Why items are priced at .99c or at odd decimal digits?

Two main reasons:
* Loss prevention: the .99 pricepoint was a very early form of loss prevention,nventory control, and accounting.
There was a fear that when pricing something at 1.00 would result in the cashier pocketing the money, whereas a .99 item would mean that he would have to open the register and give a penny in change. Not a lot of registers printed receipts back then.

You can also check the amount of items based on the day's take, using simple math. Example, if the total till take ended in .56 it means that 44 (or 144) items were sold, regardless of the amount of customers.

That price point stuck, but it was really helpful to run a business efficiently. (Quora)

Psychological pricing or price ending is a marketing practice based on the theory that certain prices have a psychological impact. The retail prices are often expressed as "odd prices": a little less than a round number, e.g. $19.99 or £2.98. The theory is this drives demand greater than would be expected if consumers were perfectly rational. Psychological pricing is one cause of price points. (WIKI)
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