The 1890s and early 1900s formed a strange period at St. Paul’s, with students showing a mixture of conformity and rebellion. Boys still wore the narrow, pointed shoes of the time, stiff collars and scratchy woolen underwear; informal dress, even for athletics, was rigidly controlled; and hats had to be tipped to each master as he passed. Yet beards and side whiskers were grown, and as the years of the second Coit administration passed, drinking and smoking were common. For schools, and especially for the New England private schools, it was a time of unrest. Pictured above is a group of students playfully engaged in a bit of pretended debauchery; nevertheless, the decline in discipline and overall standards of behavior was a real issue within the School at that time.