Details: Anthropologie dress, Lena Bernard necklace, Coach bag, Brixton hat, cowboy boots (all secondhand)

Thoughts: A simple outfit — you can’t get more simple than this — that is ALL about the accessories. I didn’t know how much I needed a black felt hat in my life until I thrifted this one. I was surprised by how wearable it is even on a warm day, which is great because it offers a nice alternative to my straw Panama hat. I like having different options to suit different aesthetics, and this one works better with the SW/prairie side of my closet compared with my other option. I am also surprised by how much I love this short dress/cowboy boot combo. Now that I have acquired a pair of (black) bike shorts, making it a proposition fraught with a lot less risk (of flashing), I see a lot of appeal in it. Too bad I only have 2 short summer dresses in my closet. Just imagine a flirty, swirly eyelet number! Something to think about, anyway. In the meantime, this dress never not gives 110%.

Details: Reitmans top, Lira jacket, vintage skirt, Dooney bag, Chie Mihara shoes (all secondhand)

Thoughts: I found this patchwork skirt at a garage sale, which is noteworthy insofar as (a) it’s fab! and (b) I never find clothes at garage sales! It is a teeny bit sheer, which is fine because — remember my bike shorts? Yeah, that was a good thrift purchase too. They’re another staple I never knew I needed and now can’t live without. Sometimes, it’s “boring” pieces like it that can make the biggest impact on your wardrobe, by unlocking the potential of other items or combinations. I might add this striped tank top to that list. I have a love-hate relationship with stripes; they’re so versatile — this top will go with so many things in my closet — but if they’re the wrong type, they make me sick. Literally. Thin stripes spaced too close together make me dizzy. This version? Works great.

Details: Tommy Hilfiger shirt, Fossil belt, H&M pants, Coach bag, Ferragamo shoes (all secondhand)

Thoughts: Vertical stripes, on the other hand, I can wear all day long. I love this men’s shirt so much; the navy, red, white and yellow combo is eye-catching but classic. This was a super basic outfit that punched above its effort level.

Details: Ralph Lauren shirt, Dries Van Noten skirt, tulle skirt, vintage belt, J. Crew shoes (all secondhand)

Thoughts: Speaking of stripes, this was my homage to Dries Van Noten upon news of his retirement from his eponymous label. As many of you know, DVN has been an inspiration to me for many years, and I treasure the pieces I own — including this skirt, which a dear friend gifted me years ago. It’s knee-length, which isn’t a style I enjoy wearing as much these days, but it’s too fabulous and precious for me to ever part with it. To make it fit the me of now, I layered it over my blue tulle skirt; the colours work together perfectly, and the skirts are compatible, size-wise as well. The DVN is loose enough to accommodate the extra layer, and the tulle skirt is not so voluminous as to be impossible to accommodate. Call it kismet.

Details: Zara dress, Jessie vest, Elizabeth & James vest, Manolo Blahnik shoes

Thoughts: Double the vest, double the fun? I would say so, wouldn’t you agree?

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?

Details: Tahari blazer, Chicwish skirt, Le Chateau belt, Stuart Weitzman shoes (all secondhand)

Thoughts: I have been hunting for a black tulle skirt for a while. A specific black tulle skirt. This black tulle skirt. I have the same style in blush pink and love the design; for being fast fashion, the quality is decent. I wanted a dark coloured version (either black or dark grey) to complement the dark academia/goth side of my aesthetic. By lucky coincidence, around the same time that I finally snagged the skirt on Poshmark, I came across this vintage blazer at the thrifts, and I immediately knew that I needed to make this outfit happen. The cut of the blazer gives me Dior vibes with its beautifully tailored waist, so I knew it would be perfect for recreating a certain ad campaign, featuring Jennifer Lawrence, that has been living rent-free in my head for the last 5 or 6 years. I added a belt to emphasize the silhouette, but kept the rest of the outfit very simple. Maybe next time, I’ll try it with a tie.

Details: Ralph Lauren shirt, Pilcro sweater, Mexx skirt, Fossil belt, Chloe shoes, Tignanello bag (all secondhand)

Thoughts: I finally did it. I went full preppie. And I felt glorious in this outfit. For a few brief hours, I had the confidence of a woman named Muffy or Bunny, considered taking up tennis, and pondered what I might name the family’s hypothetical golden retriever. But then I came back down to earth, and decided to forego the tennis (my knees wouldn’t allow it) and the dog (ditto my husband’s allergies) and re-read True Prep instead. All joking aside, there is a lot to be said for this outfit. I wasn’t kidding when I told you that I felt great in it; it’s a perfect choice for a warm spring day — casual-but-polished, comfortable, breezy. It would look nice as a simple 2-piece outfit, but the sweater takes it into chic territory by adding a pop of contrasting colour (without overwhelming the light colour scheme) and a bit of texture. I am now a devoted fan of the sweater-tied-around-the-shoulders as an accessory. Think of it as a heavier scarf. Love!

Details: Ardene top (retail), Prairie Trail Goods cardigan (swap), Ralph Lauren skirt (eBay), vintage belt, vintage cowboy boots (both thrifted), MbMJ bag (swap)

Thoughts: I stole this entire outfit from my friend Josh of Prairie Trail Goods — parts of it, literally. Well, ok: maybe not stole, exactly. She did willingly swap the cardigan. I’m pretty sure she wore it to my clothing swap last year, which is probably when I fell in love with it, and she wore it with this skirt. Well, ok: not this exact skirt. But one just like it … which I proceeded to hunt down on eBay. And now look at me! I look almost as fabulous as she did. Who needs fashion magazines for inspo when you have stylish friends.

Details: Tahari shirt (thrifted), Pendleton blazer, Ralph Lauren belt (both Poshmark), Banana Republic jeans (retail), Coach bag (secondhand)

Thoughts: This might well have been my first proper attempt at a Canadian tuxedo lewk. Denim-on-denim always felt like too much denim for me in the past … and then I saw some menswear inspo on IG — pairing double denim with a wool blazer — and suddenly had to give it a try. Most of my plaid and check wool blazers are in storage at the moment, but I had this lighter-weight Pendleton one at hand, so I gave it a whirl, and you know what? I loved it. Planning to try a few more combinations before summer’s over … and then a few more come fall.

Details: Ungaro dress, vintage belt (both thrifted), Prairie Trail Goods vest

Thoughts: I don’t typically like to wear a lot of beige because the colour doesn’t do much for my complexion or my soul, but I will never part with this vintage Ungario wrap dress. The quality is so phenomenal, it would be a crime to do so. Some day, my daughter may appreciate it (and, as a brunette, will probably look smashing in it). The fabric is a heavy linen with a heavenly drape, and it falls so nicely — hugging the body without feeling suffocating in the summer. And I will say this for beige: it does make a nice canvas for statement pieces, like this beautiful vest made from upcycled quilt pieces by my super talented friend.

Details: Guess bodysuit, Zara blazer, American Eagle jeans, Mexx belt, Aldo shoes (all thrifted)

Thoughts: This Guess logo brings back a lot of memories from my 90s adolescence, which is why I ended up thrifting this bodysuit. At least I think it’s a bodysuit; it might also be a swimsuit (albeit one lacking any form of boob support whatsoever). The back is completely cut-out, which makes a topper a necessity for me. Luckily, this Zara blazer is a great match. I paired the combo with the American Eagle jeans I had thrifted for my daughter, who rejected them for reasons lost in teen-parent translation; I was originally going to exchange them, but then I tried them on and decided they were worth a little experimentation. They are not as wide leg as most of my other recently acquired denim, but they are also not straight-leg either. To me, they are, for lack of a better descriptor, very Gen Z coded … which intrigued me, not because I have any desire to chase the approval of the “youths”, but because it represents a step outside of my comfort zone as far as jean silhouettes go. There is a fine line between trying to “look younger” and trying out new styling ideas, and I think I managed to walk it with this outfit. All the while incorporating a bit of nostalgia.