It took me a while to buy and feel comfortable in a pair of boaters and I started with a few different pairs of Sperry, one pair made from two originals with eyes 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.