Details: Toni T dickie, Everlane sweater, Ralph Lauren skirt, Ash sneakers (all thrifted)

Thoughts: My favourite fall outfit so far — a few people called it “Wednesday Addams grows up” and I love that. I also got a random compliment on it from a woman in a store parking lot so you know this outfit has presence. I rarely repeat exact outfits head to toe, but this one will be a repeat for sure. Simple, comfortable, totally “me”.

Details: Toni T dickie, Pilcro sweater, Gap jacket, Cartonnier pants (all thrifted), Mia shoes (retail)

Thoughts: Another favourite fall outfit. I love the purple-lavender-whiskey colour palette. This is going to be one of my go-to outfit formulas: button up shirt+sweater+pants (or skirt). Finding this white collar dickie was a true godsend; it allows me to pull off that layered look without any extra bulk. Once the temps nose-dive, I’ll wear a proper white shirt as a layer but, for now, this is just the ticket.

Details: Braemer vest, Ralph Lauren shirt, Zara skirt (all thrifted)

Thoughts: You didn’t think I would forget about vests, did you? No way. It’s time for my fall vests to come out. I’m still a huge fan of them as a “completer piece” for WFH outfits where a jacket feels a bit like overkill most days (but I still want that 3-piece outfit).

Details: Aerie top (retail), Judith & Charles jacket, vintage pants (both thrifted), Stella & Dot necklace (Poshmark)

Thoughts: I am also not forgetting my crop tops! I’ve been thrifting some high waist pants — like this fun patterned pair — that will be perfect for taking this outfit formula into fall and even winter (WFH, remember!). Elastic (high) waist, pull-on pants are the epitome of easy dressing for me; they can be dressed up and down equally easily.

Details: Tabi vest, Tradlands jacket, Babaton skirt, Ferragamo shoes (all thrifted), Echo scarf (consigment)

Thoughts: Finally got to try out a new-to-me brand — Tradlands — thanks to this thrifted jacket. It’s a wide-wale corduroy, which is one of my current obsessions — I love this texture for fall. It’s also a colour that works really well with my fall wardrobe. I thought this scarf was a nice complement to the vest, as they share colours but also offer a bit of contrast.

Details: Wilfred sweater, Ralph Lauren shirt, Babaton pants, Mackage jacket (all thrifted), Mia shoes (retail)

Thoughts: I was going for a monochrome look (these newly thrifted pants are a great match for the sweater I thrifted last spring) and decided to add another colour at the last moment. I think the dark plum jacket complements the blue nicely. As I said, I am obsessed with corduroy at the moment, so I was pleased to find these cord pants in a cropped style that works well with my favourite new shoes (plus, they were only $4!).

I know jeans can be a fraught fashion topic in some circles today. To skinny jean or not to skinny jean? I am not going to tell you what your answer ought to be. They aren’t trendy (and haven’t been for years) but that only means something if trends are something you choose to care about. I do and I don’t – I’ve talked about this before. I like to know what’s out there so I can better decide what I can use to create the aesthetic I am pursuing. But I’m not adopting the trend unless it works for me, for that purpose.

As it happens, I’ve mostly moved away from skinny jeans in recent years. This past summer, loose-fit boyfriend style jeans were my usual go-to:

With the occasional assist from this barrel-shape/80s mom jean-adjacent pair:

These styles worked better for my summer aesthetic than skinny jeans. I still have a couple of pairs of skinny jeans, and wear them occasionally, but usually for very casual errands (like taking the kids to the park) where aesthetic doesn’t come into play.

Looking at my fall inspo boards, I realized that I needed to consider some other jean styles. Because my fall aesthetic is heavily influenced by the 90s and Ralph Lauren “prep”, I settled on two related styles:

One. The bootcut flare – think Carolyn Bessette Kennedy:

Two. The trouser/palazzo jean:

Initially, I thought I would only need the first kind (in a dark wash, natch). After some further deliberation, I decided that I really wanted to give the palazzo-style jeans a try too, and likely in a lighter wash for diversity.

Some additional considerations:

• Bootcut flares of the OG variety (late 90s through late 00s) are relatively easy to source in thrift stores. I’ve found a Banana Republic pair that I am currently taking through its paces and deciding whether the fit is precisely what I want. I may end up trying to find something with a slightly more pronounced flare, but we’ll see.

• Palazzo jeans are not very easy to find at the thrifts, as they were not a super popular/trendy style within the past 10 years. So I am leaning towards possibly sourcing a pair on Poshmark or even retail. Buying a new style online can be tricky though, not only because you need to ensure the proper size fit, but also to gauge whether the style meets one’s exactly requirements (usually from a bunch of stock photos). Wide leg jeans have been popular for a while, but the style I am after is a more specific sub-category of that.

• Both of these styles need to be full-length, i.e. not cropped, to achieve the desired aesthetic. In particular, because I want to have that elongating effect (and have a short inseam), this means having to consider heel height. In the summer, I tend to wear flats which would pose a problem in this scenario. But for fall, I do have shoes with more of a heel – like my new platform sole loafers, for example, and some of my favourite ankle boots as well.

• Full length jeans can pose a hazard during wet conditions so I know that these jeans will have a limited time window; I don’t expect that I will be wearing them outdoors come November. This is something to consider when deciding how much money I want to spend on them (answer: not a lot!).

I’m writing all this out because I think it’s helpful when making decisions about adding new pieces to one’s wardrobe to think through stuff like this. Hopefully, it’s helpful to some of you as well; not as a “what you need to buy” post, but as an example of process. I have been trying to be more intentional about what and how I add to my closet, and I’m probably not the only one. Share your tips — and thoughts on jeans! — in the comments.