I admire your style and your free spirit so much.  I’m more like that in some ways today than I ever have been, but I still kind of have a problem.  First off, I’m not particularly pretty.  I’m actually pretty funny looking.  And I’m 30 now, which adds some cultural expectations that I’m not sure it’s appropriate for me to attempt to contravene.  I want to wear the things I find fascinating and I want to do bold things with my makeup and hair — but I also don’t want to be ridiculous.  Help?

Meg


Dame Edna.

Dear Meg,

It’s rare to hear from someone who is closer to my age group (I’m 28, just 2 years shy of 30!). :) A few months ago I did a similar article on the subject on looking age-appropriate. It all starts with our mother saying, “You’re a big girl now…” and before we know it, we’re expected to act like a certain number. If you accept this, then there isn’t much you can do. But if you don’t… what IF you don’t…??

What if we lived in a world that allowed us to be anything we want to be as long as we’re not hurting anyone? What if there was a place where looking different wasn’t such a crime? What if our age didn’t come with a description of how we need to behave in order not to be made fun of? Let’s dream a little: in your ideal Candyfuture, at the age 50, are you settled down and leading a suburban life? Grand kids, a husband, a job where you’re expected to look a certain way? We all feel the need to fit in sometimes – there is nothing wrong with wanting stability and normalcy in your life. But are you fitting in and finding enjoyment in it? If the answer is yes, then you’re fine. Have fun with your hair/wardrobe on weekends, throw an occasional costume party and enjoy yourself! Having a more accepted ‘exterior’ is how most people live, it doesn’t mean you can’t have fun in the safety of your own home!

However! If you fail to picture yourself as anything but a lilac-haired, umbrella-collecting character at 65, then it’s a different story.

I often get asked what I think I will look like when I’m older. “Exactly like I do now, but 10x amplified” is what I say. My dress style a compilation of all looks I’d gone through through the years, stacked on top of each other like a pile of hotcakes. The further I go, the taller and more diverse the pile grows. My life experiences and how I interpret them through clothes is what makes me, me – so in a way I can’t wait to see me at 50! If things progress how I expect them to, it certainly won’t be boring. And when I’m really old – on the outside, never on the inside – and rocking a walker at 80, I’m pretty sure I’ll have powder-blue hair and rock that, too.

Will I look ridiculous? Probably. Too bad I’ll be too busy having fun to care.

Whew – what a bit of perspective can do sometimes, eh? The big 3-0 is only the beginning. You don’t have to make the decision right now – you still have a good 5-10 years to wear short skirts, sexy makeup, and not care!  Think of your 30s as a grand entrance to a ball – and you are going to have a ball no matter what!

As for your ‘not pretty’ question. The whole idea of fun is to try to look our best, or what we think is best. Doing so will give you confidence to put it out there, and translate flaws into uniqueness. I’m a big fan of LaRoux‘s; she may not have a model face but she knows how to work it and that makes her attractive.

Deerlings: how do you picture yourself at 50? 60? 80?

Got a question for Doe Deere? Get in touch at doedeere @ gmail.com.