Practicing for those Awkward Hair Days

I've had my pixie cut for awhile now, since August 2011, and I've definitely contemplated growing it out on more than one occasion. I'll admit that the awkward regrowth period that I've heard a lot about, and have experienced whenever I push my salon appointment past the 6 weeks mark, has played some part in my failure to follow through with letting my hair grow out. But there are other factors too. I still like having really short hair. It's fun, liberating and so easy to live with.  I also feel like this haircut suits my life in NYC right now. But I am seriously considering growing out my hair (again). 

It has been 8 weeks since my last haircut and I'm kind of bored with my hair. As for timing, this is probably the best time to actually grow out my hair...I mean, maybe by Christmas all the awkward phases would be over with. And it will certainly be cooling down around here as we move into September so having a bit more hair would make sense from a comfort/warmth perspective. And I have been trying out some quick fixes for those inevitable bad hair days should I actually go though with this whole 'growing my hair out' thing, like hair bands, scarves, bobby pins etc. Anyways, who knows...I might just give in and go in for a small "trim" at some point or maybe I'll just wear a hat for the next few months and not think about it.  Silly but true.

Outfit Details:

Dress: Melora Dress, Anthropologie

T-Shirt: J Crew 

Shoes: Keds for Kate Spade