Sir Waterly is dressed in armour typical of the late 14C (and early 15C). He wears a coat-of-plates rather than a breastplate, and has full plate arms, legs and gauntlets. He is armed with sword, dagger and heater shield, which was still in use by knights in this period, drifting out of use later in the 15C. In the smaller picture he is holding his pole-arm of choice, a glave.
You will note Sir Waterleys liking of black in his armour and costume, this is is due to the fact he likes to take on the role of the "black knight" in our displays, and is often found to be fighting in un-chivalrous ways! One of his favourite sayings is "the best time to kick a man is when he's down"
Armoured pictures
Civilian Clothing