A weather resistant connector system includes a connector housing having a first open end, a second open end and a first interior space defined within. A boot has a first open end, a second open end and a second interior space defined within. The second open end of the boot is attached to the first open end of the connector housing. At least one engagement element is formed on the connector housing for engaging with a complimentary structure proximate a port. In one aspect, the boot is flexible and bi-stable, having a first at-rest shape and a second at-rest shape, with the first at-rest shape having the first open end of the connector housing located closer to the first open end of the boot, as compared to the second at-rest shape. In another aspect, the boot is flexible and has a first at-rest shape and the boot can be moved to a second, unstable shape, when a manual force is applied thereto. In a third aspect, a cable enters the first open end of the boot and the boot may be slid toward and away from the port along the cable.