so loose fitting cuffing can’t save it) and unevenness of the fold.

Do you even need to cuff: Not when your pants are already pre-cuffed, duh. But let’s say if you’re already wearing tapered jeans with high cut sneakers, let it stack on top of your shoes naturally.

Can you work this on other kinds of full-length pants: If you have to. And hopefully it’s not the Dad fit kind.


What the internet says

The pinroll

A style parlour trick to taper slim or straight fit jeans/pants so the cuff wraps snugly around your ankles. No pins needed.

How to do it:

Step 1: Pinch the hem outwards against your ankle until it’s snug.
Step 2: Fold the denim onto itself.
Step 3: Roll up twice while pinching the hem. Even out the pin roll if it bulges out too much.

What Seriously Man says

The double roll is still the classic move to roll with. It’s the safe bet for most pants style to highlight a sick pair of loafers or high tops, and it’s the OG of cuffing.

Remember this magic number: 4cm. Because that’s the ideal length of a cuff in our style bible, give or take ±0.25cm.

How to do it:

Step 0.
Step 1: Make your first fold up. A good 4cm to 4.5cm (or slightly less than 2 inches) should suffice.
Repeat step 1. Smoothen and neaten the double roll wherever necessary. Simply pinch around the inside and outside of the fold and roll down if you feel like you went up a little too much.