Thank you for writing to the Dell Community Forum.
The Latitude 5285 system has a USB 3.0 Port and an external DVD drive can be connected. It has a USB Type-C (Refer to this link http://dell.to/2vsCU9w) and you would require a Dell adapter USB-C to HDMI/VGA/Ethernet/USB 3.0 to connect an external display (Refer to this link http://dell.to/28RIlmw).
Kindly get back if there are any further queries.
For me to better assist in troubleshooting, please click my DELL-username and send me a Private Message with the Dell Service Tag number and your email address.