Grrrrreat question, Thomas. This is typically something that comes up at the eleventh hour — in the tailor shop — because every time we alter a pair of pants for a guy, whether it's sport trousers or dress trousers or suit trousers, we ask if he'd like them cuffed or plain. And a key word there is LIKE... because a lot of it boils down to personal preference. Cuffs are never a dealbreaker. That said, here's how I approach it:
Okay, so the suit trouser is the easiest one, because with a dressier fabric (high-twist, sharkskin) we almost always like a cuff. It gives some gravity and heft and, in a way, it helps the fabric hang. This is in part because we prefer zero to very little break on our pants, so we don't want to give them the opportunity to hop and flop around. A cuff helps contain that. So generally YES to cuffing suit trousers.
Now there are exceptions... for me, cuffs become optional with a more casual fabric, whether it's part of a suit or not. For instance, I have seersucker pants with a plain hem, and same goes for my poplin suit. And I don't love cuffs when I'm wearing boots – like Chelseas or chukkas – mostly because they can easily get hung up on the top of the boot and spoil the vibe. Too much going on down there. And I like how plain-bottomed pants with boots give your silhouette a clean, minimal look. (Architects tend to favor uncuffed trousers, as do a lot of European guys, interestingly.) So anyway, I have non-cuffed flannel & corduroy pants for that exact reason. Another exception is tuxedos – I never cuff those. (I also happen to wear Chelsea boots with my tux fairly often, so it's a double strikeout there.)
So, getting back to your question – can you wear them with sport trousers? Absolutely. And if you're into the way they look on dress trousers, my guess is you're going to dig the lift they'll give to your sport trousers, too. I'd say about half my sport trousers have cuffs... and for me it's a gametime decision based on the fabric and what else I'm wearing. The more casual the fabric and shoes – like cotton or sneakers – the higher probability I'm going for plain bottoms. And the dressier the fabric and shoes, I'm probably going cuffs. It's a feeling more than an exact science... so be confident & fly your own kite.
Lastly in terms of the cuff height... I think the most ideal proportion for pretty much every guy – myself included – is 1.75 inches. Sounds like you're a fan of the 2-inch cuff, which is cool, but don't be afraid to cut it down just a smidge. It'll make the cuff a little less of the star of the show, which allows you to experiment with different fabrics, colors, patterns, or other fun things.
At the end of the day, almost every trouser works with a cuff... but there are some times when plain bottoms are gonna look the part, too. Long story short, it's hard to go wrong. Hope this helps!
P.S. If you want a little more of a formula, we put together a flowchart that might help you decide
