Virendranath Chattopadhyaya was the second of eight children born to Aghorenath Chattopadhyaya and his wife, a Bengali family, in Hyderabad. His siblings include Sarojini Naidu and Harindranath Chattopadhyaya. Virendranath was also known as 'Chatto'.

Virendranath travelled to England in 1902 to study law and compete for the Indian Civil Service (ICS). He failed the ICS exams twice and enrolled in Middle Temple. In 1903, he was living with an English woman in Notting Hill under the names Mr and Mrs Chatterton. The couple parted ways in 1909.

Virendranath was rejected from Shyamaji Krishnavarma's India House scholarships in 1905 but was intimately involved with the India House organization in Highgate. Following the murder of Sir Curzon Wyllie by Madan Lal Dhingra in July 1909, Chattopadhyaya sent a letter to The Times in support of Savarkar's right to freedom of speech in response to the assassination. He was then expelled from Middle Temple. Virendranath was a close friend of V. D. Savarkar in London and visited him frequently in Brixton Gaol in 1910. To avoid a warrant for his arrest, Virendranath went into exile in June 1910 by moving to Paris.