I concur with
@jmaddr; when charging outdoors, it's better to use a hard-wired EVSE with appropriate weatherproofing. There are two weatherproofing ratings that I often see on EVSEs: NEMA 3R and NEMA 4, with 4 being the better one. (See
this page, among others, for detailed descriptions of what these ratings mean. Note that these are unrelated to the NEMA numbering for outlet types, like 14-50.) Tesla's
Wall Connector manual explicitly states that the device has a 3R rating. Some others, like most or all Clipper Creek and EnelX (JuiceBox) devices, have NEMA 4 ratings; however, I don't know how the fact that you'd have to use Tesla's J1772-to-Tesla adapter with those would impact weather resistance on the plug end. Some EVSEs have no weather-resistance rating; they're intended to be used only inside. Thus, if you're considering a third-party device, be sure to research this detail. Also, most manufacturers seem to recommend hard-wiring EVSEs that are to be mounted outdoors, rather than buying a model with a plug and installing a 240v outlet outside.
FWIW, I park outside -- I have a driveway but no garage. I bought a Clipper Creek HCS-40 in 2016, for use with a Chevy Volt. When I bought my Model 3 in 2019, I decided to keep using the Clipper Creek EVSE, just with an adapter semi-permanently attached to it. This has worked fine for me outside in Rhode Island, with both the Volt and the Model 3. That said, I do prefer to unplug the car before major rain or snow, just to be extra-cautious. (It also helps to not have to shovel snow from around the charge cord.) That said, if I were buying a new EVSE for use with my Model 3, I'd probably get a Tesla Wall Connector. Tesla's prices are competitive, and not having to use an adapter would be a small advantage.