From BiblePortal Wikipedia

Vine's Expository Dictionary of OT Words [1]

'Esher ( אֶשֶׁר , Strong'S #835), “blessed; happy.” All but 4 of the 44 biblical occurrences of this noun are in poetical passages, with 26 occurrences in the Psalms and 8 in Proverbs.Basically, this word connotes the state of “prosperity” or “happiness” that comes when a superior bestows his favor (blessing) on one. In most passages, the one bestowing favor is God Himself: “Happy art thou, O Israel: who is like unto thee, O people saved by the Lord” (Deut. 33:29). The state that the blessed one enjoys does not always appear to be “happy”: “Behold, blessed [KJV, “happy”] is the man whom God correcteth: therefore despise not thou the chastening of the Almighty: for he maketh sore, and bindeth up …” (Job 5:17-18). Eliphaz was not describing Job’s condition as a happy one; it was “blessed,” however, inasmuch as God was concerned about him. Because it was a blessed state and the outcome would be good, Job was expected to laugh at his adversity (Job 5:22).

God is not always the one who makes one “blessed.” At least, the Queen of Sheba flatteringly told Solomon that this was the case (1 Kings 10:8).

One’s status before God (being “blessed”) is not always expressed in terms of the individual or social conditions that bring what moderns normally consider to be “happiness.” So although it is appropriate to render 'esher as “blessed,” the rendering of “happiness” does not always convey its emphasis to modern readers.

Webster's Dictionary [2]

(1): (a.) Imparting happiness or bliss; fraught with happiness; blissful; joyful.

(2): (a.) Enjoying happiness or bliss; favored with blessings; happy; highly favored.

(3): (a.) Used euphemistically, ironically, or intensively.

(4): (a.) Beatified.

(5): (a.) Enjoying, or pertaining to, spiritual happiness, or heavenly felicity; as, the blessed in heaven.

(6): (imp. & p. p.) of Bless

(7): (a.) Hallowed; consecrated; worthy of blessing or adoration; heavenly; holy.

King James Dictionary [3]

BLESS'ED, pp. Made happy or prosperous extolled pronounced happy.

BLESS'ED, a. Happy prosperous in worldly affairs enjoying spiritual happiness and the favor of God enjoying heavenly felicity.

Blessed-Thistle. A plant of the genus Cnicus, sometimes used in decoctions, for a bitter.

International Standard Bible Encyclopedia [4]

bles´ed ( בּרוּך , bārūkh ): Where God is referred to, this word has the sense of "praise," as in  1 Samuel 25:32 , "Blessed be Yahweh, the God of Israel." But where man is in mind it is used in the sense of "happy" or "favored," and most frequently so in the Psalms and the Gospels, as for example, "Blessed is the man that walketh not in the counsel of the wicked" ( Psalm 1:1 ); "Blessed art thou among women" ( Luke 1:42 ); "Blessed are the poor in spirit" ( Matthew 5:3 ). See Beatitudes .

Cyclopedia of Biblical, Theological and Ecclesiastical Literature [5]

is a title given by the Church alone, and to persons who die in holiness. No individual bishop can give this title, which is granted in the Church of Rome only after a kind of proof, real or supposed, of the virtues and miracles of the person to whom it is given,