Pitt is best known as one of the outstanding architects of the "boom" era of the 1880s in Melbourne, designing some of the city's most elaborate High Victorian commercial buildings.

He worked in a range of styles including Gothic Revival, Italianate, French Second Empire, and his own inventive eclectic compositions.

In 1875 Pitt was articled to the architect George Browne, who was something of a prodigy himself, designing the Rupertswood mansion, Her Majesty's Ballarat and The Theatre Royal on Bourke Street in the early 1870s, when he was in his mid 20s.

The elaborate dome-like Mansard roofed pavilions, the each topped by crown-like cast iron capping, still makes a striking statement in Spring Street, and the sumptuous marble stair and elaborately ceilinged circle foyer are the finest Victorian era theatre interiors to survive in Australia (the auditorium itself was replaced in 1922).

His largest and most ambitious commission followed soon after, the Federal Coffee Palace at the south-west corner of King and Collins streets.

His other greatest work in Collins Street is the lavishly detailed Gothic Revival Stock Exchange (1888), complete with rose window, spire and vaulted 'Cathedral Room' on the ground floor.

[2] He kept his practice going however, and began a second career, designing a range of building types in the then fashionable styles, specialising in theatre and industrial projects.

[7] Pitt worked for the Collinswood-based Foy & Gibson for much of his professional life, starting in the late 1880s, and this also sustained him after the crash.

These were designed in a range of styles, though the Tivoli was by far the most inventive, featuring a red brick facade with exotic Moorish horseshoe arches, topped by a globe.

His work even extended to one of the first luxury cinema buildings in Melbourne, the Hoyts De Luxe in Bourke Street (1915, facade remains under later cladding).

He was a staunch protectionist and a vocal supporter of the Australian Federation Movement,[10] and acted on these views while a member of the Victorian Parliament.