Unless you’re completely unaware of any fashion developments in the last year or so, you might’ve noticed that rolling your pants up is all the rage right now. Be it jeans or chinos, creating a cuff that sits right above the ankle has become a mandatory procedure in the everyday routine of fashionable men.
There has been a lot of debate about the appropriate height and rolling techniques, but my advice is to do it your own way: you’re the one who has to feel good about it, so forget about third party’s opinions. I usually roll them 2 times, which places the bottom of the cuff right above my ankle: this gives it a nice visual aesthetic and a relaxed feel as well.
Besides the visual effect the cuff itself provides, the main reason behind it is all about fit: by creating a cuff you’re adding weight to the bottom of the pant which makes for a better draping.
This is easily stated in dressier versions such as slacks or suit pants: as the fabric is more flexible than the one used in jeans or chinos, the effect provided by cuffs is that more evident. Also, in these type of pants you can’t create a cuff by rolling them up, you must have them tailored and the cuff will be permanent (the normal cuff height is about 3 cm).
Another important subject, especially for dressier pants, is to aim for little to no break. The break is the horizontal crease created by your pants when they touch the shoe (this is more noticeable in uncuffed pants but also applies to cuffed). Thus, a full break will create a deep crease and cover most of your shoe (the pant will hit at the top of the sole), and a short break will have your pant hit at the top of your shoe, removing the crease and creating a continuous line for the eye which makes your look taller and slimmer. The short break is the standard for high end Italian suits and has become popular by the extreme interpretation of Thom Browne and his “high waters”. Also, a short break will keep your shoes showing, affecting their impact in the whole attire.
I’m not suggesting you to cuff every single one of your pants, but this is a great look to pull of sometimes and it’s versatile enough to fit different styles. Go for it!