Details: Wilfred sweater (thrifted), J. Crew shirt (secondhand), Laura Ashley skirt (thrifted), Mia shoes (retail)

Thoughts: I have been looking for Laura Ashley at the thrifts for a while, and I finally found this skirt, which is VERY Laura Ashley so I am quite pleased. It’s more of a summer piece, for sure, but I think I can make it work during this still-transitional phase of fall. We have been very lucky this year to have a proper fall season, stretching well into October. I feel especially lucky because I adore fall as a sartorial season and it’s usually so short. I really loved wearing this outfit – it’s my fave kind of layering because it’s easy but has visual interest built in, feels casual but looks intentional – and it’s a nice blend of my summer and fall aesthetics.

Details: Toni T dickie (thrifted), Lord & Taylor sweater (thrifted), Etro skirt (thrifted), Nanette Lepore blazer (thrifted), Mia shoes (retail)

Thoughts: Continuing my exploration of mini skirts, this was a pretty good effort. This lemon yellow is a colour I haven’t worn much, and it wasn’t an obvious choice for this outfit, but I actually love the contrast it brings to the ensemble while also lightening up the colour palette. The pattern of the jacket is actually chartreuse and purple, so there is subtle funkiness going on.

Details: Eddie Bauer sweater (secondhand), Tommy Hilfiger jeans (thrifted), Mia shoes (retail)

Thoughts: Are you sensing a theme yet? I have been wearing this platform loafers non-stop lately. Honestly, they go with everything I want to wear right now, to the point that I have to stop myself from reaching for them every single day. Patting myself on the back for making my one retail purchase of the year really count. I am also very pleased with these jeans. I think they are from the mid-2000s, but the kick flare silhouette feels fresh again to me. I’ve been wearing these a lot in lieu of the bootcut pair I also thrifted. I think it’s because these jeans work so well with my platform loafers, and the bootcut will work better with ankle boots which I haven’t started wearing yet. I may need to re-think this because once it starts raining (or, worse yet, snowing), full-length jeans might become a trickier proposition. Wet hems are the worst.

Details: J. Crew shirt (secondhand), Tse sweater (thrifted), Paul Smith pants (Poshmark), J. Crew shoes (retail)

Thoughts: I picked up these pants on a bit of a whim. I have been wanting a pair of plaid pants for a while, and was looking for a more relaxed silhouette (not cigarette/skinny pants); these pants seemed to fit the bill but I had some reservations. The listing photos didn’t show the pants very well, which made it difficult to know what the silhouette would look like on an actual person. I also had concerns about the sizing, as the pants are made in Italy; Italian sizes are quite different but I didn’t know whether the pants followed that sizing or not. I sat on the listing for weeks and then, randomly, the seller dropped the price to $20. Did I mention that they are wool and worth $$$? I did some Googling and was able to find an old stock photo that showed the pants worn by a model, which at least gave me a better idea of the silhouette … so I took a risk. And you know what? It was worth it. They fit great and look fab. This was a pretty plain outfit but I am excited to try for something a little more edgy next time.

Details: Marni top (Poshmark), Thierschmidt skirt (thrifted), butterfly necklace (secondhand), Stuart Weitzman shoes (thrifted)

Thoughts: Not much to say about this outfit other than that I enjoy these pieces and am always happy to wear them.

Details: Uniqlo top (thrifted), Vero Moda pants (thrifted), J. Crew blazer, belt and shoes (all retail), Stella & Dot necklace (thrifted)

Thoughts: It’s been years since I wore this blazer — it was one of my first upcycle/embroidery projects back in the day. I decided to pull it out and create an outfit around it. I came up with the colour palette on the fly, but I think it works. It’s all muted shades, which helps make it feel cohesive, I think.

Details: Della Spiga jacket (thrifted), Esprit belt (thrifted), Ralph Lauren skirt (thrifted), Ferragamo shoes (thrifted)

Thoughts: You know how I did Romantic Prairie this summer? This is Romantic Highlands. Same but different.

A question I get asked with some frequency on IG concerns my Poshmark strategies; not to toot my own horn, but I have been able to score some pretty sweet deals from time to time, and I guess people want to know the secret sauce.

There is no secret sauce.

Wait, don’t X your way out of here just yet. I have some thoughts. Let’s talk about it.

I’ve been on Poshmark for 2 years and during that time I’ve bought … ahem, one or two things. I’ll spare my blushes and not attempt to give you an exact number. I could write a lot about my experiences on Poshmark — trends I see, things that bug me, weird seller behaviour — but anecdotes are probably not going to help you much. Overall, I would say 95% of my experiences have been positive, in the sense that I received what I was expecting from the purchase. I’ve only ever done one return, when the seller sent me the entirely wrong item and Poshmark reimbursed me, and have had a couple of situations where the item came with flaws not disclosed in the original listing (but not major enough for me to open a case with Poshmark). That’s not to say that all my purchases were hits, but generally where they have fallen short, it’s because they were impulse buys I didn’t think through well enough.

One thing that may have an impact on my Poshmark experience and the searching strategies that I’ve found useful is something I haven’t specifically called out before. Maybe it’s obvious, maybe not. I shop on Poshmark Canada. Based on limited exposure to the US version of the app, my sense is that Poshmark Canada remains rrelatively smaller (i.e. with fewer listings overall). You will see in a moment why this could be important.

I have discussed my general strategies before but let’s do a more in-depth refresher. As time goes on and the app itself evolves, my strategies get tweaked. Gotta stay nimble!

One strategy is searching up specific brand names — e.g. “Dries Van Noten” or “MaxMara” — and sorting the results one of 2 ways depending on what I’m looking for:

• Sort by “Just in” if I quickly want to see new listings (posted since my last check). Remember how I said that Poshmark Canada is a smaller market? That makes it feasible to browse the results of a general search for most high-end designer brands within a relatively short time because there won’t be more than a dozen new listings* if I run the search on, say, a weekly basis. [*Note: this is true for most clothing-focused high end brands. For brands that also sell accessories, like Gucci for example, you will end up with a lot more new listings.]
• Sort by “Price – Lowest to highest” if I am in the mood to see what bargains popped up recently that I might have missed. I use this less frequently, usually if I’m bored. I don’t usually recommend letting price be the main driver of your clothing purchase decisions, but sometimes a price cut will bring an item previously out of budget within reach. Or make me more willing to consider a “style risk” type of piece.

This approach has its limitations — the more popular the brand, the more results to browse — but the advantage is that, through a general search, you can come across cool pieces that you didn’t already know about. Otherwise, if you are looking for something specific (either a particular item or a general category of items), it’s better to combine the brand name with a descriptor (for example “dries van noten skirt”) or to narrow the search down by category (“dries van noten” then select “skirts” under category).

I never select the Poshmark brand name category to run my searches, and instead use the name itself as a search term. I don’t know why, but I find that using Poshmark’s brand category (if it exists) sometimes doesn’t catch all listings. I don’t understand their algorithm. If the brand name is distinctive enough, I often use a shorter version — like “cornejo” instead of “Zero+Maria Cornejo”. I have no idea if this is the optimal approach, but it’s what works for me.

Also! Poshmark now has a Saved Searches feature (finally!) so you can save your most frequent searches and re-run them without having to type out the terms every time. It also helps you remember all the things you want to keep an eye on.

The other strategy is using descriptive search terms. These might be one word only — in my case, “turquoise” has been a long-standing search — or something more detailed. For common brands like Zara, I may combine the brand name and a descriptive term. Depending on what I am looking for, that could be something generic (“Zara jeans”) or something specific (“Zara sequin skirt”) or something SUPER specific (“Zara blue sequin skirt”). Obviously, the more generic the descriptive term(s), the more results you will get. I don’t always have time for mindless browsing but sometimes I’m in the mood — browsing a general category is how you can come across unexpected gems. Again, you can sort by “Just in” or “Price – Lowest to highest” depending on what you want to see first.

If I am using one generic search term — like “turquoise” – I will sometimes narrow the results by category — in my case, Jewelry. I call this a “wild card” search because you never know what you might get. I’ve found quite a few amazing pieces this way, and discovered new-to-me designers.

There is something of an art to choosing search terms and I couldn’t possibly cover it all in one post that is already getting too long. The more specific the terms, the narrower the results. If your search isn’t turning up enough results, widen it — use fewer terms or different (analogous or related) terms. Here is an example from my current search list. I mentioned before that I am looking for palazzo-style jeans and I have a number of on-going searches saved in Poshmark for this purpose. My search terms include:

• “palazzo jeans” (obvious)
• “trouser jeans” (in my opinion, not as accurate of a descriptor but one used by many brands and I want to see any adjacent styles that might meet my needs)
• “wide leg jeans” (this is very broad and I often combine it with a brand name like Zara — why Zara? because it’s a trend-based brand so they are likely to have a version of most popular current trends.)

To be able to run effective searches, synonyms are your friends. People describe items in different ways, not always using the precise industry term. For example: “bustier” and “corset top” and “crop top” — these are technically different things, but I have seen them used by sellers to describe very similar items of clothing.

An important drawback to using very specific search terms is that it may miss relevant listings where the seller doesn’t include any descriptor terms. This is especially true for non-resellers, i.e. people selling from their own closet. People who don’t have experience selling online will often not include relevant information; some might just list the brand and size but no other description. This means that, even if the item meets the criteria of your search, it won’t show up in the results. There is no surefire way around this other than to run very, very broad searches and browse a LOT. I’m not usually in the mood for this, but if I have time to waste, it’s an approach that can pay off. Non-professional sellers often offer better prices than resellers.

The general moral of the story: success on Poshmark is not entirely unlike success at thrifting. Checking the app regularly increases your chances of finding cool bargains. The more time you spend browsing, the better your chances. Sometimes, it’s luck of the draw – being in the right place at the right time (when a listing goes up).

I have a whole other set of strategies I use once I’ve identified a listing of interest … but let me know if that’s something you would want to read more about.

Details: vintage (no label) dress (thrifted), Zara blazer (thrifted), Wilfred sweater (retail), Ferragamo shoes (thrifted)

Thoughts: I’ve been saving this dress since the spring, planning to use it to replicate some Ralph Lauren romantic-prep outfits. I wanted something frothy and floral; initially I was looking for a black floral chiffon maxi skirt (or dress) similar to my original inspo, but this brown handkerchief hem dress hits the spot. Plus, I am a bit obsessed with brown this fall. Never thought I would say that but here we are. Head to toe in brown. Who am I, even?

Details: Gap sweater, Toni T dickie, Nanette Lepore jacket, Studio Lysa skirt (all thrifted), Manolo Blahnik shoes (eBay)

Thoughts: Never fear, I still do colour. I randomly hit on this sweater-jacket combination and I am obsessed. The jacket is a chartreuse-purple houndstooth, though the colours don’t photograph as vivid as they are in real life. I love how well this pattern pairs with this particular stripe sweater. I have a few (all from Gap) and I can tell you — not all are equal when it comes to this particular combo. I added the skirt to bookend the stripes, and it think that really works too. It’s academichic with a colourful twist.

Details: Gai Mattiolo jacket (Poshmark), Toni T dickie, Pilcro sweater, Inc International pants (all thrifted)

Thoughts: Speaking of colour … here’s something to really wake up your eyeballs. It’s fun. I love the flower pin — it reminds me of SATC’s Carrie.

Details: Club Monaco sweater (retail), Della Spiga jacket, Josef belt, BDG pants, Chelsea Crew shoes (all thrifted)

Thoughts: As much as I’m loving brown right now, I have to say that green-blue combinations are a forever favourite. There is something so lush but also soothing to this pairing. But look: still managed to sneak in some brown too.

Details: Toni T dickie, Everlane sweater, Ralph skirt, Gap jacket (all thrifted), Mia shoes (retail)

Thoughts: Same basic outfit as last week, but changed up the shoes and topper. I like this version too. It’s rare that I repeat outfits this literally, but I couldn’t resist. The brown-black combo in the shoes has inspired me to extend that palette to the rest of my outfits.

Details: J. Crew sweater and shirt, Urban Outfitters pants, Mia shoes

Thoughts: An old sweater that still brings me joy, plus some new(ish) pants that are just so easy to wear. Sometimes, simple outfits are just the ticket.