You can get this pin by getting 5 hearts in the Trial of Style. The more often you get 5 hearts, the higher the level of the pin will rise.
This is the amount you need:
|Level||Receive 5 hearts|
After reaching the 5th level, you can level this pin again with the same number. After that, the color no longer changes, but a number appears on the pin. This shows other users how many times you have reached the last level.