One of the most influential architects in New England, he designed custom-made houses, government buildings, churches, schoolhouses, and private residences across the United States, and was popular among the Boston elite.

The younger Bryant received no formal training in architecture but taught himself industrial engineering and construction analysis as well as building design.

Bryant's career started at a time when few architects gained prominence in his hometown of Boston, Massachusetts, and he struggled to find commercial success in the profession.

He began informal training with fellow Boston architect Alexander Parris, who introduced him to neoclassical design and the use of Second Empire architectural templates.

Working primarily as a student in his early days, he quickly a member of Parris' newly opened architectural firm at the corner of Court and Washington Streets.

Bryant flourished in an era of what Roger B. Reed calls "unregulated building," when "traditions of craftsmanship were being replaced by products of the machine age.

Early in his career, he faced competition from larger firms that sought to monopolize the design and construction of buildings in the greater Boston area.

As a draftsman, he drew up minor additions and renovations to already established buildings in that city, and he struggled initially to find footing in the competitive field.

A common fault ascribed to Bryant is that he valued the art form of architecture over the commercial validity of his designs which proved to be counterproductive for his budding practice.

Bryant's firm attracted as partners noted architects such as Alexander Rice Esty, Edward H. Kendall, Albert Currier, Wilfred E. Mansur, Arthur Gilman and Louis P. Rogers.

In 1862, he worked with Gilman to design and eventually build Boston's Old City Hall, one of the first to be built in the French Second Empire style in the United States.

Bryant's only known commission in the American South is Thornbury, a plantation house built in the 1840s for Henry King Burgwyn in Northampton County, North Carolina.

[3] Together with Arthur Gilman, Bryant's firm devised the gridiron street pattern of Boston's Back Bay, laid out starting in the late 1850s.

On the other hand, larger, wealthier educational institutions like Harvard College paid him top dollar for their administration buildings—for which he was often asked to give input in their construction as well.

Many of his college buildings are in the Georgian style, constructed with wood and clapboards, their columns made of timber, framed up and turned on an oversized lathe.