[ win-ing-ist ]

  1. winning most often: the winningest coach in college basketball.

  2. most winning or charming: the winningest smile in town.

Origin of winningest

First recorded in 1970–75; winning + -est1

Words Nearby winningest Unabridged Based on the Random House Unabridged Dictionary, © Random House, Inc. 2023

How to use winningest in a sentence

  • "I'd like to stay the rest of the afternoon, if you don't mind," said Jane, at her winningest.

    Jane Journeys On | Ruth Comfort Mitchell
  • Then he turned and looked with the winningest smile at little Raymond.

    Tom Slade on the River | Percy K. Fitzhugh
  • "You do not come to see all your friends," she said, with her winningest smile and her most bird-like voice.

    Gordon Keith | Thomas Nelson Page