I am honestly surprised at the change in boat shoes recently. The styles are bizarre and the amount of companies that have a "boat shoe" have increased dramatically. Sperry's are now associated with middle school boys in khakis and the light tan ones have a bad reputation. I will always be loyal to the Sperry brand, and while they have strayed in the past, they are moving back towards their roots and the classic boat shoe.
In my opinion, there should only be a few styles and made as simply as possible. Minimal frills. These and these are such classics for both guys and girls, but these are just too fun. Red, white, and blue boat shoes? Swoon!
I am a firm believer that boat shoes should be strictly worn on a boat. Hence the name... BOAT shoes. However, I do think that there are certain instances where it is acceptable to wear them with the right outfit and the right setting. They are the perfect weekend shoe. The great thing about them is, that they fit better (and look better) the older they are. I still have my first pair (these - don't judge me, I guarantee your little brother has the same pair) from middle school and they fit like a glove! Definitely out of style, but perfectly worn in, so I wear them out on the lake or to clean the boat.
In the above photos, I wore a striped boatneck top, navy chino shorts, and Sperry Topsiders. This is something I typically throw on on a daily basis. The boatneck top pairs so well with the shoes. It was the perfect casual outfit for a Saturday morning enjoying coffee at a local coffee shop in downtown. I have linked other Sperry shoes that I'm loving right now!