Entry 2 senses · 2 variants Webster, 1913 Coolly · Cool·ly · IPA /ˈkuːl.li/ a. adv. 01 a. Coolish; cool. 1. Coolish; cool.[Obs.] 02 adv. In a cool manner; without heat or excessive cold; without passion or ardor; calmly; deliberately; with indifference; impudently. 1. In a cool manner; without heat or excessive cold; without passion or ardor; calmly; deliberately; with indifference; impudently.