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Simplified etymology
Swagger appears to have developed from swag, whose earliest meaning was “a bulging bag.” Swag later became a verb meaning “to sway or sag,” and swagger extended this physical idea to an arrogant or self-important way of walking or behaving.
Etymology
A frequentative formation from swag, 'to sway or move heavily.' The movement sense developed into an ostentatious strut and then into arrogant self-confidence. The dated adjective extended the same display to stylish or impressive things.