Nothing wrong with any of that. That's pretty much how I do it every day.

Here's an old pic, but it's already in photobucket so it's handy.

And yes...I do wear a Navy ballcap with my kilt.

Lately I've been wearing Bates cold-weather boots. My neighbors think I'm nuts to wear a kilt in the snow. I don't think they understand how much heat a kilt will retain.

Don't be so hard on yourself...so you have a bit of a gut. So do a lot of us. Most efforts(such as loose and untucked shirts) to camouflage it actually accentuate it. Just be a Gentleman of Substance and don't worry about it.