A friend of mine won a trip to Montego Bay some years back. This was during the time frame when it was fashionable to wear timberland boots. This doofus came back with pictures of him on the beach --in timberland boots--. When I asked him what he was thinking g, he told me he was keeping it real... I had not thought about him or that incident in years, but it was the first image in my mind from your post. Boots and the beach (or cliffs) are not a good look