These are the earliest coats of arms for knights in Annandale that I have been able to find. The earliest is that of Annan, also styled Annand. Times were turbulent in the years 1066-1250 AD, and life expectancy could be short. So it was with the unfortunate Annan. His young wife inherited both his lands and his coat of arms. When she remarried to Robert Bruce, the first in a long line of this name, he did well for himself, gaining her lands and adopting her coat of arms which he personalized. This Robert was based in Northumbria and preferred to remain there. When King David I of Scotland asserted his right to Northumbria and Cumberland, Robert did what many did in those days. He divided his estate, giving Annandale to his son Robert and remaining on his estate in York. This way no matter which side won his family still could make a case for holding onto their lands in both England and Scotland with their respective kings. It worked in his favor. England gained sway over Northumbria and Cumberland, and Scotland retained Annandale. The Bruces won.

It was very common in this time period for sons to move out of the family castle or home, go to another place and take a different surname, one that had something to do with the local area to which they had moved. This explains the different surnames associated with the Bruce family and their Annandale style coat of arms.