Turnup for What? 
If you ever find yourself waffling on whether or not you should cuff your trousers, Jesse has a great guide here that he wrote a few years ago. As he noted, cuffs are largely a matter of personal taste, although there are some general guidelines that can be good to follow. Pleated trousers, for example, almost cry out for cuffs, while flat fronts can go either way. And while you can more or less cuff anything, you’ll want to leave them off formal trousers (i.e. black tie pants) and perhaps your most casual (e.g. you can cuff your “dress chinos,” but you might want to leave them off the run-of-the-mill variety).
If you’re still left undecided, then here are two more useful guidelines.
Cuff everything. The reason is simple. You can always remove cuffs from trousers, but you can’t always put them in (depending on how your tailor has hemmed your pants). So unless you’re absolutely positive you want plain hems, err on the side of caution and request cuffs. You can get rid of them later if you decide you don’t like them.   
Think of typography. StyleForum member Parker (who’s day job is in graphic design) once suggested a rubric that I particularly like. Cuffs are sort of like the Times New Roman of menswear. They’re good for traditional, classic, and possibly staid looks. Plain hems, on the other hand, are like Helvetica, and are better suited to more modern, clean, or neutral styles. Whether you get cuffs or not just depends on the expression you want.  
To give some examples, I wear cuffs on any trousers that I might pair with a tailored jacket. So they go on grey flannels, linen pants, and dressy chinos. I also cuff jeans when I’m wearing more “classic” items, such as an oxford cloth button down, chunky cardigan, and white sneakers (as I’m wearing now).
With sleeker looking pieces, such as this black leather jacket I recently bought, I wear the same jeans, but unroll the hems. Same goes for any time I wear double black jeans, which I think of as being slicker looking than my indigo denim. 
In the end, just do what looks right to you. The only sartorial no-no is wearing cuffs on very formal trousers, such as those you’d wear with black tie. This is partly because cuffs are inherently a casual detail (they originated as mudguards) and because they interfere with the braid that typically runs up and down the legs. Aside from that, like Black Sheep said, the choice is yours.
(Photo via SpooPoker)

Turnup for What? 

If you ever find yourself waffling on whether or not you should cuff your trousers, Jesse has a great guide here that he wrote a few years ago. As he noted, cuffs are largely a matter of personal taste, although there are some general guidelines that can be good to follow. Pleated trousers, for example, almost cry out for cuffs, while flat fronts can go either way. And while you can more or less cuff anything, you’ll want to leave them off formal trousers (i.e. black tie pants) and perhaps your most casual (e.g. you can cuff your “dress chinos,” but you might want to leave them off the run-of-the-mill variety).

If you’re still left undecided, then here are two more useful guidelines.

  • Cuff everything. The reason is simple. You can always remove cuffs from trousers, but you can’t always put them in (depending on how your tailor has hemmed your pants). So unless you’re absolutely positive you want plain hems, err on the side of caution and request cuffs. You can get rid of them later if you decide you don’t like them.   
  • Think of typography. StyleForum member Parker (who’s day job is in graphic design) once suggested a rubric that I particularly like. Cuffs are sort of like the Times New Roman of menswear. They’re good for traditional, classic, and possibly staid looks. Plain hems, on the other hand, are like Helvetica, and are better suited to more modern, clean, or neutral styles. Whether you get cuffs or not just depends on the expression you want.  

To give some examples, I wear cuffs on any trousers that I might pair with a tailored jacket. So they go on grey flannels, linen pants, and dressy chinos. I also cuff jeans when I’m wearing more “classic” items, such as an oxford cloth button down, chunky cardigan, and white sneakers (as I’m wearing now).

With sleeker looking pieces, such as this black leather jacket I recently bought, I wear the same jeans, but unroll the hems. Same goes for any time I wear double black jeans, which I think of as being slicker looking than my indigo denim. 

In the end, just do what looks right to you. The only sartorial no-no is wearing cuffs on very formal trousers, such as those you’d wear with black tie. This is partly because cuffs are inherently a casual detail (they originated as mudguards) and because they interfere with the braid that typically runs up and down the legs. Aside from that, like Black Sheep said, the choice is yours.

(Photo via SpooPoker)