There is no more glamorous city in Australia than Sydney. Ask anyone who lives there. It is the prestige place to live and work and have corporate headquarters. This annoys Perth, where the gravitational pull of ferrous metal is ever growing. Sydney is Tinsel-town to outsiders, but its prestige never fades.
The first paragraph of this essay is unequivocally a compliment to Sydney if each word is given its current meaning, but in earlier times it would have been seen as hovering on the frontier which envy shares with malice.
Glamour has developed oddly. Its current meaning is almost entirely favourable, even if tinged with jealousy. Some recent references in the Court of Appeal give a fair representation. In Chisholm v Pittwater Council & Anor  NSWCA 104 the Court said:
“…During the first part of the last century, Palm Beach was regarded as the “epitome of the simple, unspoilt life”. Later, Palm Beach acquired a reputation for “glamour”, and was regarded as a ‘place for the [very] wealthy’…”
The judgment is attributed to Meagher JA, Powell JA and Ipp AJA, but that sentence bears the stamp of Meagher JA.
In Union Shipping NZ v Morgan  NSWCA 124 at  Heydon JA, with laser-like precision, said:
“The defendant … said that all that mattered was the merit or weakness of any particular argument, quite independently of which court had employed it. Yet it was noticeable that the defendant, in its enthusiasm for particular arguments favourable to its position, constantly reminded the Court of the glamorous courts associated with them, like the United States Supreme Court, or the glamorous judicial names associated with them, like those of Jackson J and Frankfurter J, or even the glamorous academic names associated with them, like Kahn-Freund, Morris, Cheshire and North.”
Hodgson and Santow JJA agreed.
These references fairly catch the current sense of glamour, although the inverted commas around it in Chisholm suggest that the author well knew the gulf between its original and its current meaning. It’s all Sir Walter Scott’s fault. Glamour was originally a Scottish word meaning magic or sorcery, and its connotations were unfavourable. Burns used it in this sense:
“Ye gipsy-gang that deal in glamor, And you deep read in hell’s black grammar, (Warlocks and witches (1789))
Bailey’s dictionary (1721) does not have an entry for glamour, and neither does Johnson’s Dictionary (1755): but Johnson notoriously disliked Scotland. Scott is credited with introducing the word into literary use. In Letters on Demonology and Witchcraft (1830) he wrote:
“This species of Witchcraft is well known in Scotland as the glamour, or deceptio visus, and was supposed to be a special attribute of the race of Gipsies.”
(Deceptio visus, not surprisingly, is an optical illusion).
Later in the 19th century, glamour came to signify a magical or fictitious beauty; then in the 20th century charm; attractiveness; physical allure, especially feminine beauty. It is notable that charm is the hinge around which the shift in meaning swings, since charm can refer to an appealing character or to a magic spell.
By the middle of the 20th century the current meaning was established. In Terence Rattigan’s play Flare Path (1941) one character says:
“I’m going to pour it on with a bucket. If I can’t look like the screen’s great lover, I can at least smell like a glamour boy.”
Glamour and prestige have followed surprisingly similar trajectories. Like glamour, the current meaning of prestige can be fairly caught in recent decisions of the Court of Appeal. In Dawes Underwriting v Roth  NSWCA 152 Macfarlan JA said:
“Dawes offers insurance for a range of high performance, prestige , vintage and classic motor vehicles.”
In Fexuto v Bosnjak Holdings  NSWCA 97 Priestley JA noted that
“One element in what happened from 1988 onwards must have been Mr Jim Bosnjak’s increasing prestige in the bus industry outside the family business…”
(I wonder if it occurred to his Honour that ‘prestige in the bus industry’ was an improbable idea). In Citibank v Papandony  NSWCA 375, one term of the distributorship agreement provided:
“Distributor shall always use the Marks in such a manner as to maintain their goodwill, prestige, and reputation.”
The sense of the word is unmistakably favourable in each case. There is no hint that, at least until the late 19th century, prestige connoted magic, trickery, or deception. The OED offers quotations from the 17th to the 19th century in support of the original meaning an illusion; a conjuring trick; a deception, an imposture. It comes from the Latin præstigium: a delusion, and ultimately from præstringere to bind fast, thus præstringere oculos to blindfold, hence, to dazzle the eyes. Johnson has prestiges: “illusions, impostures, juggling tricks”.
During the 19th century, prestige acquired the secondary meaning “Blinding or dazzling influence; ‘magic’, glamour; influence or reputation”. Supporting quotations in the OED include this from Fonblanque (1837): “The prestige of the perfection of the law was unbroken.” and this from Sir William Harcourt (1898): “People talk sometimes of prestige.‥ I am not very fond of the word. What I understand by prestige is the consideration in which nations or individuals are held by their fellows”. It was not until the 20th century that its current sense was fully established. So this from W. Somerset Maugham (1944): “Though she didn’t much care for [modern paintings] she thought quite rightly that they would be a prestige item in their future home.”
Prestidigitation (originally prestigiation) is a close relative of prestige, but has not moved socially. It still means sleight of hand or legerdemain. The first use of it noted by OED is dated 1859: the very time when prestige was beginning to shift its meaning. It filled the gap left by its upwardly mobile relative.
And tinsel? It’s doubtful flattery. It originally referred to the treatment of fabric, especially satin, “Made to sparkle or glitter by the interweaving of gold or silver thread” (not bad), but later, applied to “a cheap imitation in which copper thread was used to obtain the sparkling effect” (not so good). But the traditional Scottish meaning was worse. In the 14th century it meant “The condition of being ‘lost’ spiritually; perdition, damnation.” In the 15th century, as a word in Scottish law, it meant forfeiture or deprivation. And in Bell’s Dictionary of Scottish Law (1838) there appears the entry:
Tinsel of Superiority, is a remedy‥for unentered vassals whose superiors are themselves uninfeft, and therefore cannot effectually enter them.
Glamour and prestige are examples of that exclusive club which includes obnoxious, panache, tawdry, sanction and mere. They are words whose meanings have shifted over time (that’s common enough): these words have changed meaning 180 degrees. Rarer still are words which have two current meanings which are opposite. But enough for now: I will let you figure out what they are.