How to Pinroll Jeans

Elegant gentlemen might not wear jeans very often, but when they do, a neat cuff at the bottom can help show off your socks and shoes while adding a touch of vintage-cool flair. In this article, we’re going to discuss the history of pin rolling your jeans and how to do it today.

History of Pinrolling Jeans

Initially called pegging, what we now know as pin rolling became very popular in the early 1950s with working class boys. Jeans were a functional work garment back then, and James Dean was the first to popularize them as a mainstream piece of attire in the movie “Rebel Without A Cause.” Due to their rebellious association, they became a statement for the youth who wore them.

Jeans were often inherited from older siblings or a family member, the hems were rolled or cuffed to fit their new, shorter owner.

Despite the rolling of sleeves becoming popular in the 1960s among suburban preppies, they avoided pin rolling jeans except when frolicking on the beach of Cape Cod or the Hamptons. It wasn’t until 1978 when the movie Grease came out that kids wanted to copy the style of John Travolta and the other T-Birds. Like Danny and Kenickie at Rydell, it became a trend for cliques of young boys and men to pin roll their jeans in similar fashion as a way of showing solidarity, similar to a uniform. Then in the 1980s and 90’s it soon became a stylish trend to show off the newest shoes that were popular at the time. Basketball shoes and other athletic sneakers were no longer just practical, but stylish amongst teenagers. Pinrolling jeans became a way to say “check out my new kicks” without actually saying it. High tops and other popular shoes could be shown off in an understated and more humble way over simply say “hey, look at these” and lifting the pant leg. Teenage idols like the New Kids on the Block began wearing pin rolled jeans as a fashion statement. Today, the trend continues for several reasons:

• To show off socks and shoes
• To make a jeans outfit more summery
• To shorten too-long jeans
• To create a more tapered leg shape

Like all style statements, there is a right way and a wrong way to do it and there are some style rules worth knowing.

How to Pinroll Your Jeans

Just as you would with rolling up your sleeves, it’s important to try and keep them looking neat. You don’t want them to look rolled (despite the name), but rather folded. Traditionally, pin rolling aims to makes the hem of the jeans narrower, since the tapered look is more flattering when jeans are shortened. However, you can alter the width of your jeans to your taste.

1. Choose a straight leg or narrow pair of jeans that will sit at about ankle height once rolled.
2. Put them on with your belt and shoes.
3. Bend over at the waist, trying to keep your legs as straight as possible. Locate the inside seam and pull the pant leg up to the narrowest part of your ankle.
4. Pinch the extra material vertically at the inside hem and fold it back tightly against the seam.
5. Holding the fold tight against your leg with one hand, roll the hem up to expose the inside of the jean and then use your other hand to fold the rest of the hem up a half inch.
6. Fold the hem up once again to secure the roll.
7.  Stand up straight again and look in the mirror to see the length. If it’s too long still, repeat the cuff technique until it looks good.
8. Once you have the perfect length, use it as a guide to recreate the same cuff on the other pant leg.
9. Look in the mirror to ensure the cuffs on both legs are even and not too bulky.

Do’s and Don’ts of Pinrolling Jeans

Do’s

1. Roll them at least twice to hide the hem within the cuff.
2. Pair pin rolled jeans with stylish shoes or boots.
3. Pin roll jeans to keep them from getting wet or dirty. It can help to protect your jeans from slush and snow in the winter or getting wet during a rain storm.
4. Pin roll your jeans to create new looks if you only own a few pairs. This way you can look like you’re wearing a completely different pair of jeans with something as simple as a cuff.

Don’ts

1. Don’t pin roll jeans that aren’t stylish. Dad jeans or work jeans that aren’t stylish uncuffed, won’t look much better with a cuff.
2. Don’t pin roll your jeans unless you’re wearing shoes worth seeing.
3. Don’t pin roll other trousers except for chinos. These are pretty well denim-exclusive.
4. Don’t pin roll super skinny jeans or baggy jeans. They will never look good.
5. Don’t make the cuff too big or small. 1-2 inches is perfect. No more, no less.
6. Don’t pin roll your jeans if they are too short or overly long. If they’re too short, they won’t roll properly and if they’re too long, they will puff out above the pin roll. Although a pin roll can hide a slightly longer jean that hasn’t been altered, it’s still best to chose jeans that are already the right length for you to wear. The pin roll will shorten them to about ankle height.

What to Wear it With

We never recommend sandals or athletic shoes for anything beyond athletics, so skip these entirely with pinrolled jeans. Here are some ideas on what kinds of shoes to wear pin rolled jeans with.

• Boat shoes and driving mocs without socks. Invisible liners are a great option for those preferring to wear socks.
• Loafers without visible socks.
• Leather or suede boots such as chukka boots, balmoral boots and chelsea boots with bold, colourful shoelaces.
• Casual leather, canvas or suede sneakers without socks or with invisible ankle socks.

Socks with Pinrolled Jeans

Unless you know all the rules and can now break them, go barefoot with pin rolled jeans. Sure, going barefoot isn’t something we often suggest, but pairing great, low-cut, summer shoes, with pin rolled jeans and the wrong socks looks about as bad as it can get. Avoid white sport socks, black, brown, beige, grey, navy and overly bold socks. Poorly constructed socks that will also droop and look unsightly.

If you are going to wear socks that will be visible, make sure you’re wearing bold, yet understated socks that are well made and won’t slink down to your ankles. Avoid ankle socks that show a gap between the sock and your trouser and avoid basic colors that look bland in comparison to a bold shoe and cuff. Remember, a cuff draws people’s attention and becomes a focal point. Your sock needs to stand out enough that it’s noticed but not thought about. The response you want should be nothing more and nothing less than a quick thought of “hmm, nice socks” before the person’s mind drifts to how great your shoes are. Ideally, the socks should act like your belt and simply hold the outfit together.

If you do decide to wear boots, make sure the boots are high enough that  the cuff still drapes over the top of the boot. That or, if it’s a low cut boot, wear a sock that works harmoniously with it the same as you would with a shoe. Some suggestions for socks are:

• Dress socks in deep reds, bolder blues or with a subtle pattern such as a shadow stripe.
• Bolder calf or knee-length socks in burnt orange, mustard yellow or even a Fort Belvedere green.

Conclusion

Pin rolling jeans are an option for casual environments. A walk in the park, playing with the kids, date night at a lounge or a drink with friends at the pub. Do you wear jeans? If so, do you pin roll them and what do you wear them with?