A Difficult Decision – Blue Collar Red Lipstick

That sounds rather ominous, doesn’t it? Well, don’t worry. I come bearing no bad news — but, as will become apparently shortly, neither am I bearing a clickbaity title. I really did have a difficult decision to make last month.

I had to choose one outfit to encapsulate everything I want the world to know about me.

Ok, maybe not everything about me. Just about my personal style and my beliefs in the beauty and value of secondhand objects. No biggie.

One of the people I’ve been fortunate to meet thanks to social media is the super talented Emilie Iggiotti. Emilie is more than just a great photographer; I have admired her dedication to making women feel seen by capturing their inner light and truest essence in portraits for years. We ended up connecting IRL thanks to our mutual love of all things thrift (which, honestly, is how I’ve met most of my friends at this point) and, to make a long story short, that’s how I ended up with a difficult decision on my hands. To celebrate our local thrift community, Emilie organized a “Portraits of Thrifters” shoot, generously offering each participant the opportunity to have a (complimentary) photo taken in their best secondhand duds. I couldn’t pass that up!

Since 99% of my wardrobe is secondhand, you would think that choosing an outfit for the shoot would be relatively easy; I mean, I could close my eyes and pull out any garment from my closet with almost complete certainty that it would be a preloved item. That wasn’t the difficulty. The difficulty was deciding on an outfit … that would best represent me to the world. Emilie has a fairly large audience on social media (larger than mine, anyway) and I figured there was a chance that my photo might end up being showcased, in some fashion, on her accounts. I had no issues with that, but knowing that it might be seen by (a lot of) others did make it more important to me to choose the right outfit.

After much deliberation, I narrowed it down to two different vibes:

To be clear, the decision wasn’t down to these specific outfits, only the aesthetic. The Eclectic Bohemian and the Ralph Lauren Woman. Why? It was a combination of things. I felt each of these aesthetics was representative of a facet of my personal style that I currently enjoy a great deal; any outfit in either of these vibes would make me feel like “me”, and I think that feeling comfortable and confident is one of the key elements of a good portrait. I also thought that these aesthetics would translate well on camera, and look fun and dynamic. Initially, I was also quite set on using the black Issey Miyake skirt on the right, because it’s one of my favourite thrifted pieces ever, but I eventually decided to focus on the mood of the outfit more than its elements.

I threw up a quick poll on Instagram to help me in deciding between the 2 options … and it was no help at all. Opinion was split almost exactly down the middle. I had no choice but to put my thinking cap back on. Someone had made the good point that a tulle skirt would bring lots of drama; personally, I was strongly leaning towards a black skirt (we’ll come back to why in a moment). Lucky, then, the fact that I had recently hunted down a black tulle skirt on Poshmark. It felt like a sign. I took the skirt out and started to improvise.

And when I tell that the ideas came pouring out … they really did. I ended up with three outfits I absolutely LOVED; I could have come up with more but had to stop because I knew my decision was about to get even more difficult, not easier. But I will say this: the freedom of this exercise — picking an outfit for a photoshoot where I could be as “over the top” as I wanted — proved incredibly creatively stimulating. I want to keep some of that energy for every day, tbh. And I wish that our society loosened up a bit and stopped policing fashion norms enough to allow everyone to feel that they can wear anything that makes them feel good and seen, any time, anywhere. Imagine if we never had to hear “where are you going to wear that” ever again? That would be so nice.

Anyway, back to my difficult choice. Here’s the first outfit I put together — a mash-up of the Historian and the Bohemian:

The main downside of this choice was wearing a wool blazer at the end of June. Can you say overheating?

This next outfit was a total tangent, but I fell in love with it anyway:

I just love the offbeat drama of it. I saw it almost as a palimpsest of my personal style, past overlaid with present. I feel like I need to find some gallery opening or avant-garde theatre show where I can wear this for real.

The last outfit is the one I had at the back of my mind from the beginning:

I think you can see, here, why it had to be a black skirt. This striped top drives this entire outfit — the black, red, and white palette was needed to make it come alive. This also gave me the chance to wear some of my favourite secondhand accessories, including the cowboy boots and the bolo tie.

So, what do you think: which outfit did I end up wearing for my photoshoot?