The first thing you should do is to check which version CircuitPython is installed.
You simply don't know how long your board was stored at the factory and/or shop.
Connect the Itsy to your computer USB port and log in via the serial port. With Putty in my case.
Stop any running program with CRTL-C, and hit CTRL-C untill you see the Python command prompt (>>>).
Now you see which version CircuitPython is used. This is the output of my, unmodified, ItsyBitsy:
Adafruit CircuitPython 3.1.1 on 2018-11-02; Adafruit ItsyBitsy M4 Express with samd51g19
At the time of writing (8 sep 2019), the latest CircuitPython version is 4.1.0.
Which means I will definitely update the Itsy, because it is a major version behind.
Plug your Itsy into your computer using an USB DATA cable.
Double-click the small Reset button on your board, and you will see the Dotstar RGB LED turn green.
If it turns red, check the USB cable, try another USB port, etc.
Adafruit CircuitPython 4.1.0 on 2019-08-02; Adafruit ItsyBitsy M4 Express with samd51g19
The latest (at time of writing) firmware is installed on the ItsyBitsy M4
Unzip the file, open the resulting folder and find the lib folder. Open the lib folder and find the library files you need to load. Create a lib folder on your CIRCUITPY drive (if you don't have one already). Copy the library files, with .mpy extension, to the lib folder on your CIRCUITPY drive.
The latest CircuitPython Libray Bundle Release.