I just got into handbags two months ago. Among my purchases, I bought one Coach and one LV. While both are handsome and wellmade, the LV speedy is my favorite. The Coach I bought was the from the Pebbles leather collection and it's a pretty mahogany. I HATE HATE HATE Coach's fabric monogram bags; they look so tacky, IMO (sorry if that offends anyone).
About which is more timeless, I feel that the Coach leather bags have the possibility of being timeless bags, but those sig ones are waaay trendy!