When I started to deliberately dress vintage, one of the first "problems" to solve was: what on earth do I do with my hair? I say "problem", because I do actually rather enjoy playing with my hair ;) But I've had short hair for so many years that I'd gotten out of practice with the more elaborate forms of styling. The good thing is, I used to have really long hair and as a teenager was really into dressing it in all sorts of creative ways, so it hasn't been much of a learning curve to get back into it.
However, my current cut hasn't made life easy. I actually had grown my hair to about shoulder length, before in January this year (this would be before my style epiphany) I decided to go for a sleek, blunt bob with a fringe. Like so:

Not really the kind of vintage I'm into, although I did really like this haircut and received a lot of compliments on it. Since then it's been slowly growing, and it's about half way between my earlobe and my shoulder now. All one length, and not really long enough for updos.
I've been experimenting with it for a few weeks now, trying out curls and different ways to put it up - especially victory rolls, although those still turn out fairly pitiful considering the length! I'm a serious perfectionist when it comes to my hair (as well as everything else in life, let's be honest) and nothing's looked quite right to me until last week I finally hit upon the right way to curl my hair, and got it to look like this:

Which I'm really quite happy with! I've since been practising getting it to look more or less like this every day, and I've managed it for a couple of weeks now. I'm lucky in that my hair curls easily and I work from home, so I put the hair in rollers after having a shower and just leave it for a couple of hours before taking out the rolls and brushing it out. In the evening I roll it back into pin curls before going to bed, so the curls are fresh in the morning.
Other than that, I'm more or less just waiting for my hair to grow. I'm sure I'll do more experimenting with it the way it is now, and maybe hit upon a few other ways of wearing it, but I think I'll have to wait until it's longer to really discover some variety. At some point I think I need to have it cut anyway, not to take away any length, but to put layers in. With it all being one length, when it's curled it ends up being rather boxy, and that's only going to get worse.
The thing is, getting a hair cut simply for the purpose of curling and doing vintage dos seems like...rather a big step. ;) So I've been delaying it, in case I get tired of looking like this and want to go back to what you saw in the first pic! So far, so good - I love feeling feminine and the curly hair certainly gathers lots of compliments too, although they're more of the "ooh, lovely hair - are you going to a party?" variety. I just smile and say "no, I just felt like curls today". :)
Now that I've got the hair figure out, a new "problem" has presented itself: my wardrobe doesn't contain enough clothes that match the hair! I say "problem"...
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