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Jeans are universal IMO, but D&S I feel is a separate entity and feel then say blue label, same goes for Rugby at times. Don't get me wrong I do it and have done it. But unless you can make rock really well, I feel D&S and Rubgy give off different vibes that on a reg wouldn't gel well together. Keep in mind I'm referring to items that standout for there brand. Not say RRL jeans with a rugby sweater that don't count.
I think some of these sensibilities are generational too, but I'm with you, overall.
It's kind of hard to put a finger on exactly what I feel goes and what doesn't.
I also understand that full on traditional line-matching can be seen as paint by numbers and uncreative to some people... I don't care or agree, but I understand where they are coming from.