It seems a bit try-hard / cliched to me tbh. It's a look that was around a lot in the late 90s / early 2000's. Often seen teamed with a pinstriped trilby, distressed jeans and pointy shoes.
I'm sure it can be pulled off, but I think that they should only be worn as part of a suit really. It's a combination that is often seen on waiters, bartenders and so on, so it'd be important to make it obvious that you weren't at work. I just don't see how it can be done.
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