Probably in former times, Kings, Emperors, and Princes wore rings on several fingers of both hands as well as stars, crosses and medals of all kinds on their breasts and that habit is not entirely lacking in modern days. But a Prince Mason or Masonic Emperor, Sovereign, Knight or King could not wear all of this, even within a lodge, council or chapter. Masonic rings are made for Master Masons, Past Masters 14th Degree, 33rd Degree, Past High Priests or Order of the Purple Cross in addition to the double eagle emblem of the Scottish Rite. If the Mason is martially sentimental he may wish to wear a wedding ring. So, there must be more or less a permanent choice, unless a Masons wishes to change his rings as he changes his apparel. The very abundance of rings may even retard the use of any by becoming so common that little distinction arises from wearing one. A ring is worn undoubtedly to be seen by others and the choices may be made between one which will appeal to a small but select group of Masons, such as 33rd Degree or Order of the Purple Cross, or one that will be appreciated by a much larger but still limited group such as Past Masters. The most widely recognized would be the simple Square and Compass. but those have become so numerous as to excite little comment unless of very extraordinary design.

Probably nothing can raise a more heated or less fruitful argument than the question of whether the square and compass ring should be worn with the points of the compass pointing away from the wearer and hence making the symbol right side up when the arm hangs down and as another person sees the ring, or whether it should be worn as to be right side up to the wearer. Grand Lodges take no cognizance in this matter and in fact, the symbols of the

Square and Compass have become symbols by usage, not by express adoption of Grand Lodges. The common sense solution to the problem is, therefore, that since the ring is worn for others to see and to inform them that the wearer is a Mason or Past Master, it should be worn upright to the observer. It also seems in appropriate that when the arm hangs naturally the emblem would be upside down.

(Source Coils Masonic Encyclopedia)