2. A swag can be an ornamental curtain draped in a curve between two points, or something that hangs down. 3. A swag is also an ornamental wreath of flowers or fruits. 4. Swag may refer to an unsteady swaying or lurching movement. 5. In slang terms, it sometimes means stolen loot.6.o have swag is to have confidence in yourself for example to say a boy has swag it means he is wearing the latest trend he is confident in himself and he has everything in on … e whole package it is simply a word teenagers use to compliment or boost self esteem with.