It’s funny how many life lessons one can extrapolate from a kimono – from the structure, the history of how the design came about, the type of cloth, the knots… it’s all really one massive exercise in coordination. You don’t really need Plum or I to point that out. So after sweating buckets over the right obi to go with the right kimono with the right sort of footwear, kanzashi and bag, you’d think you’re done with the hard part. Well, there’s the issue of what to do with that mop of cilia on top of your head – your hair. How are you going to do your hair? The ginko style isn’t going to suit everyone and unless you’re a real Japanese, this is going to look super costume-y on you.
Theatrical but no. Unless you’re really Japanese or Liza Dalby.
Big huge no-no there. There are easy escape routes like the chignon but if you’re non-Japanese and are wearing a kimono to a function, you don’t want to look just okay. You want to look great. That means getting the right updo, dammit. Thusly, I’ve regurgitated what I’ve learned about wearing your hair with any sort of kimono. I’m not a professional and God knows, there are days that I need help with my own hair but if I can save someone out there the trouble I went through in choosing what hairstyle to choose… why not? If the kimono was ice-cream, your hair is the topping that makes or breaks it.
Personally, I prefer the more polished look since the kimono is a garment meant for semi-formal to formal events. Unfortunately, having short curls puts me on the road towards ‘fun and flirty’ as opposed to ‘dignified goddess’. 
When choosing an updo to go with your kimono, there are a few things to consider:
1. Face shape
2. Hair colour, type and texture
3. Length of hair
4. Accessories
5. The function you’re dressing up for (Dinner? Open-air wedding reception? Prom?)
6. Your own personality and threshold for fussiness
Because this is going to be pretty long and lengthy… I’m just going to touch on face shape.
Before starting, get a jacket with a proper collar. This will help you see how your neck looks like, more or less, and how high you ought to style your hair without having to put on a kimono.
By now, you should know your face type is one of these types:
– round
– square
– heart
– oval
Depending on the shape of your face, there are certain parts of your face you want to elongate or disguise.
For round faces, choose updos that add focus to your crown and elongate your face. Side swept fringes and long, tousled bangs able to be tucked behind the ear will work well. The idea is to break the line of your cheek and jaw. Avoid slick backed styles and flat bangs as these just look awkward and have a tendency to look school-marmish. This is a nice example, even if it is Selena Gomez:
If you’ve got a squarish face, then you might want to consider adding some wispy (not unkempt) strands at the side of your face to soften the angles:
Heart-shaped faces have wide foreheads and cheekbones and a rather pointy chin. So choose updos that give the illusion of a smaller forehead and not-too-small chin. You could do a half-up-half-down hairstyle if you’ve got short to medium length hair. If you’ve got longer hair, you could pin your hair a little lower or to a side bun where it can be seen from the front. Try not to pile everything on top of your head or hide it. Wispy but arranged strands look nice so I’d suggest really experimenting.
If you’ve got an oval-shaped face, then you’re lucky. The common opinion is that you can pull off most styles with little consideration in choosing. I still say experiment because while the style might suit your face… There’s still the issue of hair colour and texture to consider next. (And you oval-shaped faced people thought you could get away easy…. XD)
~Blossom
I did try to find a more varied range of pictures but scouring the internetz for examples and trying to guess which face looks like which shape is harder than it looks. Much, much harder.
The Plum and Blossom 
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