Green’s Dictionary of Slang

1. (Aus.) having thin, spindly legs, by extension physically unco-ordinated; thus lolly-legs, used of spindly legs and as nickname .

1905		Coburg Leader (Vic.) 10 June 3/3: Who is the young lady who waits at the corner of Collins street for a certain tram [...] Why does lolly-legs travel to Coburg second-class. Surely not to mash the boys.
1908		Sun (Kalgoorlie, WA) 2 Aug. 1/1: They Say [...] That an Arrow magpie has tickets on a local lolly-legged ganger.
1909		Richmond River Herald (NSW) 26 Mar. 4/4: Mr. E. Davison brought his son ‘Eddie’ home from the ‘Campbell’ hospital, Coraki [...] The broken thigh has been placed in plaster of Paris, and young Eddie is very proud of what he calls his ‘lolly’ leg.
1910		Sun. Times (Perth) 14 Aug. 1st sect. 1/1: They Say [...] That a lolly-legged bounder made an ass of himself at a, rinking shivoo. [...] That the elongated loon is now greeted with derisive yells.
1910		Sun (Kalgoorlie, WA) 5 June 12/8: They Say [...] That Shocking Charlie with the lollie legs is earning a reputation as a teller of tall tales.
1913		Sport (Adelaide) 11 Jan. 13/2: They Say [...] Tommy M. gets wild when you mention Empty House [...] Poor old Lollie Legs!
1921		Sun. Mirror (Perth) 27 Mar. 3/5: Queenie, we admire your taste, but say, who told you you looked well' in that black and white costume? It shows your lollie legs off.
1929		Cessnock Eagle (NSW) 19 Feb. 6/4: What an insult it would bo to the kiltie lassie for some of our long lolly-legged girls to appear without their stockings and secret padding on.
1934		Sun. Mail (Brisbane) 1 July 1/7: Players of to-day could not take hard knocks as well as players of a few years ago. They seemed to suffer from ‘lolly legs,’ and could not stand the game as it was played in the old days.
1941		Truth (Brisbane) 30 Nov. 2/1: The Madagascar galloper has real ‘lolly’-legs, and because of his unsoundness, he was not given any galloping last week.
1954		Truth (Sydney) 26 Sept. 31/1: Big, genial lolly-legged left-hander Bill Johnston.

2. in fig. use of sense 1.

1947

Newcastle Sun (NSW) 21 Aug. 10/5: If this policy were adopted [by the union], it would be better than encouraging the weakness of the ‘lolly-legged’ section with the aid of secret ballots.