Just my 2 bits for the OP:

I served 8 years as a SWCC, so I RARELY wore a dress uniform or even tropical whites for that matter, so my opinion is a bit skewed. Also, in the past I've said that I'm not a fan of wearing minis or medals unless in full uniform while on duty and UOD requires. My opinion on that may be changing.

1) Ditch the dixie cup--or as we referred to them "Targets"
2) Tropical white shirt with a Edzell tartan kilt would look great in my opinion.
3) I'd leave the gaiters and boots behind and wear matching hose and nice shined leather shoes
4) It was your service and your desire to honor those others who have served. Let that guide you.

Thanks for your service, shipmate!