A Drinking Town With a Sailing Problem

As most of you know, I am a sucker for high heels. It is rare to see me in a pair of flats and during the summer I almost exclusively wear my espadrille wedges. But I also come from Annapolis Maryland, home of the Naval Academy and Way Too Many Drunk Sailors.

Boat shoes are kind of our thing. So, when I saw these in the J. Crew catalogue (that is addressed to me, yet gets sent to my parents house so when I visit them I always have a nice pile of catalogues) I got far too excited. I do not own Sperry Topsiders, but I appreciate the aesthetic in a most disturbing way. My love for them is very similar to the comfort I feel when I walk by a woman wearing Lilly Pullitzer. One of my best friends from grade school named her bischon Lilly and painted her room pink and green. This is the life of an Annapolitan prep-school girl.

Well, moving on, these are shiny gold Sperry’s and no one should ever wear them sailing (yet I am of the belief that sailing is most enjoyed naked and with a cold beer, because my parents went to St. John’s college) but they are absolutely amazing. $98 from J. Crew