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.

Details: Ralph Lauren turtleneck, Michael Kors skirt (both thrifted), Stella & Dot necklace (Poshmark), Zara shoes (retail)

Thoughts: I loved this outfit so much. This skirt makes for an even better dress! The waistband is elastic, so it can comfortably stretch to wear as a strapless dress. And it’s super comfortable! The turtleneck doesn’t look exciting in this context, but it was a great recent thrift find. Turtlenecks are a staple for me in the colder seasons — I use them as a base layer most days. I have a few versions. The Club Monaco ones you’ve see me wear a lot are a wool/viscose blend that is very lighweight and non-scratchy — this is key for anything that I wear next to my skin. I also have a couple of cotton blend black turtlenecks that can also be worn next to skin, although they are less warm than the wool blend ones (which makes them better for some outfits, depending on what I am layering on top). I then have a couple of cashmere ones — a thicker one (Jones New York) which is more of a top layer, and this medium weight one (Ralph Lauren). The latter is more of an “intermediate” layer for me; I usually wear it over a cotton tank top because it’s a little bit too scratchy against my torso (but fine on my arm skin), but still thin enough to layer under other things. Developing this arsenal of basic layers has been a game changer for me in terms of allowing to wear my favourite clothes year-round in a cold climate. It might not be minimalist to have 5-6 different turtlenecks in dark colours (which look almost indistinguishable) but they all serve their purposes and are indispensable to my closet.

Details: J. Crew shirt, vintage vest, Tabitha jacket, Laura Ashley skirt, Ferragamo shoes (all thrifted)

Thoughts: I called this Academichic Jo March, and it’s a mash-up of styles that I really enjoy in general. I thrifted this velvet vest almost 3 years ago, specifically after I saw Little Women and fell in love with Jo’s costuming, and it has served me so well since then.

Details: Club Monaco turtleneck (retail), Northern Reflections shirt, Theory blazer, Banana Republic jeans, Cotton Ginny belt (all thrifted), turquoise necklace (Poshmark)

Thoughts: This outfit is 100% a tribute to Papa Ralph himself — he has worn some version of this outfit many times (shirt over another top, tucked into belted pants, with some kind of jacket, often tweed). It was also an opportunity to test these bootcut, low rise jeans; they’re circa 2013 Banana Republic. I think I prefer the Frame flares I got recently (posted last week) but I do enjoy this silhouette too. The low rise is what I don’t love. I simply don’t like the visual proportions of it on my body. But maybe I need to just get used to seeing it. Sometimes, the more you see a “new” trend, the more it grows on you. I definitely think that the only way I would do low rise jeans again is balanced against an oversized or layered top half — not paired, say, with a tight-fitting top that will only emphasize the fact that the top part of my hips sits well above the waistband of the jeans, making me look like I’m getting squeezed out of the same.

Details: Toni T dickie, Gap sweater, Nanette Lepore jacket, Babaton pants, Ferragamo shoes (all thrifted)

Thoughts: I think I’ve mentioned before how much I love the combination of this sweater and this jacket, so I had to wear them together again. This time, with navy corduroys. I’ve never been a fan of traditional navy — it’s too dark to count as blue, and not dark enough to be, well, black. But I recently discovered this lighter, bluer version of navy and I’m really liking it. I actually had no idea that navy came in different shades — duh, like any other colour — so now I’m reevaluating my old prejudice.

Details: InWear sweater, Vince dress, Gap jacket (all thrifted), Mia shoes (retail)

Thoughts: Brown really was the colour of the fall season for me this year. I managed to squeeze in one last black-and-brown outfit before the snow hit the ground and I was forced to, regretfully, retire my beloved platform loafers until next year.

Details: J. Crew top, Zara duster, Linda Lundstrom pants (all thrifted), J. Crew shoes (retail)

Thoughts: These vintage lamé palazzo pants are quite fabulous, but I have been stuck on how to style them ever since I got them. I think it’s because they are actually a lavender-ish silver colour, not plain silver (which would be easier to pair with other colours). It would be easy enough to wear a black turtleneck with them but … that’s too obvious. The combination here — with navy and burgundy — is not bad, though.

Based on your feedback, I’m back to talk about all things Poshmark. Last time, I went over my searching strategies; today, I’m going over what I do once I’ve found a listing of interest.

I generally try to avoid spur-of-the-moment buying. Thrifting is bad for that sort of thing; you can’t “sleep” on a purchase because the item is almost guaranteed to be gone by the end of the day. It’s one of the things I dislike most about thrifting. I have become more discriminating with time, but I still have plenty of regret buys to my name. So when it comes to Poshmark, I am stricter with myself about thinking about a purchase for at least a few days before I decide to buy, unless it’s something I’ve been hunting for a long time or some truly unique and fabulous bargain (and those are rare).

So, in most cases, the first thing I do is “like” the listing of interest. This is equivalent to “watching” on eBay; it adds the listing to “My Likes” list, and allows me to be notified of seller offers, price drops, etc. Sellers are notified when someone likes one of their listings, and many of them will send an offer within the next few hours (I think this may be an automated feature but I am not sure since I don’t sell on Poshmark). These unsolicited offers are usually in the 10-15% range, though I’ve seen some as high as 30%, and often include discounted shipping. This is another reason to pause on purchases, especially more expensive ones; you might get offered a deal without even having to ask.

If an unsolicited seller offer is good – i.e. within the budget I have to spend on the item – and I am ready to commit to the purchase, then I will accept it. The reason why I don’t generally counter-offer in these situations is to avoid losing any discounted shipping the seller is offering.

Let me pause here for a moment. It’s important to note that most of my Poshmark purchases are under $50, and that is reflected in my approach. Here’s an example to illustrate what I’m talking about. Let’s say a seller has an item listed at $40. Standard shipping is now about $15 (I know, Canadian shipping costs are terrible). My preferred budget is $40 all in. The seller sends me an offer of $35 plus $10 shipping; with taxes, this comes out around $47 all in. If I use the auto-counter feature to ask for $30, my out-of-pocket cost stays the same because I lose the shipping discount. I would have to message the seller and ask them if they would accept $30+$10 shipping, and for a possible $5 in savings … well, I don’t usually bother. My decision is basically: do I like the item enough to pay $7 above my preferred budget? Obviously, if we add a zero to these numbers, the math – and my strategy! – would change.

Now, if there is no discounted shipping in play, I will sometimes use an unsolicited seller offer as a springboard to my own counter-offer. However, on a sub-$50 item, I won’t counter for small amounts; it usually has to be at least $10. Anything else feels petty to me, but this is a personal decision. I don’t usually counter-offer at all on any item that is $20 or less because I know the seller makes almost no money on that amount after Poshmark fees, though I will happily accept discounted shipping if offered, or bundle items (if feasible) to save shipping. I hate spending $15 for shipping on a $20 item! I will, however, make exceptions where it makes sense – for example, I recently paid $15 shipping for a pair of wool Paul Smith trousers after the seller dropped the price to $20, because I knew the retail value of those trousers was $$$ and I was getting a fabulous deal regardless.

Okay, let’s say I like an item but the seller doesn’t do anything right away. What next? It depends on how much I want the item and how much it costs.

If I’ve slept on it and decided that I really want it, my next move is decided by cost. If the list price is within 30% of my preferred buy price, then I will make an offer and hope for the best. If the list price is more than 30% over my preferred buy price, then I wait. Sellers will sometimes either drop the price or send offers whenever Poshmark is pushing some promotion. If an item doesn’t have a ton of likers, I will sometimes wait out 1 or even 2 price drops – taking the chance that no one else will buy the item out from under me. Sometimes, I will send my own offer following a price drop if I want to nudge the price a little bit lower.

If I decide that I like an item but not enough to commit yet, I follow the same wait and see strategy. After a few months, if the price has not dropped and my desire for the item hasn’t grown (or has, in fact, faded) then I will un-like the listing.

Let’s talk about offers. As with everything else I write here, these are simply my personal guidelines. You can adopt different ones; I don’t think there are any hard and fast rules apart from being polite (more on that in a moment). As I mentioned above, I generally do not send offers that are more than 30% below asking price. If a seller has an unreasonably high list price, I do not bother to offer. If the price is not unreasonable but still significantly higher than my budget, I wait for a price drop first rather than make an offer at, say, half price. My rationale is: if a seller tries but can’t sell at their asking price then they will be more receptive to a deeper cut.

I do not believe in contacting sellers to tell them their prices are too high; people are free to set their prices as high as they want, and I will simply avoid those which I consider out of whack. On the flip side, I do not understand sellers who get upset by “lowball” offers (unless the buyer is otherwise argumentative or persistent with repeated counter-offers). Just decline and go on with your day. If I send an offer and it’s declined – especially declined without a counter from the seller – then I get the message: either accept the original list price or move on. There was one time when I had my first (and only) offer declined AND the seller blocked me, which felt weirdly aggressive to me but I shrugged and moved on.

I also rarely counter-offer. Let’s say the list price is $70, I offer $50, and the seller counters at $60. I will not counter $50 again for obvious reasons – this is the equivalent of arguing with the seller. I will probably not counter at $55 either unless I think the item is overpriced and I’m willing to take the chance the seller will decline and nuke our conversation. To me, going back and forth over $5 isn’t usually worth it, but I am also not the haggling type in general. That being said, I almost always make at least one offer (or wait for one) unless the item is $20 or less to begin with. You never know unless you ask (once) 😊

One thing to note: Poshmark will now notify all likers of a listing when an offer has been submitted. This change hasn’t drastically affected my buying strategies but it IS something to consider in certain cases. Here is a hypothetical example: I have stumbled on a major bargain, a desirable (and authentic) designer piece with a retail price of $400+ listed for $40. Normally, on a $40 item, I will attempt an offer (most often around $30). However, if there are other likers and I know this is hot deal — and an item I know I would regret missing out on — I might forego making the offer because the notification of the pending offer might push one of the other likers to pull the trigger, and the $10 difference isn’t worth losing the piece. This has actually happened to me, from the other side: I was one of the other likers watching a piece and waiting to see if the seller sent an offer; when I saw that another person made an offer, I swooped in and bought the item at asking price so as not to miss out. This situation doesn’t arise often, but it is always worth keeping in mind that offers are not entirely private anymore (others don’t know what the offer price is, though).

One other thing to note: asking for discounted shipping means money out of the seller’s pocket in most cases as they have to cover the difference (unless Poshmark is offering a discount shipping promotion) so keep that in mind when deciding on an offer.

In general, I do not engage with buyers unless I have a question about the listing or a purchase, or they send me a personalized message. Sellers sometimes send automated messages when I like an item (e.g. “bundle to save!”), but I don’t usually bother replying. To me, it’s an annoying feature of Poshmark – the equivalent of a sales associate asking me if I’m looking for something specific as soon as I step foot in the store to browse. Similarly, I don’t send messages when I make an offer; I was surprised to read something on Reddit once that suggested it was “proper etiquette” to send accompanying messages with offers. I disagree. The app has these automated offer functions for a reason, and I am not there to make friends (sorry not sorry). As far as I am concerned, on Poshmark, etiquette primarily comes down to not wasting someone’s time; it’s why I avoid offers for less than 70% of the asking price — not because such offers are “insulting” but because they are unlikely to be acceptable to the seller and, therefore, represent a waste of time.

The one area where I do get mildly annoyed by lack of communication is when sellers ignore questions about measurements. If sellers did their job properly in the first place, IMO, all listings should include specific measurements not just brand size. I know it’s extra work, but it is such critical information when buying online; I sell a bit from my own closet (though not on Poshmark) and I always include this information when I post an item.

However, if you are in a situation where the listing doesn’t include measurements and the seller isn’t being responsive, but it’s an item you are really interested in, then I recommend searching for the piece on Google Images. Sometimes you will be able to find the original brand listing, which will include sizing information (and, better yet, customer reviews). Other times, you might find a DIFFERENT Poshmark listing (even an expired one) where the seller did post measurements. Even if it’s not the same size you are looking at, the measurements can give you a general sense of whether the item fits small or fits large. Of course, this can still be a risky proposition so you have to decide how much of a calculated risk you want to take that the item will fit properly.

I have once again written a novel, but I guess it takes a surprising amount of words to describe my very basic (hah!) Poshmark buying strategies. Hopefully, it hasn’t been entirely useless! If you have your own strategies and tips, please share with the rest of us in the comments.