These days, people want to know "why are you so dressed up?" when they see an outfit like this, but to my mind, this outfit is nothing more than a gentleman's casual, just this side of rakish.
To wit, the excessively frayed shirt collar, tie worn intentionally loose,
and rolled khakis, sockless (of course) with navy blue Sperry sneakers.
But the tie is the thing here. Real bleeding Indian madras (which seems to be all over the menswear bloggy charts lately(see here, and here)...call me a sheep)). A vintage, square-ended relic from Rooster. I invite the older of my readers to share reminiscences of Rooster clothing.
From a place called "Town & Tweed Shop" in Lynn, Massachusetts. Sounds like my kind of store, although its hard to believe Lynn ever was home to such a place. If you're local, you know what I mean, if not, take my word for it. There's a silly poem around that starts "Lynn, Lynn, city of sin..." You get the idea.
The things you can find for a buck.