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The Order of St. Anna (or "Order of Saint Ann"; Russian: Орден святой Анны) was a Holstein and then Russian order of chivalry established by Karl Friedrich, Duke of Holstein-Gottorp on 14 February 1735, in honour of his wife Anna Petrovna, daughter of Peter the Great of Russia. The motto of the Order was "Amantibus Justitiam, Pietatem, Fidem" ("To those who love justice, piety, and fidelity"). Its festival day was 3 February.

Initially, the order had but one class and was named the "Order of Anna". The statutes of the Order promulgated in 1735 established as the principal insigne a gilt and red-enameled cross, with an image of Saint Ann imposed upon the center of the cross; the reverse bore the initials "A.I.P.F." (for "Anna Imperatoris Petri Filia": "Anna, Emperor Peter's daughter" in Latin). The same letters also abbreviate the Latin motto (as the letter "J" did not exist in Latin, "Iustitiam" was the original spelling of the word now rendered "Justitiam").

In 1742, Karl Peter Ulrich, Duke Karl Friedrich's son, was declared the Russian heir apparent. After arriving in Russia, he presented the Order to several courtiers. On 15 April 1797, his own son, Emperor Paul I of Russia, established the Order as part of the Imperial Russian system of honours and divided it into three classes, renaming it the "Order of Saint Anna". Emperor Alexander I added a fourth class in 1815.

Recipients of the Order of St. Andrew (including princes of the imperial blood, who received it at baptism) simultaneously received the first class of the Order of Saint Anna. The emperor himself was the hereditary chief of the Order.

The title of Chekhov's well-known story Anna on the Neck refers both to the Order and to the heroine.

Order of St. Anna, 1st class

Order of St. Anna, 2nd class (The example shown is "with swords", for bravery in battle, and crown)

Order of St. Anna, 3rd class

Order of St. Anna, 4th class (The insigne with imperial eagle would have been awarded to a non-Christian, for whom a Christian cross was deemed inappropriate)

• 1st class: Cross worn at the bow of a broad ribbon (ten centimeters wide, worn over the left shoulder), on the right hip; star of the Order (about 95 millimeters in diameter) worn on the right breast;
• 2nd class: Cross worn on a neck ribbon 45 millimeters wide;
• 3rd class: Cross worn on the left ribbon, suspended from a ribbon 28 millimeters wide;
• 4th class: Cross borne on the pommel of an edged weapon, together with a silver-tasselled sword-knot of the ribbon of the Order.

A recipient of higher classes of the Order would not wear insignia of lower classes, unless he had also been awarded the fourth class (the insigne of which was borne on the hilt of a sword or other edged weapon).

Alan W. Hazelton, The Russian Imperial Orders; New York: The American Numismatic Society, 1932 (Numismatic Notes and Monograms, No. 51).

• (Russian) Order of St. Anna
• (Russian) History of the order of St. Anna