I have been and will always be known as a man who opts for comfort and practicality over fashion (that'll be the prep in me then). I don't do skinny jeans or fully buttoned shirts for this very reason. I like to be able to sit down without my clothes tearing and I hope to be able to have children one day so I am concious of protecting what needs to be protected in order to make that happen. Skinny jeans seem counter-productive in that respect.
Comfort also applies to my tired feet. For a writer I seem to be on my feet an awful lot. Thus the first item on my Must-Have list is an old friend of mine. The Boat Shoe. These shoes seem to be very much in fashion at the moment, however preps like myself have been wearing them since way back when. In fact, they were as good as uniform at the school I attended. These shoes seem to last forever and, even when they started to fall apart (with the sole flapping away from the upper), are always acceptable footwear. My personal favorites are a brown pair of dubes with white soles and a light blue pair of Sperrys. I have never tied laces on mine.
Here are some of the choiciest options:
Sperry Top-Siders
Needing no introduction, Sperry Top-Siders are the boat shoe of choice for the American preppy male. Available in a wide range of colours, fabrics and styles these are the Must-Have casual shoe. Check out the range launched in conjunction with designer Band of Outsiders... trés chic!

Sperry also have a range of slip-on shoes and other boating shoes. Collect them all!
Sebago Docksides
An alternative to the Sperry Top-Sider. Both have their die-hard fans. Sebago has a solid reputation for durability and comfort. Sebago also produce a wide range of boat shoes but the Dockside is undoubtedly their best.
Dubarry of Ireland Deck Shoes
The 'Dube' is the first choice for British and Irish preps (and was the shoe of choice during my school years). Dubarry have been making fine boating shoes for a long time. Best worn tatty with the laces curled and NEVER tied.
Others
Musto Performance also do a great range of boat shoes that are worthy of consideration.
Eastland Knot
This is how boat shoes should be fastened.
Musto Performance also do a great range of boat shoes that are worthy of consideration.
Eastland Knot
This is how boat shoes should be fastened.