I turn 38 today. That’s not as momentous a number as 30, or as unsettling as 36, or as exciting (one hopes) as 40. Over the last few years, I’ve been getting into the habit of thinking of myself as a year older as soon as January hits; so, by this point, I have been mentally referring to myself as a 38 year-old for more than 6 months, which makes my actual birthday feel rather anti-climatic. I’m spending the week at home with my kids and husband, which is nice but not particularly conducive to deep reflection. Age is just a number anyway, right?

But I thought it would be fun to commemorate this otherwise unremarkable birthday on the blog by looking at how my style has evolved over the last 4 decades. Join me on a journey back in time, won’t you?

This is one of my favourite childhood photos; I don’t have any memories associated with it – I don’t even remember how old I was or where this was taken – but it so perfectly encapsulates my childhood. My parents insisted on cutting my hair short (despite my vociferous) protests for most of my early years; I seem to recall the rationale being that it would grow back thicker – a very Eastern European kind of rationale, but sadly one that my experience has disproven. The only tangible result was that, for years, strangers assumed I was a boy. One of my strongest childhood memories is of nightly prayers asking for long, blonde, curly hair like the heroines of my favourite fairy tales. Alas.

My style at the time could be best described as Soviet Block Tomboy Chic. I wore a mixture of homemade clothes and hand-me-downs from relatives in Western Europe. Since my female cousin was younger than me, most of those hand-me-downs came from my male cousin. I don’t remember caring too much about day-to-day clothes, but I was fascinated with grown-up clothes; I would beg my grandmothers and mom to let me dress up in their dresses and high heels, but it was a game more so than a form of self-expression. Oddly, I grew up thinking of myself as a tomboy, but I was always fascinated by older (teenage) girls – they seemed to know things I didn’t about being a “woman”, and I was desperate to find out their secrets, so that I, too, some day would transform from an ugly duckling to a swan.

My teenage years were deeply traumatic for a variety of reasons, so my transformative moment never really came. (At some point, I simply gave up waiting.) Not surprisingly, I haven’t kept a lot of photos of myself from that era; this was before the invention of the selfie, so there weren’t that many photos to begin with. I did manage to dig up a few less embarrassing ones (it’s all relative, though) so you could see the next stages of my sartorial journey.

After moving to Canada, my parents scraped by for a few years on minimum wage jobs so money was tight. My clothes came largely courtesy of thrift stores and the occasional K Mart or Mariposa splurge. Thrift in the late 90s was a different beast, at least in my experience. The middle picture above is a good illustration of what you might typically find in a thrift store back then: crappy plaid and 70s corduroy bell bottoms. Let me reassure you that I was not really into grunge at any point; I just didn’t really have a lot of choices.

Let’s fast forward a few years to my mid-twenties. Post-law school, I moved out on my own, and began living the single girl life in downtown Edmonton.

The picture on the left is so quintessentially mid-2000s “going out” wear, isn’t it? I’m pretty sure that’s a Forever 21 top, and those are definitely boot-cut polyester pants from Suzy Shier. As a baby lawyer, I wasn’t making much money, and fast fashion was as fancy as I could get – and it did feel fancy after years of shopping at Walmart. Clearly, though, my sense of style was pretty much non-existent, and certainly it was not a means for self-expression.

I’ll pause here to say that I still have the skirt I’m wearing in the middle photo. I bought it on sale at the Gap sometime in the early 2000s and for many years, it was the nicest piece of clothing I owned – it was silk, and it came from an “expensive” store; never mind that it wasn’t really in style then, or any time since. I’ve never been able to part with it because it was a kind of memento of a certain time in my life. I decided to wear it again this past weekend on a dinner date with my husband; it was a nice nostalgic moment. I’m not sure that I am now the person I thought I would be when I first bought this skirt, but I would like to think that my younger self would not be entirely disappointed with how things have turned out in our life.

The last decade of my sartorial adventures has been pretty well documented on this blog, so I won’t bother to recap it again. In a nutshell, the trajectory has been one of discovery (of the idea of personal style, of the fashion industry, or style as a form of self-expression), experimentation, and self-acceptance. I would like to say that I am completely indifferent to others’ opinions, but while that’s not entirely true, I think I have a far healthier relationship with external judgment than at any other time in my life. At 38, I am the most comfortable I have ever been — in my own skin, and in my clothes. And that’s a pretty good place to be.