What are winklepickers?
Correct answer: A shoe with a long pointed toe

AppleA815
Here in NY, we call them roach killers; you can squash them in a corner

Taramaiden
Famous question to a Mod wearing winklepickers, from a London Bobby in the 60's: 'Do your toes go all the way to the tip of your shoes?'
Mod's reply: 'Does your head go all the way up to the top of your helmet?'
Quite!

little b
i dont like a shoe 👟 with a long pointed toe

MicheDu
AppleA815, we called them Beatle boots

Mars V
Longest answer…👍

Erika
AppleA815, In South Africa as well

saylu
In Spain this sort of boots are called 'chúpame la punta' or just 'chupamelas'

K9Queen
Knew this thanks to the game Animal Crossing

joe donut
cockroach killers

James
We used to call them snake kickers 😊

NoxiousWitch35602
Credo ergo sum., did the same thing