I consider myself to be an expert on shoes, but when a friend casually mentioned her quest for a pair of winklepickers, I was flummoxed, to say the least. How, as a fashion editor, did I not know of this particular style of shoes?
Winklepicker boots were made popular in Britain in the early Sixties. They are known for their pointy toe, which is an ironic reference to the particularly English custom of eating periwinkle snails, wherein the, erm, animal inside the shell has to be extracted. Culinary delights aside, the shoes first gained traction among the Mods in the 1960s, and is recently experiencing a renaissance, having been spotted on bands like Kings Of Leon and The Kills.
The boots are pretty extreme: pointy toes and metal buckles make them perfect for hitting the stage at CBGB (or its modern-day equivalent). We, on the other hand, are looking at the winklepicker's more subtle cousin, the Beatle boot. Named after the iconic band for which they were designed, the toe is still curved, but it's much softer, and the conical heel is just low enough to make for comfortable shoes that you can actually, you know, walk in. These boots are perfect with jeans (cuff those boyfriend jeans to show off your ankles), or with dresses and tights come winter. Bonus: There's no need to fear tripping over boots that could double as skis.
Here, nine pairs of pointy-toe boots for fall.