How to: Cuff
Saying the word cuff or cuffing might lead you into two parallel but completely different countries of fashion; with side eyes from jesters and peasants and admiration from Kings and Queens. However it's a topic that is often overlooked in menswear by the people who actually wear the clothes, YOU! A pant cuff can range from the classic inch to inch and a half cuff on dress and suit pants made popular in the 1920's, or the folding up of the hem of jeans and chinos to create a more mod look. While most people might perceive these to be more of an aesthetic preference, both cuffing methods have functional attributes.

In classic tailoring, a suit or dress pant is made streamlined with the thigh and waist measurements. In this instance the pant opening around the ankle is much wider than the wearer's ankle circumference. Suit or dress pants, usually constructed of relatively soft luxurious fabrics such as wool or silk, can have a ballooning' effect at the hem. The cuff, with an inch or an inch and a half of fabric rolled, stitched and
pressed helps to give weight to the dress pant; anchoring it to flow better. Designers are adding the folded hem style to denim and chinos. Although constructed of heavier fabric such as cotton, denim and chinos avail the cuff for a different purpose; protecting the pant hems.
Now let's do some work:
It is always a good idea to go for a pair of pants that are a little longer than normal, this will give you a chance to get them cut and hem into a cuff you can be proud of. To be on the safe side, I normally say at least 1 inch off from the base of your favorite shoe, this will be less of a break and your shoe will be more visible. If you're in a more fashion savvy space, go for gusto and take 2 — 3 inches off from the base of your shoe!
The Cuffed pants on the left have no break and show more shoe with a tad bit more sock or ankle if you're feeling daring. Cuffed pants with a medium to a full break cover the ankle and shoe fully, this is the most conservate of fashion trends.
Now when it comes to denim or chinos, cuffing takes a different and very important route for having crisp pant hems. The cuff on denim and chino style pants are there to primarily protect that finished crisp look. Cuffing takes on an even higher fashion calling.

On the left the 1 inch roll, works on any style of jeans or chinos and on the right the 1.5 - 2 inch roll (you should probably get your jeans shortened if they are this long), works better on slimmer styles of denim or chinos.
The thin roll, works best with lighter weight denim, great with lighter weight shoes, such as canvas slip-ons or chukka. On the right the double cuff (flip it up 2 times) works best on light to mid weight denim, great for basically any shoe or boots. Again be mindful as this cuff, like the 1.5 inch roll, can make you look shorter from the waist down.
Now have fun on your style journey!
Best,
C.R.