@pumpa-cat
My first sloop is my main ship. The Wailing Meg. I use it for most sessions. I consider it my adventure sloop. I've called it by that name and used the same cosmetics for a long time even before captaincy was introduced. Probably 80% of my milestones have been earned sailing it.
My second sloop is athena themed. The Onyx Ghost. Most of the time that I'm doing guardians of fortune pvp, I use it. It's been almost exclusively a guardian of fortune ship. Cmdr Shepherd sails with me to help fight the reapers.
My third is a servant of the flame ship. Death's Visage. It is exclusively used for servant of the flame pvp and decked out with bone crusher cosmetics.
I've had another sloop in mind but haven't gotten around to making it. I was going to call it the Planet Express ship. It would be green and used only for merchant voyages, and I would have a monkey named Guenter accompany me on my voyages.
I had an idea for a second brigantine as well. Sometimes I don't use my ship during sessions but instead use a rowboat and leave my ship completely behind. I considered playing this way on a brigantine named the Mary Celeste. Named after an actual brigantine found adrift and deserted in 1872. Any crews that find my ship would find a deserted ghost ship while I'm off doing my thing. Hopefully they would understand the reference and have a good laugh.
As you can see, any ship I make beyond my original has a theme. My first ship has done a ton all across the board, but my others stick to an idea.
The Wailing Meg represents my pirate as a whole, associated with his identity and history.
My other ships represent something from the larger world of sea of thieve's and my pirate playing his part in something bigger than him, or as a reference used in humor.