A General AviationAn aircraft is never required"Required" to be pressurized. The only reason to pressurize an aircraft is profit.
No one would ever buy an un-pressurized Phenom 100 or B777, but there is nothing stopping you from building one.
Pressurized aircraft are built because they can generate a profit for the manufacturer. Any aircraft can be made with pressurization but it comes with a price. If marketing determines it will sell, they will build it with pressurization.
You can look at pressurization as simply a comfort option. A comfort option that comes with a price.
There have been many cases of aircraft being built in both pressurized and un-pressurized versions.
The Cessna 402 and 414, Cessna 335 and 340, Cessna 210 and P210, Piper PA-31 Navajo and PA-31P Pressurized Navajo are all examples of the same aircraft built in both pressurized and un-pressurized versions.
In all these examples the un-pressurized aircraft can fly well above 20,000' but is generally operated at lower altitudes due to the inconvenience of using supplemental oxygen.