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In 1887, Leonard served on a committee arranging graduation proceedings at the College, where classes had intermittently graduated in caps and gowns. He saw, however, that the gowns were of a pattern so shapeless they must be incorrect, and thus he began designing his own importing a gown from England quite different in cut and technical construction and altering it, embodying some American ideas as to fit and utility. Once complete, he placed an order for the Class of 1887 with Cottrell & Leonard, his familys dry goods and furs business based in Albany, N.Y
I have no idea how anyone does it with stilettos, although Ive certainly seen it done
If you go with a monochrome suit (where your shirt and tie match the suit), add a brown leather belt, brown watchband, and other small accents to your outfit
