The idea behind obfsproxy is that you don't want it looking like port 443 on the wire. You can infact mask the traffic using the domain fronting technique providing you setup obfsproxy correctly. I haven't tried it myself, but I have analyzed Tunnelbear's 'ghostbear' feature with wireshark and the traffic looks fairly innocuous which is what we're aiming for.

https://community.openvpn.net/openvpn/wiki/TrafficObfuscatio...