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Jamie's Version
#1 Very Casual

Notes: Here I am wearing the kilt as the equivalent to a pair of jeans. This is my hiking outfit. The rolled down hose can be pulled up in the cool of the morning or to protect the legs when going through a patch of prickly undergrowth. My sporran is a simple one that doesn't look out of place when worn with hiking boots. My head gear is chosen for its practicality above all else. My favorite variant of this sort outfit is to wear a REI or other good quality long sleeved hiking shirt with a fleece zip up vest. This gives you the most options for keeping warm or cool as the day progresses. A nice rugby shirt goes very well with this look and for hot weather so would a t-shirt.
#2 Casual / Festival wear

Notes: For the moment ignore the pith helmet and fly whisk in my hand and imagine this outfit is worn with a khaki tam or balmoral bonnet (which is what I wear with it most of the time). This outfit takes inspiration from the uniform of the 1930s-1940s Black Watch regiment. It isn't an exact replica costume and I don't want it be. As a casual day outfit it uses simple brown leather belts, shoes, and sporran. A safari shirt (either long or short sleeved) is a great nice looking casual shirt that works well with kilts because it echoes the look of the Scottish highland regimental uniform. The red flashes, even though there is no red in the rest of the outfit, work for the same reason (ditto for the sporran). It is military fashion that was adopted into civilian attire. A set of red flashes works well with a variety of tartans for this reason.
Now as for the pith helmet and fly whisk, there are some who do not want to see the kilt ever worn as a costume (think for a moment of the gross stereotypes perpetuated by the typical cheap "Scotsman" costume one can buy for Halloween). Likewise they dislike the psuedo "Jacobite" look sported by many at highland games. Now I think that the "Jacobite" look is fun (even if it has much more to do with with Hollywood and Romance novel covers than actual history) but I as I attend Highland games in Summer in California I wanted an outfit that would be cool and offer me some protection from the sun. So my standard attire at these events is to wear this outfit that tips its hat (or helmet) to the Highland regiments stationed in tropical climes. I fully admit to the pith hemet being a bit whimsical or theatrical, but then again so I am. Now I have even worn this very outfit as a Halloween Costume. Trading in the fly whisk for a butterfly net and with my wife dressed as a butterfly we made a splash at our Scottish Country Dance Halloween party. I feel that I was successful integrating my kilt into a Halloween costume while still being respectful to the kilt. I think that our sense of heritage can and should include a little bit of fun.
As for the fly whisk? Well I do have small children to keep in line...
#3 Sporty

Notes: Here I am wearing the kilt as the equivalent to a pair of Docker style pants for an afternoon BBQ or out to the pub with friends. Polo shirts look very smart with kilts. Generally one wears brown leather accessories for day wear. However some late afternoon or evening events require a smart but casual look, also some tartans don't work very well with brown leather accessories. I am wearing black shoes and belts, but I make sure to use a simple black sporran. Likewise even though I am wearing a belt with a waist plate (which really is a more formal look) using a green enamelled one instead of a bright chrome or silver piece makes it less formal (a dull pewter or brass waist plate would have a similar effect). This particular type of outfit has great versatility as I can wear my tweed crail jacket with it to dress things up, my short waisted "motorcycle style" leather jacket to dress things down, or a "wooly pully" commando style sweater that would fall somewhere in between.
#4 Day wear

Notes: This is the sort of outfit I would enjoy wearing for a a long stroll in the park or out shopping. Turtlenecks and kilts go together like bread and butter. The wonderful thing about a turtleneck is that it can elevate a less formal look and also makes a more formal look less so. My sporran, sporran belt, and shoes are a mix of brown and black leather, which isn't traditional but makes for a fun and casual look. The use of a brown jacket, turtleneck, and pocket square carry the day wear colors theme. I am wearing oatmeal hose which are a great compliment to most tartans especially for day wear.
#5 Smart Day wear

Notes: I am again using brown leather accessories, but I am wearing a fancier fur sporran. The waist coat and tie make the outfit look very nice, but the tan/oatmeal shirt, hose, and jacket gives a casualness to the ensemble. The dark brown waist coat makes for a bit of contrast to all the tan hues. The deer stalker hat is quite authentic for highland attire, comfortable, and one of the few Scottish hats that offer any sort of sun protection for one's face and neck. This is the sort of outfit I would wear to a morning wedding, party, or church service.
#6 Dressy

Notes: In my opinion the most useful jacket one can own for kilted attire is a simple tweed Argyll or crail. Much like a tweed blazer works equally well with jeans or dress slacks the tweed kilt jacket serves one well in a great number of situations. This outfit is one I would wear for a late afternoon or early evening event, such as an afternoon wedding. I use back leather accessories and versatile mink fur sporran (this type of fur sporran with a leather cantle actually would work for almost every one of the outfits I am showing that use black leather accessories). My shirt is a businesslike light blue with a dressier white collar. The red tie, pocket square, and flashes "pop" from the dark blue of the waistcoat and hose. A more elaborate watch chain with fob is adds a touch of class. Now this is just my opinion, but I have always found the glengarry bonnet to be much more formal looking than the balmoral. So I use mine for that finishing touch when I am trying to look really sharp.
#7 Semi Formal (suit equivalent)

Notes: My black Argyll/Braemar jacket and a white shirt make this outfit more formal than the previous one. Instead of a waist coat, I chose a belt and waist plate (but not a bright metal one as those I reserve for more formal attire). Also I have traded the red accents for more muted green, blue, and black giving things a more subdued modern look. I have switched my shoes for more formal leather soled ones. This is what I might wear out to dinner or an evening wedding or party.
#8 Semi Formal (Tuxedo equivalent)

Notes: Some evening events are "formal optional" which can be a bit awkward to figure out how to dress for. There will be people in dark suits, others in sport coats, and a few in tuxedos (but not tail coats). One doesn't want to show up one's boss who is wearing a tuxedo by wearing a Prince Charlie, but at the same time one wants to dress up and make a statement. This can easily be managed by wearing a black argyll jacket, with a dress (tux) shirt, bow tie, and either a three button waistcoat (like as worn with a Prince Charlie coatee) or a belt with fancy waist plate which is akin to wearing a cummerbund. In this outfit I have traded my all black mink sporran for a fancier metal cantled calf skin sporran with a matching waist plate. Beyond these and the dress (tux) pleated shirt, and black satin bow tie this outfit is the same as the previous one.
#9 Formal (Black Tie)

I am wearing my PC style coatee in the modern fashion with white hose and fly plaid. Traditional diced/argyll hose (or even just solid color hose) would also look very smart. I have traded my formal dress shoes for ghillie brogues. Personally I only wear a fly plaid for special occasions. Some people wear a belt/waist plate as well as their waist coat, but I'm not fond of the look. Whether worn in classic or modern style a PC always looks sharp.
#10 Formal (White tie)

Notes: While the hose I am wearing are perfectly acceptable, diced or argyll hose would be the perfect finishing touch with my sheriffmuir doublet. I also think that a formal doublet is the one the type of highland attire where buckle brogues would be the very best choice for footwear, though ghillie brogues are certainly acceptable.
-See it there, a white plume
Over the battle - A diamond in the ash
Of the ultimate combustion-My panache
Edmond Rostand
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