Early reviews looked unfavorably upon Jewett, even dubbing it "Pilcher's Crime" and by 2002, a host of issues plagued the dorm, leading to a $21 million renovation.

[5] By 2002, Jewett hosted a spectrum of problems, highlighted in Vassar's alumnae/i magazine as including an elevator that simply does not stop at the second floor; balconies you can never reach; a mezzanine-level bathroom for residents of the third-floor tower area, complete with stalls so squeezed that those of all heights bruise their kneecaps when they sit to use the facilities; and a stairway tightly wrapped around a nine-story elevator shaft that no longer comes close to meeting fire safety codes.

[9] The dormitory, constructed from brick and stone, consists of a four-story U-shaped main body with a nine-story tower built ostensibly "to help campus water pressure.

[7] Historian Elizabeth A. Daniels notes that while Jewett's design is "generally Tudor in spirit",[2] it contrasts with the rest of the dorms on the quad which are Elizabethan in style.

[9] Instead of using stone for decorative exterior elements including trim and faces, as was common at the time of construction, Pilcher utilized terracotta.

[12] Other external features include a pitched copper roof with a low slope, limestone-surrounded entrances, crenellations, and light red brick.

[13][14] According to architectural writers Karen Van Lengen and Lisa Reilly, the tower's presence "created a more monumental and less homelike impression than that of its neighbor, Josselyn" which they speculate may have earned the dorm its nickname, "Pilcher's Crime".