I love a great pair of cuffed boyfriend jeans. So comfortable yet stylish for days when you want a little leg room. I try to not to overthink the "cuffing" part. I purposely leave one side a little different than the other so it doesn't look like I'm trying too hard. Maybe fold one twice and the other once. Leave one side slightly higher than the other. After all, the whole point of boyfriend jeans is to look off duty and relaxed like you just threw them on without a care in the world!
I style mine usually 1 of 3 ways. With cute sneakers for running around town, with a classic pump for going out, or with a great wrap up pointy flat for those times in between. I also usually wear a bright lip to kind of balance that boyfriend, slouchy look.