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Today it's kinda cool (upper 50's) with chance of showers, but the rain is supposedly coming to an end.
I chose to wear tan leather goods (double-monks, belt, and watch strap), brown socks, light tan chinos, a violet no-iron dress shirt, and navy blazer. Pocket square not a necessity today, but I grabbed a silk one: magenta base, with an oversize paisley pattern of a wide array of blues with a little white. Had a heck of a time deciding which flat cap to wear out in the drizzle:
Ivory cotton,
or herringbone Harris tweed in a dark blue colorway.
(Tried to get a picture of the options, but it turned into a movie of the ground and my feet... Darn cell phone. Can try again later if anyone needs the visual reference.)

I went with the blue, and did get a compliment on today's look. If it's really raining, I'll grab what's nearest / most likely to keep me dry - practicality over fashion.
But when I have the option (like today) is it generally more appropriate to coordinate headwear with outerwear / jacket? Or to grab something to complement the pants?
 

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I prefer not to think of the ensemble as pants vs jacket/outerwear. Start with whichever item you want but then coordinate color, pattern and texture (if you're good enough, I never get much past color) around that. And really, it doesn't matter where you start. I see no problem with starting with a cap (of which I have a plethora) or even shoes. But start somewhere and stick with it.
 

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I like the hat to coordinate with the jacket or outerwear because of their proximity.

With that said, I'm sure it's fine to coordinate your hat with your pants, because I'm equally sure that your pants are coordinated with your jacket - that is, the whole ensemble is coordinated and all works well together.
 
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