You should always check the "update paths" to verify compatibility: https://interopmatrix.vmware.com/Upgrade?productId=2
You have to do these steps: 5.5 -> 6.0u3 -> 6.5u3
P.S: End of General Support for vSphere 5.5 https://kb.vmware.com/s/article/51491
Do you need to stay on vCenter for windows? It is deprecated since vSphere 7. And vSphere 6.5 and 6.7 is already end-of-support since 15.10.2022.
If you need to stay on vCenter for windows, I recommend doing small steps. So upgrade from vCenter 5.5 to 6.0 and then to 6.5. From there you should migrate the vCenter for windows into an appliance of vSphere 7.