Might not be really medieval, but: Thoughts on Romanness in the 6th century? I mean, we have the Penmachno inscription with a citizen of Gwynedd (venedotis civis) and ive seen argued that cymry/cambri as "fellow countrymen" is a related to civis=citizen. The Saxons et al I'm happy to believe that came as soldiers seeking payment in land when the empire could no longer pay in cash. How much of the daily life was recognisably (late) Roman to someone, let's say, who came from the continent?
I think it's generally considered that Wales and parts of England close to the Welsh Marches would be considered the last vestiges of Rome.
I mean, Chester was still manned by the Roman legion until the retreat from Britain in the 5th century, but the Roman-British population would have still been there, as well as the veterans from the legions who'd retired to lands near it.
So I think in general, life would have been Roman enough for a casual observer to see that Rome had Romanized Britain enough, but by the 6th century, it would have begun shifting away to the beginning of something we'd call Anglo-Saxon-esque. Largely, there would have been a lot of Roman style arms and armour still being used, as well as general cut of clothing and such.
It would have existed but in a transitional stage.
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