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Thomas Shoes owner David Thomas said his grandfather Arthur Thomas opened the family footwear shop Arthur Thomas Shoes Ltd, in King Edward St in 1921.
The business was continued by his father, also Arthur Thomas, in the mid-1960s.
In the early 1980s, his older brother Kevin Thomas joined the business.
David, of St Clair, joined the business in the mid-1980s and the two brothers ran it together until Kevin retired in 2014.
In the 98-year history, the business had been run from four shops in King Edward St.
The first shop was near the Mayfair Theatre, the rest were south of Hillside Rd.
The business would close at the end of the month and David would retire.
The time was right as bricks and mortar retail was getting tougher as more people shopped online.
He struggled to understand how people could buy a pair of shoes without wearing them first.
Over the years, the business had focused on selling different types of footwear.
As a boy, he had an after-school job in the shop inserting the laces in pairs of shoes.
The shop sold athletic footwear, such as Reebok, before big-box retailers came to town.
School shoes, such as Nomads, were another big seller.
"We used to stack them up about 20 boxes high and they'd all disappear.''
The pile of boxes of school shoes got smaller as pupils were allowed to wear a broader range of footwear.
As the retail landscape change, the business focused on a niche market, such as dress shoes, to survive.
The shop sold more women's shoes than men's shoes simply because on average, women owned many more shoes than men.
South Dunedin was once a retail centre and a destination for shoppers.
The retailers stayed open late on a Thursday and were some of the first in the city to open on a Saturday morning.
But things had changed and many retailers in South Dunedin had closed.
A change in bus routes had reduced the number of buses stopping in the area and decreased the amount of foot traffic for retailers.
He planned a relaxing retirement - a mix of bowls, golf, walking his cocker spaniel dog JayJay and playing with his seven grandchildren.
Operating the shop by himself was "full on'' and it would be with mixed emotions that he closed the doors for the final time.
"I'll miss the people but it'll be good to get away from it and do something else.''