Top-Siders

I remember breaking up with one guy because he wore shorts with Sperry Top-Siders far too often.

The Lo-Down Lo Bosworth 2011

For a northeasterner who knows his way around a boat, slipping sun-tanned feet straight into Sperry Top-Siders, canvas sneakers or even penny loafers comes as naturally as hoisting a jib.

Grin and Bare It Darrell Hartman 2011

I remember breaking up with one guy because he wore shorts with Sperry Top-Siders far too often.

The Lo-Down Lo Bosworth 2011

This is why we wear Top-Siders, so buy Top-Siders!

Christian Chensvold: Preppy Evangelist: The Lisa Birnbach Interview Christian Chensvold 2010

This is why we wear Top-Siders, so buy Top-Siders!

Christian Chensvold: Preppy Evangelist: The Lisa Birnbach Interview 2010

Despite lacking all the skills that would provide us with the lifestyle we strongly felt we deserved, we knew that one day we would wear our own Top-Siders, actually worn down by us from use on our eighty-foot pleasure craft.

i know i am, but what are you? SAMANTHA BEE 2010

Despite lacking all the skills that would provide us with the lifestyle we strongly felt we deserved, we knew that one day we would wear our own Top-Siders, actually worn down by us from use on our eighty-foot pleasure craft.

i know i am, but what are you? SAMANTHA BEE 2010

Jamie was supposed to be an excellent sailor, and for the audition, Tally had bought an outfit that fit the profile: white jeans, a blue-and-white-striped boatneck top, and Sperry Top-Siders.

Starlit Lisa Rinna 2010

Or, for a sillier affair, slip on your Sperry Top-Siders and try the College Humor and Guest of a Guest Yacht Rock party at the Hotel on Rivington Penthouse, 107 Rivington Street, starting at 8 p.m.

The Observer's Guide to Geekery at Internet Week New York 2009

Or, for a sillier affair, slip on your Sperry Top-Siders and try the College Humor and Guest of a Guest Yacht Rock party at the Hotel on Rivington Penthouse, 107 Rivington Street, starting at 8 p.m.

The Observer's Guide to Geekery at Internet Week New York 2009