Vanderbilt Hall on Yale's Old Campus was completed in 1894. It was designed by Charles Coolidge Haight, an architect from New York City who also designed most of the buildings at Columbia College's old campus on Madison Avenue.
Haight designed many buildings at Yale. Phelps Gate followed Vanderbilt Hall in 1895, and Phelps Hall in 1896. Yale's collegiate Gothic look is more often credited to the better-known James Gamble Rogers, but many of Haight's buildings survive.
This is a good place to see the contrast. The 1901 photo shows the tall dorm with a tinted sky and cobbles, and the modern photo shows a lamp post and a stone gate post where the old street scene was.