Hi Bernard, and Welcome to FireStryker!Most of our posters who are seamstresses are away at Pennsic, and posting to the board has been a little slow over the past week due to so many members absent as well. I can give you a inexpert answer, and hopefully someone more knowlegeable will chime in later.
It is my understanding that the houpeland, that is to say an overgown worn principly in conjuction with a doublet, is principly a 15th century item of dress, not appearing in England until either late in the reign of Richard II, or Early Henry VI, then remaining a staple of male dress (and feminine dress as well, although with a differing cut) until sometime during the Tudor era. Early houpelands differ radicaly in cut from ones post 1420 (the cut remaining similar from that point till they went out of use), with either large, belled sleeves with elaborate dagging, to bag sleeves baggy fom elbow to wrist, gathering together at the wrist.
I believe there were two radical changes of dress for the aristocracy during the era you are seeking to portray (50 years is a long span - a good lifetime for a man likely to be killed in accident, war, or in an epidemic - please note that people allowed to live out their lives without these outside factors could and did live into their 60's and 70's, occassionaly into their 80's, and the very rare centinarian - just like they did a generation or more back in the US, till medical care has expanded the average lifespan into the 70's today), so you will not get a consistant dress across the lifetime of a man born, say 1300, and perished c. 1350 - then again, how many people dress today as they did during the 1950's? You are lucky to have only two large changes across this span.
It is my understanding that through most of the High Middle Ages, a mans basic costume consisted of a tunic - the more voluminous the cut, and expensive the material the wealthier the man - and a pair of chausses and brais, with a variety of overgowns an surcoats (not neccessarily heraldic, and I am talking daily dress here), trimmed or lined with furs and the like, again dependant on wealth and station of the wearer. Sometime early in Edward III's reign, the costume of the aristocracy changed (but not the peasantry until near the end of his reign), to a more form fitting cote-hardi, cut to mid thigh, and getting shiorter as time went on, with chausses becoming longer and longer until they were split hose.
I think you will have to narrow down your time span to at least a decade, if you want accurate dress, or you will have to have diffferent sets of dress to represent different eras. The armour changes radicaly across that timespan as well, so there is more incenive to narrow down your time-frame.
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Bob R.