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Singapore Democratic Party (SDP) assistant secretary-general John Tan Liang Joo, 47, was sentenced to 15 days' jail.
Activist Isrizal Mohamed Isa, 33, and full-time national serviceman Muhammad Shafi'ie Syahmi Sariman, 20, were each sentenced to seven days' jail.
Justice Judith Prakash also ordered each of them to pay $5,000 in costs to the Attorney-General's Chambers (AGC), as well as for other expenses it incurred during the proceedings.
But the trio are not starting their jail terms immediately.
Justice Prakash gave time for Isrizal to settle his personal affairs and Shafi'ie to complete his basic military training.
They are to surrender themselves on Dec 12.
Tan was given until Dec 18 to start serving his jail term. He told the court he is considering an appeal.
In pronouncing the sentences yesterday, Justice Prakash - who found the trio in contempt of court at a hearing on Monday - noted that they did not apologise or withdraw the insinuations made about the courts when they were given the opportunity to do so.
'(Given) the fact that none of you has shown any contrition, but maintained what you did was justified and was fair criticism when it was not fair criticism - and I will explain in my judgment why it was not fair criticism - I think there is no alternative in this case but to impose a sentence of incarceration,' she said.
The Attorney-General's Chambers initiated contempt of court proceedings against the men for having 'scandalised the Singapore judiciary by publicly wearing identical white T-shirts, imprinted with a palm-size picture of a kangaroo dressed in a judge's gown, within and in the vicinity of the New Supreme Court Building'.
They wore the T-shirts between May 26 and 28 at the Supreme Court.
This was when they were at hearings where Justice Belinda Ang assessed defamation damages that the SDP, its leader Chee Soon Juan and his sister Chee Siok Chin had to pay Prime Minister Lee Hsien Loong and Minister Mentor Lee Kuan Yew.
On Monday, Deputy Solicitor-General Jeffrey Chan sought stiff jail terms for the trio, saying that the worst insult anyone can level against the judicial system is to call it a kangaroo court.
This is generally understood to mean a court that is characterised by unauthorised or irregular procedures, or sham and unfair legal proceedings.
Mr Chan said the men's refusal to apologise reaffirmed their contempt of court. He urged Justice Prakash to pass a sentence that would denounce such a show of contempt and deter others from acting in the same way.
Asked about the jail terms yesterday, Senior Counsel K.S. Rajah noted that they were stiff sentences.
He said: 'They must now realise that being in contempt of court is serious business. Whether you use a symbol or a word, if it is universally recognised, then you must pay the penalty.
'The judge gave them an opportunity to repent and those chaps did not. Where a judge indicates the way she is likely to decide, you must recognise the fact that a chance is being given...There was a door open to them and they were defiant.'
In 2006, SDP leader Chee became the first to be jailed here for contempt by scandalising the court. Prior to that, only fines were meted out.
He was sentenced to one day in jail and a fine of $6,000 for offending statements about the judiciary, for which he did not apologise. He did not pay the fine and so spent seven more days in prison.
