Sperrys are the "wanna be" version of top siders. They're only like 50 bucks and are extremely uncomfortable. Those who wear them refuse to acknowledge the pain because they are so desperate to convey the preppy boater look. Those who actually wear top siders for their intended purpose know the best brands and like to keep it that way because they are the genuine people who the top sider supporters aspire to be.
Hahahahah, you wear sperrys
by Anon Anforth griffen December 07, 2007
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A type of boat shoe worn by frat boys and classy gals, that is worn without socks.
"I'm really digging the Sperry's." - Carly

"Thanks. All my friends wanted to buy a kind of shoe that can be worn without socks, and Sperry's were the obvious choice." - Ralph
by GoGetterCFerg July 17, 2020
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