Maybe start with your budget?
As someone who's working his way up from easily affordable casual/contemporary to "tank", I'd say if you can afford it, go for a traditional, made-to-measure, 16-oz wool tartan kilt in some generic tartan (such as Braveheart, or the like) as your first. This may also cause you to want to buy all the other accessories at the same time, so you need to factor that in.
Other considerations include how often you want to wear it, and how you want to care for it.
I've been going about it the other way - starting with UKs and progressively getting more serious about style, quality, and personal value. This has also enabled me to buy more kilts early, and accessories as I feel I need them, learning more as I go. As of today, I have nine kilts of varying quality (knockabout to excellent), but I've probably spent enough now for two or three tanks.
Try stating your requirements (not necessarily here, I mean), and see what solutions fit.
Regards,
Rex, still in Project Manager Mode
At any moment you must be prepared to give up who you are today for who you could become tomorrow.
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