The word in question in the MT is מעונן, m'onen. The question is, if Gesenius translates this as someone who "clouds", covers, or uses dark arts, then why does the KJV translate as "observer of times"? There appears to be no connection.
Furthermore, what is an "observer of times"?
The answer, as is often the case in things KJV, is that the KJV is translating according the mainstream Jewish tradition as represented by RASHI. RASHI interprets the word מעונן in this verse not as a form of ענן, anan, cloud, but as a form of ענה, onah, meaning a period of time or season, as in "the football season". So RASHI's interpretation is that a m'onen, מעונן, is someone who "seasons", that is, someone who determines via astrology or similar arts that particular times are ripe for for doing particular actions or making particular decisions.
Now the question is why does RASHI read מעונן as someone who "seasons", which sound a little stretched, instead of the more likely reading as someone who "clouds", that is, someone who uses smoke screens or ruses to do some unspecified thing. The two answers to this question are that a) that the "clouds" reading doesn't tell us the specific nature of the activity that is prohibited, which is unsatisfying to someone like RASHI who reads the text as a manual to live by, and b) the "clouds" reading does not provide a clear enough distinction from the last word in the verse, מכשף, mechashef, a practitioner of witchcraft, so it sounds redundant.
For reference, RASHI's actual comment on this word in this verse is a quotation from a midrashic commentary:
רבי עקיבה אומר אלו נותני עונות, שאומרים עונה פלונית יפה להתחיל. וחכמים אומרים אלו אוחזי העיניים
Rabbi Akiva says, these are [people] who give seasons, who say, "this time is a good time to start [something]". And the sages say, "these [people] are holders of the eyes (deceivers)".
As an aside note, when RASHI uses a midrashic commentary, it usually means that he doesn't have a more straightforward linguistic answer, or that the linguistic answer is somehow unsatisfactory.