To cuff or not to cuff? That’s the big question. Cuffing your pants is one of the best ways to show off men’s shoes, but it’s a bit of a minefield. The wrong cuff with the wrong jeans can make you look heavy, short, or just plain weird. Some guys cuff too high and look like they’re about to Hulk right out of their pants. Others let the fabric flap around their ankles, which hasn’t really been a good idea since 1997. And then there are the different kinds of cuffs: pin-roll cuffs, single and double cuffs, deep cuffs, skinny leg stacks, the list goes on and on.

Today we’re breaking down the common cuffs for men’s shoes and men’s boots, and giving you some simple style advice. Remember, we’ve suggested one cuff for each shoe below, but that’s not a hard-and-fast rule. Chelsea boots, for example, can work with a double cuff, cropped hems, or a stack. Play around until you find something that feels good to you.

This is Aquila’s guide on how to cuff jeans.

There are a few reasons you might want to cuff your jeans. The first is obvious: it draws attention to your shoes. Cuffing creates a neat hemline, usually high above the shoe itself, so people can get an eyeful of that Italian leather upper. If you have really long legs, cuffing can also balance out your proportions and break up the flow. Finally, cuffing shows off the inside weave of your jeans. Most guys won’t think too much about that one, but if you’ve gone to the trouble of wearing something like selvedge denim (which is woven on an old-fashioned shuttle loom) you want people to know about it.  

Rowan Tan Casual Shoes

Chelsea boots are close-fitting, ankle-high boots with an elasticated side panel. They’re arguably the most versatile boot on the planet, able to go from weekend casual all the way to corporate suit and tie, and they tend to look best when cuffed. For Chelsea boots, you generally want a strong double cuff (although, as mentioned above, stacks and cropped hems can both work with the right jeans).

How to double cuff
1. Roll your hem over once to create a cuff about 1 to 1.5 inches wide.
2. Roll the cuff over once more.
3. Straighten the cuff and make sure it’s even.
4. Keep the hemline an inch or so above your ankle.

Osbourne Oxblood Chelsea Boots

For low-top sneakers, we like a clean, high pin-roll cuff. This cuff works well with jeans or chinos, and it shows off plenty of ankle (you can either wear invisible socks, to flash some skin, or lean into the retro trend with colourful crew socks). The pin-roll cuff is one of the higher cuffs, and it hugs your leg quite tightly.

How to pin-roll cuff
1. Pinch your hem horizontally, so the jeans feel snug against your ankle.
2. Take that loose fabric between your fingers and fold it backwards.
3. Now roll the cuff twice over, about 1 to 2 inches.
4. The hem should sit quite high, about 1.5 inches above your ankle.

Military boots are quite heavy on your feet, so you need a cuff that balances things out. Depending on your jeans, that’s going to be a double cuff or a simple stack. For straighter leg jeans, go the double (you probably won’t clear the entire military boot, especially if they’re high-tops, but that’s totally fine). For slim-fit jeans, simply let the fabric bunch naturally at the top of the boot. That’s called a stack. It works best with chunky military boots.

How to stack
1. Pull on your boots.
2. Adjust the hem so it falls naturally at the top of the shoe.
3. The fabric should bunch around your ankle.
4. If it’s too loose or heavy, consider a double cuff instead.

Ingram Black Military Boots

When you’re wearing Oxford or Derbies with suit pants, you should hem the pants so that the fabric just rests on top of the shoe, creating a gentle fold. That’s called a natural ‘break’, and it’s still a pretty good rule with jeans and chinos. A tailored hem is going to be the most formal and conservative approach for dress shoes. But it’s not the only way to go. Some Oxblood leather Derbies with slim-fit jeans and a single cuff can look good, as can loafers with chinos.

How to hem your pants
1. Take your suit pants to a tailor.
2. Get them measured and fitted properly.
3. Hem the pants so that the fabric rests on top of your shoe.
4. Watch for that natural ‘break’ or fold. That’s the sweet spot.

Alberto Cognac Loafers

Chukka boots and desert boots look great with all sorts of cuffs, to be honest. Stacked slim-fit jeans with tan desert boots is a great weekend casual look. A high, pin-roll cuff over some suede Chukkas can also work nicely. But most of the time, you can get away with a simple single cuff. Just roll your hemline once over, about 1-1.5 inches, until it rests alongside your ankle bone. This will add some definition to your Chukka boots (without bulking out the pants too much).

How to single cuff
1. Take your hemline and fold it upwards once.
2. The cuff should be about 1 to 1.5 inches wide.
3. Straighten and adjust the cuff to keep it neat.

• Remember, the thicker and higher the cuffs, the shorter and heavier you’re going to look. If you want to stretch out your leg, go for something like stacked slim-fit jeans.
• Avoid chunkier cuff styles with heavy, straight leg jeans. There’s too much fabric, and it’ll bunch around your ankles. Stick to hems or single cuffs for those guys.
• Give some thought to the ‘weight’ of your shoes. Military boots, for example, are quite chunky, so they’ll throw skinny jeans way off balance. Heavy shoes, heavy cuffs.
• The measurements above are just guidelines, and every guy will be slightly different. The type of jeans, your height, leg shape, shoe choice, personal style—they all affect the width of your cuffs. Play around until you find something you think looks good.