In 1886, construction began on the east wing of the Academy, as the Sisters had quickly outgrown the 1871 building. There is evidence that the Academy had expected the growth of the school to continue, and had requested that Vereydhen plan for an additional wing. Architect John Teague oversaw the construction of this part of the building, and actually signed the 1886 plans and drawings.
Teague was a well known English architect, who did a great deal of work in Victoria. City Hall, the Freemason's Meeting Hall, several hotels and the little Church of Our Lord, which still stands across the street from St. Ann's, are some of the prominent designs associated with his name. He had worked for the Sisters on a convent in Nanaimo, previous to the 1886 addition in Victoria.
The style of architecture was, of course, based upon Michaud's 1871 wing, and in keeping with its French Canadian influences. The 1886 additions created a very horizontal, symmetrical building that focused visitors' attention on the main entrance. Many features were neo-classical, meaning that they were influenced by the great architecture of the Ancient Greek and Roman world. The triangular overhang that sits over the entrance is known as a pediment. This type of entrance, in a pavilion design, made the building into a monumental piece of architecture, divided into sections or bays, by the rows of attached columns called pilasters. The windows, with a slightly rounded frame at the top of the pane, sat within these bays. The parapet at the roofline was balustraded, or given a railing, with five dormer windows to match the 1871 wing.
While the original wing had been very vertical, with the design emphasizing the height, the additions gave the Academy mass and horizontality. The school stretched across the south end of the grounds and planted itself in the ground with the coursed base of the pilasters, which were divided into block-like sections. The windows were underlined with a string course, a thin band running across the front of the building, to give a sense from the outside of where the floors were divided on the inside of the school. These features helped to give the brick architecture the appearance of stone, the material which would have been most popular in Quebec.
The new entrance block was capped by a bell tower, with a cross at the very top. This became a major feature of the Victoria skyline, and can still be seen over the treetops from several blocks away. Having such a focal point was another design motif that linked this building to the French Canadian origins of the Sisters. It is clear, comparing St. Ann's Academy in Victoria with the Mother House of the Sisters in Lachine, Quebec, that this particular combination of ecclesiastical, institutional and Classical Revival architecture was also popular in Eastern Canada.
At the time of the 1886 construction, St. Andrew's Cathedral was moved across Humboldt and connected to the rear of the new addition, in order to be used as the chapel. To add continuity to the overall appearance, both the 1871 and 1886 wings were repainted to give the texture and appearance of sandstone, using an amber toned paint embedded with sand grains.