The Old Dominion Foundation, established by Paul Mellon '29, provided funding for the construction of Stiles and Morse, calling for the building of two "radically different" Yale colleges in order to reduce over-crowding.

[3] The college is built of rubble masonry in the style of pre-Gothic Tuscan towers, similar to those in the medieval Italian hill town of San Gimignano.

[6] The college consists of many single rooms and suites, and in a modern attempt to capture the spirit of Gothic architecture, Saarinen eliminated all right angles from the living areas.

Stiles' adjacent "twin" residential college Morse is architecturally similar, was built at the same time, and has an adjoining dining room with a common kitchen.

Architecturally, Morse and Stiles differ from older colleges by having more private space per student and the lowest ratio of natural light aperture to wall surface.

"[7] Saarinen continued: "We have made the buildings polygonal—their shapes derived in order to provide the diversity of student rooms, to answer the needs of the site, and to give variety and sequence of spatial experiences in the courts.

The college was once heated by a system that warmed the stone floors, but maintenance troubles led Yale to abandon it and install radiators.

[9] In fall 2010, the refurbishment of adjoining Morse College gave Stiles students access to a new gym, dance studio, and the Underground Crescent Theater.

During Arts Week, the college hosts study breaks and activities which have included painting pots for succulents, workshops in stop-motion animation, and open mic nights.