Chronic Age-Related Fashionitis

I'm feeling a little boxed-in lately, at least in the fashion corner of my brain. I think part of it has to do with getting older and feeling more settled (one might say stuck; one could say that) in general, but I think part of it has more to do with self-expression: what I can, and can't, do and say, and where.

For example: there was a time in my life when I would dye my hair. Random chunks of pink and blue, terrible and homemade, would make appearances and then disappear a few weeks later. I wasn't invested in upkeep; I just liked having some little difference. I would wear 1970s neon-yellow maxi dresses with pink underwear underneath. I would do Big Daytime Eye Makeup, just for funsies, or dress in a Canadian approximation of a chola's outfit while studying. Just trying on different personas, you know?

Now, I feel like I've missed the boat. My office and my boss are both far from conservative, but my professionalism isn't usually the first thing people notice when my hair is dyed the colour of a Skittle. The women there with candy-coloured hair are that Funky Older Type: one is a beer sommelier with purple streaks in her gray, one has pink highlights in her salt-and-pepper, both wear Doc Martens, have small dogs, and carry custom-made laptop bags. Nothing wrong there, but not really my style, you know? As always, I want something a little more post-apocalyptic farm girl. Sleeker, more flattering and thought-provoking, less self-concious.

Maybe I'm complaining about aging out of my style; I'm increasingly aware of being "too old" for former go-to looks. Most of my friends are a few years younger than me, so they can still get away with looking like Hopie from Love and Rockets, or having semi-dreads or a pedophilic movember 'stache. Those who are my age usually work in creative fields - nobody cares if you're braless in a tank top when you're crunching out your third blog post of the day - and so I feel marooned on my island of Office Appropriate Clothing, trying to figure out if I can wear booty shorts to the office party or if I should stick with a pencil skirt.

Don't mistake this for wanting to dress in an outre style. I can (usually) tell what occasion demands which level of formality, and will try to be appropriate. I'm not going to show up at your wedding in a mini-dress, and I won't wear flip-flops to a job interview. This holds no matter what age I am, although I do tend to try harder to nail it than I did in my early 20s.

But it's the transition that's tripping me up. I feel like this is the reason so many women panic and cut off all their hair when they have kids: it's easy, but it also instantly identifies you as a mom. (How many older women do you know who have hair past their earlobes? It's an growing-up rite of passage.) I do not want to do this: I want to feel like my indomitable self even as I move into my 30s and beyond.

So I ask you: How can I reconcile my interest in weirdo club-inspired fetish fashions with a day job? Where can I wear bright blue wedge heels? Do I need to take out my gauged earrings and find some sedate studs? Where can I put the colour, if not in my hair? I know that, as I get older and my "job" turns into a "career," making bad clothing choices will affect me adversely; I also know that I don't want to bore myself into dressing like a substitute teacher every day until I retire. Where is the middle ground? And once I get there, what do I wear?