I got the idea for this post from Reddit (one of my favourite procrastination destinations on the web at the moment — welcome to 2010!), and thought it would be fun to attempt to chart my own style evolution here — mainly for entertainment purposes, but don’t be afraid to try this at home. The actual work was harder than I anticipated, because while this blog does memorialize for posterity my bad fashion choices, there is an over-abundance of such choices to consider and very little to connect them into any semblance of a coherent narrative. Simply put, my style has been all over the place in the last decade. With that said, I tried. And the main lesson I learned from the exercise was that I’m actually getting better at getting myself dressed. Not a moment too soon, considering I just turned 36.

Let’s start our journey together (you’re still with me, I hope?) back in 2009. It’s an arbitrary year from a sartorial point of view, but a necessary starting point practically-speaking; I don’t have any older photos on my current hard drive. You’re not missing much, in any case. I spent my teens dressed in Walmart and thrift clothes (back then, that meant 70s polyester collared shirts and mom pants, not designer anything), and my early and mid-twenties dressed in the cheapest mall couture I could find. I only really started to get interested in fashion towards 2008, when a friend introduced me to the joys of consignment shopping.

So, 2009. Picture it: I was living downtown, had recently started a new job, and was about to conclude a long-distance relationship — happily, by getting engaged and having my then-boyfriend move back to Edmonton. I was an avid reader of fashion magazines, but definitely felt alienated from the whole fashion world in my relatively small provincial town. (The Edmonton scene was definitely different back then; it was a HUGE deal when the first Coach store opened here, back in 2008 or so.) My outfits were pretty snooze-worthy:

Like every other person who felt invisible to the fashion world back then, I started a blog in 2010. At the time, I thought it was a very avant-garde thing to do; I didn’t spend much time online back in those days. Anyway. The early days were filled with a whirlwind of experimentation — colours, prints, every and all styles (I wore harem pants uninronically once, you guys). I was all over the place, in no small part because I was shopping mainly secondhand and fast fashion clearance racks (H&M in particular) and snatching up “bargains” indiscriminately.

2011 was the year of my first pregnancy. (Technically, I was only pregnant for about 6 months of that year. The balance of the year was lost to a postpartum haze, the less of which we speak, the better.) I totally wanted to be one of those cute, stylish pregnant women, and at the time I felt relatively good about my pregnancy style for the most part. In retrospect, I did OK — a little over-the-top with the colours and prints, but par for the course for my then-sartorial persona.

2012 was a tough year, style-wise. I struggled with my maternity style (and my maternity leave in general), and then I struggled with my back-to-work style too. I think that period coincided with my short-lived “must dress interestingly for the blog” phase, and the results were kinda, well, not great.

2013 was the year of pregnancy #2, when everything went downhill. I had a rougher go of it (although I was generally healthy, thankfully) and struggled with dressing my pregnant body far more than the first time around. To be honest, in retrospect, I hate pretty much all of the outfits I wore during that time. My goal at the time was to dress like my usual self, so I resisted maternity clothing for far longer than I should have; it was a strategy that had worked fine before, because of the way I carried my first pregnancy, but didn’t work so well the second time (I gained weight differently, and experienced far more water retention).

After I had my daughter, my body decided to surprise me and not do what I had expected it to do, based on my first go-round. The extra 20 pounds I was left with … well, they never really budged, even after I stopped breastfeeding. Since I didn’t have the time (or energy) to keep up with my previous fitness routine, that original 20 pounds slowly kept creeping up. Mentally, however, I was in a far better space than following the birth of my son, so I was able to devote some attention to figuring out how to dress my new body.

By that summer, I had hit a good groove. I even started wearing shorts for the first time! It was my first non-working (non-pregnant) summer in many years, and I really got into my casual clothes. Let’s just say, I spent a LOT of time at Old Navy and the J. Crew Factory stores in 2014 — enough to get on a first name basis with some of the sales associates. Good times.

Then it was time to get back to work (and a new role), which meant trying to figure out a whole new wardrobe. More shopping was involved — a lot of it on eBay. That fall was also when I started to get back into thrifting. Style-wise, I was still floundering a bit, but my first priority was feeling comfortable and confident in my own skin (and clothes).

In 2015, I feel like I started to really hit my stride. OK, not gonna lie: losing the extra 30 or so pounds I had been carrying for over a year and a half helped a lot. With a few notable exceptions, my body was more or less back to what it had been, pre-pregnancies. It’s a lot easier to dress a body whose proportions you know well, right? Plus, as one anonymous internet commenter once wrote in reference to yours truly (and I’m paraphrasing here), it’s not exactly a struggle to get dressed when you’re a skinny woman. She had a point, I guess. I’m fully cognizant that my sartorial “struggles” are of a very privileged kind — the result of having too many decent options, and an indecisive personality.

Getting back from that tangent, in 2015, I continued my refine my casual style — slowly moving closer towards what might ultimately be called a “colourful minimalist” aesthetic.

Due to a combination of weight loss and re-dedication to thrifting, there was a lot of turnover in my closet in 2015. Although I still did a fair bit of experimentation with my work clothes, I also began to narrow in on silhouettes and outfit formulas that made me feel most polished and confident.

Ah, 2016. At the risk of looking back on this and being embarrassed by unwarranted optimism, I will venture to say that 2016 has been the year of hitting my stride, style-wise. Not that there haven’t been missteps along the way, but I do think they are becoming more and more infrequent. I know, because it was really hard to pick just a few favourite outfits for purposes of this demonstration. So prepare for an onslaught!

First up, casual wear. I think I’ve finally nailed my off-work mommy uniform. My core colours are black, grey, white, blue, mustard, and khaki, and I’m happy to rock those every weekend.

My “fun” weekend wear is a looser category, with a less well defined colour palette and a more pronounced boho vibe. Thanks to thrifting, I’ve cycled through a lot of cute summer dresses, trying them on “for size” as it were, before settling on a smaller core of favourites. As I “recycle” all of my (already preloved) clothes — through donation, swapping, or selling — this has been a relatively inexpensive and guilt-free experiment. I highly recommend using thrifting as a way to engage in a similar process if you’re still trying to figure out your personal style, or if you simply like a lot of variety in your wardrobe game.

In 2016, I have also hit a stride with my work clothes. As I mentioned above, I think my current style can be best described as “colourful minimalist”. I’m happy with that, though I doubt it’s the end of the road, err, evolution.

But more than anything, I think it’s safe to say that 2016 has been the year of dresses. All the dresses. All of them.

Hope you enjoyed this visual trip back in time. I would love to hear your style evolution stories, so hit me up in the comments!