First time I visited Cutty Sark was back 1988 at 11yo and she was still lying in the dry dock with the keel resting on the blocks beneath her. There were some visible holes in the hull near the keel. Next time was in 2012, 3 week before the Olympics. This time she was lifted up from the dock and the the atrium had been build around her lower hull. Still a beautiful ship
"Cutty Sark" was heard often in old Scottish taverns. It was the custom for tavern patrons to have their own mugs to drink from. The personalized mugs were hung high on a wall. The barmaids wore a short top, a cutty sark, which just covered their breasts, barely. When a patron entered the tavern and asked for his mug a barmaid would have to reach up high, often on tiptoe. This extended reaching would cause the cutty sark to ride up, exposing her fair breasts, at which point the patrons would yell out in joy, "Cutty Sark!" What a wonderful old custom. ;-)
Robbie Burns lived in Alloway and regularly went drinking in Ayr returning home over the bridge across the river Doon. The Brig o’Doon. This was the semi auto-biographical inspiration for his poem Tam O’Shanter. Apart from the name of the tea clipper Cutty Sark, Brigadoon was chosen as the name of the magical village in the film of the same name.
I think the name was chosen from the poem to capture the chase won by the rider. All others shall see her transom even if they get a wisp of her spray (horses tail) in their faces.