KIlt wearing falls into two large groups: People who treat the Kilt as a costume or almost  religious article, and people who regard it as a piece of clothing.  Your friend and advisor Wentworth Tradd is very firmly in the second group.

Let's start with a basic fact. If you haven't realized it already, there is a large industry devoted to making kilts and highland dress mystifying.  A large part of that mystery, or mystique, is just good marketing. A smaller part is tradition.

Presumably, you are not in Scotland or planning to wear your kilt there. If you are, why not find the first man you see wearing a kilt on the street and ask him.  For the rest of you, I can say that you can travel for days in Scotland without seeing a kilt at all and most of the ones you do see will be on people who don't wear one all of the time. That is, just folk like me.

I have found the book SO YOU'RE GOING TO WEAR THE KILT to be extremely helpful, and, since it costs about as much as a pair of nice kilt hose, you may want to get a copy.  This guide is not exactly a distilllation of that book, but it does contain some of the same advice.  Please remember that J. Charles Thompson (the author) has died and probably did so without seeing the great eBay kilt phenomenon. But I imagine he would be pleased, as much of his book is devoted to making the kilt accessible and affordable.

The cheapest way to get a kilt is to buy a woman's kilt and reverse the closure.  This does require a little bit of tailoring and might land you with something less than perfect, so you may want to spring for one of the economy kilts sold on eBay.  In either case, you should be able to start with the kilt itself for about $50 or less.  You can wear the kilt with just about anything else you would ordinarily wear: polo shirts, running shoes, sweaters, etc.  You will need some appropriate socks, though they only have to be the right length.  My recommendation is that you shoot for an optimal leg diameter- better large than small. Robert Burns' Ode to a Haggis  includes the line "his spindle shank a good whip lash" which sounds to me like the Scots' prejudice is in favor of strong calves. I mention this because ordinary over the calf men's dress socks look fine with a kilt so long as they don't make your legs look skinny. Joe Tex explained about skinny legs. Nobody wants them. You don't need to go further than that.

But legwear brings us to an important bit of kilt trivia. When King George went to Scotland in the mid 19th century to visit his more or less loyal subjects, he wore a kilt and wore it with flesh-colored tights.  This did not go over big with the locals. However, it did reflect a growing fascination with Tartan and things Scottish from that time period. The supposed great work on highland dress, the Vestiarum Scoticum, was forged during this time.  That's right. Two guys who called themselves the Sobieski Stuart Brothers wrote this book and passed it off as being several hundred years old. Why do you need to know this? Because almost all of the modern 20th and 21st century lore of kilts, tartans, and clans can be traced to this book.

Meaning what exactly? Meaning that  most of what you  hear about ancient tartans has been made up. Meaning you, as an American, can wear whatever tartan you choose.  No need to worry about  months and years of genealogy, just pick one you like.  Of course,  it is a good thing to  follow traditions, even ones that do not predate the Victorian era. So, if your name is MacDonald, or MacPherson or MacInnes, by all means you should try to get a kilt in the tartan that bears the same name. But if your name is Kinloch or Miller or Tradd, you can still wear most tartan patterns.

But we were talking about clothes, not ancestor worship.  You will want to consider a jacket that is designed to wear with the kilt. That would be a shorter one than your current suit coats.  Mr. Thomspon's book includes a chapter on altering  what he calls Saxon wear to  be worn with the kilt. You may find it cheaper to do that, or you may find it cheaper to  buy one on eBay.  But if you buy one, try to get the most versatile jacket you can find that will still be suitable for the situation in which you will be wearing the kilt.

If you plan to wear your kilt stalking or hunting, you should probably get a tweed coat, though you might want to wear your Barbour  raincoat with it.  If you plan to wear it to church and  funerals, the tweed will be acceptable, but  it will be too informal for dinner parties and balls. For those occasions you can get by with a navy jacket much as you would if you were wearing trousers. But if you want to be appropriately dressed for a wedding or a formal event, you will need a formal  kilt jacket.

There is another helpful guide on eBay that points out that you will need a sporran.  This is absolutely true. Chances are, you will need a sporran right after you get the kilt, or maybe after you get the kilt hose.  If you are careful, you will still have a few dollars left to put in it.  The sporran takes the place of pockets. It doesn't have to be fancy.  In fact, many situations call for a plainer one.  A simple rule is to make your sporran match your shoes, in color and in formality. If you are wearing your Nikes, you don't want the equivalent of a Black Tie sporran. But you would still need a place for your keys and your cell phone. A simple leather pouch will be fine.

Here is my recommended order of purchase for your kilt get-up:
The Kilt Book
The Kilt itself
Socks (hose)
Sporran
Kilt jacket
Belt
Skene dhu
kilt flashes
Hat or bonnet
other items (ghillie shirt,  dirk, second sporran or jacket, shoes, vest, etc.)

As soon as you get all of these things, get it on and get ready to talk about it. You will want to polish up your repertoire of kilt humor, of which there is aplenty.

Good luck
WT