Details: COS sweater, H&M Studio skirt (both thrifted), Zara boots (retail)

Thoughts: I decided to pair these 2 pieces because the patterns struck me as sort of similar, with the through-line of orange as a cohesive element. I think it was a successful experiment! I’m glad I went with an outside-the-box pairing, since my default for this skirt would be black and white pieces. I am still figuring out if the skirt is a “forever” piece for my closet, but I am enjoying what it brings to the table at this moment.

Details: Tabi sweater, Ralph Lauren skirt, Fluevog shoes (all thrifted)

Thoughts: I loved this outfit even more than I thought I would, and I knew it would be a good one because I love both of these pieces a lot — separately and, evidently, also together. There is something about pairings of contrasting black-and-white patterns that feels very satisfying to me right now. And, of course, floral and plaid is always a winning pattern mix.

Details: Joie sweater, Tommy Hilfiger jeans, Office London boots (all secondhand), Amaryllis coat (retail)

Thoughts: Winter casual at its best. This sweater continues to disappoint quality-wise (it is already pilling) but it is so fun to wear. As you know, I find colours to be mood-enhancing, especially on cold, grey winter days. The other elements of this outfit are all unqualified successes, though. We know this coat; it’s 6 (7?) years old and still going strong. The jeans are my new go-to — the kick flare is perfect with winter boots. Speaking of which, this Office London pair was a great find. They have a nice, grippy bottom (a mini lug sole) and walkable heel which makes them perfect for errands and outings that don’t involve a ton of outdoor trudging in snow (they don’t have enough insulation for that, though wearing them with a thick pair of socks makes them quite toasty).

Details: H&M dress, BCBG belt (both secondhand), Zara boots (retail)

Thoughts: If you’ve been around for a long time, you know how much I love a “potato sack” dress. They’re so fabulous! And comfortable! And easy to wear casual — full potato mode — or dressed up (half potato? lol). Case in point: add a belt (or harness!) and voila! The bold graphic print of this dress really appealed to me as well, and I think the colour palette offers interesting remixing options from my wardrobe. Picture this with a lavender sweater …

Details: Le Lis top, Holding Horses tunic, Topshop pants, Stuart Weitzman shoes (all thrifted), selfmade necklace

Thoughts: I love this colour palette of muted blues and terracotta brown. I also like the mix of plaid and windowpane patterns — both geometric but different.

Details: Eddie Bauer sweater, H&M dress, Mexx skirt, Geox boots (all thrifted)

Thoughts: I looooooooved wearing this outfit. It was shockingly warm too (I wore a coat over it). Layering the Mexx skirt under the tulle dress — and over some fleece leggings — kept my legs nice and toasty. I also had 3 layers on the top, but the one that really matters is this vintage Eddie Bauer sweater that I adore. This outfit was inspired by a 1980s Ralph Lauren look (what else) and has that Jo March-on-the-prairie vibe that I’ve been loving this year.

Details: Babaton turtleneck, Tommy Hilfiger cardigan, Denim & Supply jacket, H&M pants, Brave belt, Eileen Fisher shoes (all thrifted)

Thoughts: Once again, bringing the prairie/southwestern vibe into the winter season with some judicious layering. What I liked there was the different textures and contrasts — black cotton turtleneck, white chunky knit, patterned jacket. It gives depth and intentionality (is that a word??) to the outfit.

Details: Equipment shirt, Lord & Taylor sweater, Etro skirt, LAMB coat, Office London boots (all thrifted)

Thoughts: I took advantage of some warmer weather to wear one of my lighter winter coats, this fabulous plaid number. I used some of the colours in that pattern — yellow and olive, to be precise — to guide the rest of my outfit-building. It was a bit of a cheat, as I wore this sweater/skirt combo before, but it worked so well in this iteration too.

Today, I want to pull away from my usual topics and talk meta.

I started this blog in 2010, during the early-ish heydays of personal style blogging. Monetization was only just beginning to gain momentum, and sponsored posts were still a relative rarity. Almost from the beginning, I realized that blogging would not be a path to fame or fortune for me. As a former teenage wallflower, popularity was a tempting prospect, but it quickly became apparent that I did not have the temperament to pursue it in any meaningful way. Chalk it up to my internal push-and-pull of wanting to please people but also keep them at arm’s length and “do my own thing”. I am also not a natural salesperson; goodbye, sweet sponsorship money! I always feel responsible when people act on my recommendations – which is unreasonable but it is what it is – and I knew that adding financial incentives into the mix would only exacerbate that sense of responsibility. I don’t want to feel guilty if you buy a skirt and you end up hating it! So making the choice not to monetize – either through sponsorships or affiliate linking – was relatively easy. It is also worth mentioning that I was fortunate to have a day job that provided financial security, so I did not face other pressures or inducements to monetize in that fashion.

In the intervening years, the landscape of social media has changed tremendously. Blogging started to decline, and influencers were born. Side hustle culture became mainstream. While it seems like there is fatigue with traditional influencer monetization – i.e. sponsored ads and the like – monetization isn’t going anywhere.

I have never regretted not taking advantage of the sponsorship and blog monetization opportunities I’ve been offered over the years (or not trying to pursue others). My feelings about being a salesperson haven’t changed. I gave up chasing social media popularity entirely by making my main Instagram account private. To be perfectly honest, I thought I was “outside of it all” – immune to the lure of monetization, so to speak.  

Turns out, maybe I wasn’t.

Because while I didn’t monetize this space or my fashion blogging social media presence, I did monetize other parts of my life. I sell my art, even though I cannot price it in a manner that is truly reflective of the effort and skill that goes into it. I’ve talked about this before, but a big reason for that was the need to “legitimize” my art. I also, for a time, monetized my thrifting hobby by offering personal shopping packages. Why? Probably because I internalized that ubiquitous message that turning hobbies into side hustles is The Very Best Idea Ever. I was recently listening to an episode of the podcast Money Feels, in which the co-hosts (Bridget Casey and Alyssa Davies) made a very thought-provoking point: the push towards side hustles is a symptom of the financial insecurity which our capitalist system instills in people. That insecurity is very real for many people — caught up in the gig economy, low wage work, crippling student or medical debt, and so on — but it can also be a state of mind. The constant preoccupation with accumulation lest one fall behind or run out. In a way, this fear isn’t entirely unfounded either; most of us are a series of unfortunate incidents away from financial crisis in a society where social safety nets are shrinking by the day. [You know how it’s said that some people act like they are “temporarily impoverished millionaires”? It might be better if we all acted (and voted!) like “temporarily well-off paupers”. But now I am really digressing.]

In my case, while I am not suffering actual financial instability, I am still, clearly, prey to the scarcity mindset. Nowadays, I am trying to be more alert to that and its impacts on my decision-making — not only in relation to monetization of hobbies, but in general. As for my personal thrift shopping services? I stopped those a few years ago; the work stopped being fun and started being a source of stress almost as soon as I monetized it. I am also re-evaluating my feelings around being a “legitimate” artist and the role of monetization in my experience as an artist, but that remains a work in progress.

There is one thing which has brought this all back onto my front burner recently. Everywhere I turn these days, it seems like people are offering Patreons, subscriptions, Substack newsletters. They are not selling material things, or at least, that isn’t the primary draw (some may still use affiliate links in their paid content). They are selling content or, depending on how you look at it, creative product — not different from a song, or a piece of art. I am not going to lie, there is an appeal in this for me. Why? I guess at least part of the appeal goes back to that idea of legitimacy; if someone is willing to pay for it, your content must be worthy. However, put another way: if someone is reading your content, it must be worth something, no?

I keep coming back to this question. Is my content worth something? If I am writing because I enjoy it, does that negate the significance of being paid for it? Does reaching a (presumably) wider audience compensate for the lack of other recompense? Where content is personal in nature — opinion writing, if you will — does monetization mean selling access? How do I feel about that? Over the years, my writing has enabled me to connect with and develop friendships with people whom I would not otherwise have met; how does one bring money into something like that? At the same time, the majority of people who consume my content do so anonymously and without any reciprocity which, at times, I have to admit, does sting a little.

This is where I have to tell you that I don’t have a neat conclusion to this post. All I know is that I keep seeing new subscription notices — not the first and not the last tool of its kind, for monetization is a many-headed Hydra in our world — and wondering where I fit into this paradigm. Maybe this is just another facet (head?) of the monetization culture that I need to come to grips with. If anything, I’ve realized that there isn’t a “one answer fits all” solution to the questions posed by monetization culture. And this isn’t a long-winded way of telling you that I’m putting the blog behind a paywall, by the way. But if there is a takeaway, it’s that monetization as an extension of capitalist ideology is pervasive and tends to sneak into all corners of life where you might least expect it, and calls for constant (re)examination.

I would love to hear your thoughts, whether as content creator, content consumer, both, or just as a person living through these late stage capitalism end times. Have you grappled with the question “to monetize or not to monetize”? Have you jumped all in, or opted all out, or found some kind of balance (and if so, definitely share the secret sauce!)?

Details: St. John top, Nanette Lepore jacket (both thrifted), Babaton skirt (Poshmark)

Thoughts: I still love this St. John top so much – I adore the boldness of the trompe l’oeil chain design. It’s a thin knit (which St. John does so well) so it has a nice weight to it without being too heavy/thick. This blazer has been something of a revelation; in some ways, it’s pretty traditional — what, in my mind, I call an “office blazer” — so something I have not been gravitating towards lately, but for some reason, this has been such an outfit-maker for me lately. I think it’s the pattern and the colours (purple and chartreuse though they don’t photograph clearly as such), which make it unexpectedly funky.

Details Club Monaco turtleneck (retail), Ralph Lauren tank top, Zara blazer, H&M pants, Brave belt (all thrifted), Louise et Cie shoes (retail)

Thoughts: This is a pretty standard Historian outfit formula, and I don’t have much else to add — it works for me every time. I’m thrilled to have found this vintage RL knit tank top because, under a blazer, it looks just like the sweater vests that I have been coveting for months.

Details: Polo Ralph Lauren dress (gifted), Zara top, Holding Horses tunic worn open, Nine West shoes (all thrifted), selfmade necklace

Thoughts: A friend of mine gifted me this RL dress because she knows how much I love the brand. I had been waiting for the right outfit inspiration and feeling a bit stumped until I thrifted this plaid tunic. The colours and contrasting plaid seemed like a fortuitous combination, and so they are. This was such an easy, comfortable (but still fun!) outfit for WFH for a day when I didn’t feel like “dressing up”.

Details: Oak & Fort shirt, Ralph Lauren skirt (both thrifted), Gap vest (Poshmark), Zara shoes (retail), Warren Steven Scott earrings

Thoughts: In contrast, here is a “dressed up” version of my WFH outfit. Effort-wise (and comfort-wise), it’s not really any different, but it feels dressed up to me. I couldn’t resist this vest: patchwork plaid? Yes, please. Since one of the patches is Blackwatch plaid, I had to try it with my favourite RL skirt. Am I an honorary Scot yet? 😉

Details: Wilfred shirt, Everlane sweater, Gap skirt, Avec Les Filles jacket, Office London shoes (all thrifted), Warren Steven Scott earrings

Thoughts: I’m sure you can see why I picked up this skirt — the colours and pattern, of course. Luckily, I am still in my “mini skirt experimentation” phase and, also luckily, it’s going well. I think I’ve found the key (for me) to mini skirt outfits: tights. They don’t have to be black (although black works well here) as long as they are opaque. I just don’t like the bare leg look on me — the proportions look wrong in my eyes, as if the vertical line is being chopped up at the wrong place(s). Somehow, opaque tights solve that problem!

Details: Suncoo blouse, no label cardigan, Jenni Max skirt (all thrifted), Rafael Alfandary necklace (consignment), J. Crew shoes (retail)

Thoughts: There is a flavour of Edwardian schoolteacher to this outfit, and I’m not mad about it. We can call it academichic of another era, right? I love the colour of this velvet skirt; it’s a sort of mousey greige with silvery highlights — very unusual and cool. I do wish there wasn’t a zipper in the front, as it adds bulk where none is required; if it weren’t for that, I think I would wear this skirt a lot more often.