It took me a while to buy and feel comfortable in a pair of boat shoes, so I started with a few different pairs of Sperrys, a pair of original twos -Eye models and another made from recycled plastic. When I tried the Gold Cup, it was like a Rolls-Royce Topsider. Very comfortable with a classic look that will last with good care and well worth the extra money. I would suggest wearing them with panels not visible to protect the leather insoles so they last longer.