The Areni-1 shoe
The oldest leather shoe is 5,500 years old — size 37

In 2008 Armenia's Areni-1 cave produced a shoe cut from a single piece of hide, with laces and stuffed with grass: the oldest known leather footwear. It is roughly a European size 37, and the same cave later revealed the world's oldest known winery.
Wikipedia (Russian) · Wikipedia (English) · 35th century BC
Did you know
The world's oldest leather shoe is 5,500 years old — and roughly a European size 37. Found in Armenia's Areni-1 cave, it was cut from a single piece of hide, still had its laces and was stuffed with grass. Share →
The oldest known winery is some 1,500 years older than the Great Pyramid. It was found in Armenia's Areni-1 cave, home of the oldest shoe, where wine was made around 4100–4000 BC. Share →
Meanwhile around the world (±25 years)
Europe
- c. 3500 BC The invention of the wheel — same year