Entry 1 sense Webster, 1913 Dressy /drĕs'-ē/ · Dress·y · IPA /ˈdɹɛsi/ 01 a. Showy in dress; attentive to dress. 1. Showy in dress; attentive to dress. “A dressy flaunting maidservant.” — T. Hook. “A neat, dressy gentleman in black.” — W. Irving.