I am going to suggest a different approach.

Why not start with a Utilikilt. You will be wearing it for a whole week and you may want to wash it. An original can be had for less than $150 and can go with anything you wear with pants.

When you win your challenge go for a full tank, and you will have a kilt for working and casual to boot. You can then pick the tartan you relate to or even just like with no restrictions.

I started with a Utilikilt and got used to wearing one and let those around me get used to me wearing it and now I have 8 tanks and 8 Utilikilts to rotate and wear as I like.