Er zog das rote Jackett an.

Does this have a different meaning or connotation from “Jacke”? Or perhaps a different regional or contextual usage?

A Jackett is a Jacke but a Jacke only is a Jackett when it looks like the google image search results for Jackett. If you’re referring to a Jackett specifically you shouldn’t replace it with Jacke.

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Thanks! I get it, Google image search is fantastic for this purpose. Looks like “Jackett” is dressier. In English we occasionally call this a “jacket” but more commonly call it a “sportscoat” which is the silliest word because it’s exactly the opposite of the sort of jacket you would wear when playing sports. I’m sure it probably made sense many generations ago when the word was coined.

Coming back to think about this, although it’s certainly possible to have a “rote Jackett”, they seem pretty uncommon so it might be better to change the color to a more typical color like black, gray, or navy blue.