Is pin rolling denim really acceptable? How is the look best achieved? How do you pin roll?
That’s a great question, and the answer is a resounding and authoritative “It Depends.” Pin rolling is an effective way to deal with unwanted volume below the knees of your pants (including jeans), and I employ it regularly on chinos (a dissertation on that highly scientific procedure can be found here). If you don’t like the cut of your jeans, particularly dark-rinse denim, my first suggestion would be to see a tailor. A good one can make your jeans slimmer the whole way through or just peg them a bit, and he/she can most certainly shorten them.
The best case to be made for pin rolling denim, in my opinion, has to be vintage jeans. These are broken in (either by you or some other person), and taking them to the tailor might screw with the wear lines, which is why you bought them (and in some cases wore them for years on end) in the first place. Styles change, and where it might have been good for them to be long and wide once, this is no longer the case. Here is where pin rolling will feel the most organic.
Let’s face it, pin rolling is a styling technique that can look contrived, and the best way to counteract that is to use it when it’s actually necessary, like in the case of vintage denim. If none of the above options seems like the one for you, there’s always the most extreme tack you can take: Buy new jeans.
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