Another thing I get asked from time to time on IG is how I translate style inspiration into real-life outfits. In recent years, my approach to outfit-making is much more intuitive than process-driven, so I am not sure if I am the right person to talk about this topic. If you are looking for detailed analysis, Margaret of @mgetsdressed is really good at talking about her process and breaking down style inspo. But I am going to take a stab at this topic and hope that it’s at least middling useful.

The first thing I do when I see a photo that lights up my lizard brain (to borrow a phrase from another IG users, Frisky Gatos), is ask myself: why do I like this? Very often, it’s because the outfit elicits a certain mood, feeling, mental image, whatever you want to call it. Other times, it might be a colour palette, or a particular silhouette. If it’s something specific like that, recreating it in my own outfits is pretty straightforward. If it’s colour palette, I look for pieces in my closet that are the right colours (or close enough) and play around until I find a combination of items that works together and approximates the inspiration palette. If it’s a silhouette, same thing: I look for pieces that have similar proportions (irrespective of whether the colours or other details are the same or not) and then figure out if the versions I have actually go together or not. Sometimes, this means I end up with really interesting pattern or colour combinations that I might not have otherwise thought to create. Bonus!

The more complicated — and, to me, interesting — process is when I am drawn to an inspiration photo in its totality … in other words, because it embodies a mood or idea that captures my imagination. This doesn’t mean that my goal becomes recreating the exact outfit. Sometimes that is feasible, but more often than not it isn’t, because I don’t have pieces that are exactly the same or even close. Moreover, I am personally not a fan of copying outfits. Style is a form of personal expression to me so even if I am inspired by someone else’s ideas, I feel the need to put my own creative spin on them. Plus, if you use inspiration as a guideline rather than a prescription, you can create more than one outfit that shares the same DNA. I am a huge fan of remixing (i.e. wearing your clothing in different ways) — it staves off “closet fatigue” or “style ruts”.

Okay, so you like the vibe of an inspiration outfit … now what? The next thing I do is try to break down the key elements of the outfit, and then decide which ones are critical to that vibe. It’s hard to talk about this in the abstract, so let’s use a visual example. I have had this Ralph Lauren runway outfit saved since last spring, and I go back to it regularly.

Here is what I like about it: it has a very Romantic feel but it’s an outdoorsy, not-too-frilly vibe. There is an autumnal coziness. I love the juxtaposition of the floaty skirt and the rougher jacket — that feels important somehow.

I won’t lie: I have been looking to find a skirt just like the one in the inspo photo for months now. Not simply to copy this outfit (see above) but because I think it would fit into my wardrobe really well. I haven’t found a “dupe” yet, but I did end up buying some items that have a similar vibe — floral, floaty, maxi length.

My breakdown of the key elements is as follows:

• semi-sheer floaty (chiffon) patterned (preferably floral) maxi skirt (or dress)
• heavier weight jacket, preferably with texture
• high neck knit top (different texture than the jacket)
• belt

Looking at the inspo photo more closely recently, I realized that there is actually a vest over a turtleneck (I think). That opens up a few more possibilities, but I actually don’t think that the vest is a key element; I think the main thing is having texture in play through the jacket and top.

Here was my first attempt:

The only thing I didn’t love about this outfit was that the dress wasn’t quite long enough. The proportions with that long blazer are just a bit off. If the dress came to my ankles, it would have been perfect. To me, the shorter length detracts from the Romantic-ness of the overall vibe. It feels less lush.

Here is a very different take:

The colour palette is totally different, right? But, to me, the mood is the same. A minor nitpicky observation: the material of the dress is heavier, and the cut of it a little narrower than I would have liked, but the handkerchief hem compensates by creating that “floaty” feeling. The shorter length of the jacket here balances the (still) too short length of the dress. I didn’t feel this outfit needed a belt, so I didn’t add one.

One more:

Here, I went back to a more literal translation with the top half, but tried a more out-of-the-box option for the bottom half. This skirt has a busier pattern (it’s actually a mix of patterns) which has the disadvantage that it could pull too much attention and overwhelm the outfit. The tiers create visual weight (not good) but also a certain lushness (good). The length works well with this longer and oversized jacket. I really like the juxtaposition of the velvet waistcoat and the corduroy jacket. Overall, I think it really works.

And this is how I got 3 outfits (and more to come, I’m sure) from one inspiration photo:

I hope this breakdown helps to illustrate my process — which, honestly, until now I have not put into words in my own head — and gives you some ideas about how to approach the inspiration-to-real-life transition. Happy experimenting!

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.