The symbolism should be apparent. I used the word "Vagabond" in a font used often in association with travel ("Playscript"). The font gives the feel of being light-footed. Moving playfully. Like a Vagabond.
I added "Swag" to it to show that I sell shirts and travel gear and appeal to audiences in their 20s like me, and added some vagabond imagery to the text with the road swish at the end.
I realized I needed a Favicon for the website, and I wanted it to be recognizeable when small. So I used the swish at the end, shortened and rounded off to signify the road, and also share the "S" with the site's name, Swagabond.
Then I created a white-on-black logo set, seen below.