His father Theodore was a successful dry goods businessman and was part of the planning committee for the World's Columbian Exposition.

His Dutch-American mother Sarah (née Van Doren) was a prolific painter and a member of the Bohemian Club.

Prairie Avenue was also the site of Chicago's most modern residential architecture,[2] including Henry Hobson Richardson's John J. Glessner House.

Howard Shaw met Frances Wells, his future wife, in the district's Bournique's dancing school on Twenty-Third Street.

MIT was one of the few architectural schools in the country at that time, closely following the rules set forth by the École des Beaux-Arts.

Shaw worked directly with emerging architects James Gamble Rogers, Alfred Hoyt Granger, and D. Everett Waid.

[citation needed] In 1894, Shaw established his own practice while finishing his work for Jenney & Mundie in his father's attic on Calumet Avenue.

[citation needed] In 1897, Shaw bought a one-third share of a 53-acre (21 ha) farm on Green Bay Road in Lake Forest.

Lake Forest had been a rural community to the north of Chicago, but was recently becoming a retreat site for the wealthy following the completion of the Onwentsia Club in 1895.

Shaw's house, Ragdale, is today considered one of the best examples of Arts and Crafts architecture and is listed on the National Register of Historic Places.

Shaw would meet with other Arts and Crafts architects, including Frank Lloyd Wright, in a lunch group known as The Eighteen, an early version of the Prairie School.

[citation needed] However, Shaw grew alienated from the Prairie School as he was a firm believer in the value of the old European architecture eschewed by the other architects.

[citation needed] Another early commission for Shaw was the rebuilding of the sanctuary of Second Presbyterian Church (Chicago, Illinois) following a devastating fire in March 1900.

[citation needed] As housing desirability for the wealthy waned in Hyde Park, it grew in the Gold Coast, and Shaw quickly became the prominent architect in this neighborhood.

The city sought to relieve this problem in 1912 by creating a "shopping center" where several businesses could operate out of one parcel of land.

Shaw collaborated with Edward H. Bennett on the design, a local architect that rose to prominence after co-authoring the Burnham Plan for Chicago.

Shaw was a trustee at the Art Institute of Chicago and was asked to build several additions, including the central courtyard.

In the United Kingdom, Shaw admired the work of Charles Rennie Mackintosh and Edwin Lutyens, who were combining Renaissance Revival architecture with modern design ideas.

These architects eschewed mass-produced materials typical of the Industrial Revolution in favor of the decorative arts movement.