Re:So, ywimpled would mean wearing a wimple or being a nun.

i think, in chaucer time, that wouldn't be entirely true... nuns 'habits' were fashioned from widows weeds, and reflect the proper garb for a woman in mourning.(at the time the order was created.. so old habits are almost a history of fashion!)

if the royal court were in mourning (as it was for many years during queen victoria's times) everyone in court would wear some sort of mourning garb--

widows weeds(at chaucers time) would have include wimples. so to 'be wimpled' could mean a nun, or just a woman in mourning attire, either for a husband, or someone else-(parent, etc.)

it was not uncommon for widows to live in convents, (even if they did not take the vows of a nun) they would have been entitled to a dowerage (1/3 the income from their late husbands estate), but not entitled to live in the household--(they could if the heir let them.. but lets face it, who want to live with your mother or stepmother?--especially if the law support the idea of you throwing her out of the house?)

so widows often lived with (and dressed as) nuns. but would still have some income, and if they had enough, they could travel.

if there was a death in the royal family (and Edward had half a dozen children who died) the whole of the court would go into mourning.. and the ornate wimples and headdresses would have been a common dress.

if a man died with no sons, his daughter(s) would inherit the estate, (as did Blanche of Lancaster) she would have been in mourning, but wealthy, and entitled to live on the family manor (as she did, after marrying john of gaunt.)
(one of the newer orders,(RC) the sisters of charity, was found at in ny , just after the civil war, and the 'habit' of the order is (was) the same sort of outfit you'd see on a widow of the time (they wear bonnets, with large visors, and ornate bows tied under their chins, not veils, and a pleated cape over a shirt waist dress, as a habit)