These days it seems like only the few, fawned over brands bother with building goods handsome and built to last. But once upon a time that wasn’t the case, and even at not-so-chic Sears you’d find scrumptious sweaters made by Ohio Knitting Mills and wingtips as deadly and dapper as the four in my collection.
The first pair wound up in my possession randomly, as part of a costume for a film, and a size and a half too large for me. But the second set were selected because they were the most striking of all the brown wingtips in my size at a local vintage shop.
The rest were sought out specifically on e-bay, and although the era and interior Sears emblem varies a bit from style to style, each pair is rock-solid outside and pillow soft inside. With vintage wingtips, if the leather is too pebbly or too dull the shoe reads as too dusty, dated and drab – but the Sears shoes are grained and glossed just perfectly so.
And, apropos for a Sears shoe, even a rare vintage one, I’ve never paid more than $19.99 for a pair. If Alden or Trickers wingtips elude you economically, go see the softer side of Sears.










































