The red Stewart Royal is probably the best known of all tartans. It is an eye catcher.
  It is a universal tartan and also used for kilted skirts..
 

Royal Stewart. Lugano, Switzerland
 

Rome. Douglas Green Modern tartan

Lugano. Douglas Green Modern
 

Campbell Ancient in Ticino, Switzerland 

1. Start with the upper part of your body. You need a shirt of some kind. It should always be SOLID coloured (never mix different patterns) and of course in harmony with the colours of your just received kilt and kilt hose (not necessarily the same colours, but matching).
To my opinion a shirt should also always be tucked in when wearing a kilt. 

2. Put on your kilt hose (or appropriate socks). Kilt hose are by nature over-knees. Fold them down so that the top is 1-2 inch below your knee cap.

3. Put on your shoes. Yes, it is easier to get your shoes on before the kilt. They should preferably match the colours of other leather items you might wear.

4. Now the kilt. Put it around you. The pleats shall be at the back of course. Now fasten it to your body by means of the strap in your right hand and the buckle to the left.
   Take the strap through the little slid next to the buckle and fasten it. Then fasten the over apron. For that you have one or two buckles at your right hip.    Finally adjust the kilt horizontally. I normally use my thumbs on the belt straps at the back as a first indicator.

5. The buckles and straps will prevent your kilt from disgracing you. But if you want to supply with the belt it is time for it now. It does not have to go through the belt loops, by the way, because they are originally intended for the sporran strap. But why not? I always use them for my belt. And with very, very few exceptions I always wear a belt with my kilts, even if it is for pure decoration.

6. A sporran shall hang on your front. But don’t have it hang too low. About 7-10 cm or a hand’s breadth below your belt should be the maximum.
   As said earlier, some men prefer to have their stuff in a belt pack or in the pockets of their wind breakers, photo bags or whatever rather than using a sporran. I myself will on most days wear a sporran.

7. Take a look into a mirror. Should your kilt be lowered or heightened a little bit? Is it centered correctly? Make some adjustments if necessary.

You are ready to leave!

Do you think it was complicated? It isn't. When you have tried a few times you'll realize that getting inti the kilt is faster than getting into trousers.

What about?

O yes, of course, the underwear question. I didn’t mention, because it is your private business. No law forbids you to use underwear with your kilt and no one tells you that you must.

No reliable statistics to the subject are available but it is to believe that all men wearing kilts have at least once tried to go without underwear.  

What you do always, never or from time to time is all up to you, but whatever you choose you better keep to yourself and your wife or girlfriend. If asked by others, and you will, never give a definite answer. The "secret" may very well be the reason why the kilt is still so very much alive.

If you wear your kilt the way most people seeing you expect you to, it is called going commando or regimental. In kilted Scottish regiments underwear was (is?) not allowed and it was sometimes checked by means of a mirror whether the soldiers obeyed to rules or not. If not they were punished.

How to sit (down) wearing a kilt?

One of the advantages of trousers is that you can sit and sit down without any risks of exposing yourself. After shorts have become longer and with narrower legs (and thus more uncomfortable) the same applies to them.
   Women seem to know per instinct, even if they almost never wear a skirt, that when, some precautions must be taken and how to do it.
   With a kilt it is the same, but men don’t have the instinct feeling of how to do. 

As you sit down, smooth the pleats of the kilt beneath you to prevent the kilt to twinkle but foremost to secure that you are sitting on the kilt fabric, not directly on the chair.

No normal man wants to show his underwear or just part of it and even less his genitals, should he be going regimental.  Therefore, when sitting, keep at all times your legs together; you should never spread them. If you do, make sure the apron of your kilt is between your legs.

Sitting with crossed legs might be possible, but better cross your calves than your thighs. Especially as you cross your legs pay a little bit attention. 

Come in mind that people might be more than average interested in you and that some will constantly keep an eye on your legs and movements (in restaurants, on benches in parks etc.)

What about wearing a kilt when it is windy?

Mostly your kilt will stay perfectly down. But of course there is no guarantee that your kilt cannot be taken by the wind. On your front the sporran will in practically all situations give you the needed protection. On your back it can under circumstances be a little bit more difficult, but keeping your hands at your side should effectively prevent the kilt to be around your ears and should it blow up it is normally just a question of a second or two, which is in most cases too little for anybody to really recognize. 

Don’t worry. An exposure would require a staircase being as steep as ladder and that someone was climbing up directly behind you.

What if I, after all, do something wrong?

Here we talk casual wear, not national dress. Accordingly you can and should forget about most and often rigid rules, apart from a general proper appearance. And honestly, how likely is it that you shall meet an expert? And should you, how likely do you think it is that he should tell you?

If not allready, and should you like to, do it. If you already have got your kilt and accessories but have not yet been out in public, do it.     

Just after a few steps you'll realize how comfortable it feels wearing the kilt. And along with you realizing that kilt wearing is a non-event, your self confidence shall grow.

Soon your biggest problem might be, that kilt wearing is addictive. And you are, after all, not supposed to wear the kilt all the time. Here you must be man enough. Trousers do have their advantages, too.

Happy kilting!