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Outside Charger Waterproof?

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I cannot speak for the 14-50 but I have a Tesla Wall Connector installed outdoors, as do many other owners and destination charging locations. Some people put roofs over them to help keep rain/snow off them, and that does seem like a good idea, but I have not done that. (It is, however, a good idea to try to keep snow out of the inside of the cable connector and the charge port, because it can interfere with proper seating of the connector in the charge port.)
My car often charges just fine when it is snowing or raining.
Having said that, my WC failed after about 2 years and was replaced by Tesla. I do not know if moisture was a factor, but the electricians who replaced it did not suggest covering the new one.
 
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It is rated NEMA 3R which means:

"Weather-resistant. Protects against falling dirt and windblown dust, against weather hazards such as rain, sleet and snow, and is undamaged by the formation of ice. Used outdoors on ship docks, in construction work, and in tunnels and subways."

Except that the R means windblown dust protection is not guaranteed.

Now if you look up Tesla charging opportunities in Australia you will see that outside oF metropolitan areas most are HPWC destination chargers (HPWC) mounted outdoors. I guarantee that any HPWC mounted outdoors in the outback of Australia is subject to blowing dust!

Covers are gasketed and the wires must enter through an appropriate gland.

A 14-50R mounted in a NEMA 3R enclosure will enjoy the same level of protection as an HPWC.
 
As mentioned, the wall connector is made and rated to be an outdoors device in the weather. All of the thousands of destination charging points at hotels are outdoor wall connectors. A 14-50 with the mobile cord can be used, but of course isn't as protected where it plugs into the outlet, so for people's permanent daily installations, I would recommend a wall connector if it has to be outdoors.