What sorts of clothing would have been worn by a well dressed man in the mid 1400s?
That depends on the geographical region to which this man lived. Where would that be? If you are referring to the voyager, Wikipedia states John (his English name) was not born until 1450, so I would guess the attire you are looking for is closer to the 1470-1500. It appears that burgundy, and later the color black, were popular colors worn by men during this period. A houppelande or houpelande is an outer garment, with a long, full body and flaring sleeves, that was worn by both men and women in Europe in the late Medieval period. The Houppelande, in Italy called the cioppa, is the characteristic overgarment of the wealthy in the first half of the 15th century. It was essentially a gown with fullness falling from the shoulders in organ pleats and very full sleeves often reaching to the floor with, at the start of the century, a high collar. It was initially often worn belted, but later mostly hanging straight. The length of the garment shortened from around the ankle to above the knee
