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.  

6 Comments on Let’s Talk Jeans!

  1. I am also in the middle of a jeans conundrum — as I’m sick of skinny jeans but having a hard time finding the perfect straight/boyfriend fit I want. I love the cut of the boyfriend jeans from your first series of photos, but I’m much curvier than you so many times ‘boyfriend’ jeans fit like skinny jeans at the top before becoming slightly more straight at the calf.

    I bought a pair of high-waisted Madewell jeans a couple weeks ago only to find out that while they look AMAZING when standing up, they are a belly straight jacket when seated!

    I’ve thrifted. I’ve poshmarked. I have an order coming from Nordstrom Rack later this week. Wish me luck…

    • Man, that’s tough! Finding jeans that work, online especially, is so hard. I’ve tried numerous pairs too. I just found another pair of flares that I quite like this weekend. Total fluke! Still looking for some palazzo jeans but the right fit seems to be a needle in a haystack.

  2. Oh dear those long wide legs + heels = some harrowing 90s memories. Be careful on stairs!

  3. You nailed some of my conundrums, and what I think much of the discourse mocking the hand-wringing over skinny jeans misses. I do recognize and accept that I now have a choice to make about trendiness, and won’t be declaring anything about “cold dead hands” about it. However, going off your points:

    1. I’m short. I’ve been managing to avoid paying to hem all my pants for years now with skinny jeans and pants, because the cropped trend plus the skinny trend plus some short lengths meant I could skate by. Now, I’m remembering how much this wasn’t the case with bootcut jeans and wincing at future tailor bills.

    2. On a related note, I’m frustrated I’ll have to spend so much more for multiple pairs of pants in instances where one pair of skinnies per color/fabric would have sufficed, because of what you pointed out about shoes. I could have one pair of dark skinny jeans, but now I’ll need a pair of dark bootcuts for flat boots, a pair of dark bootcuts for heels, multiplied across types.

    3. Many of the new jean silhouettes seem very casual (loose styles lend themselves to lots of rips, and I’m seeing a lot of raw hems). Jeans are a casual style, but dark skinny denim was a more versatile place to spend money that doesn’t seem to have a solid replacement .

    4. As you said, the relative newness of the trends means I can’t thrift or even Posh as much to offset these costs, because I just don’t know what I like on me yet and it’s not as available.

    These points make me sound like I don’t have any fun with fashion, but I think skinny pants stuck around long enough to make them easy to thrift and cheap by avoiding the above issues, which gave me the money and freedom to experiment on some fun pants once my basics were covered. I don’t feel like I’ll have that for a long time now if I have to rebuild a jean wardrobe of a bunch of hemmed, retail-priced duplicates at different heel heights, so I’m sad about that. Jeans don’t excite me in the way, say, dresses do, so it feels like a chore in a way fashion really hasn’t ever.

    • I understand your frustration. Personally, I’ve made peace with the idea that I will have one of each style of jeans and only wear it with one type of shoe (heel or not). I have enough other options so it’s not a dealbreaker not to have bootcuts for heels and bootcuts for flats. But I want bootcut to create that long leg line so heels makes sense for me in that context. I appreciate that may not work for others.

      I should also mention that cropped flares are an option! I actually saw that Carolyn Bessette wore them too and I just found a vintage-ish pair from Tommy Hilfiger. So that can be an option as an alternative to skinnies that may not require hemming. It’s a different silhouette but one that’s still trendy (and apparently was trendy in the late 90s too).

      Ultimately, as you noted, it’s really a personal choice. In the dead of winter, I will probably wear my old pair of skinnies if I have to trudge in snow because I can tuck them into my heavy winter boots. You gotta do what works!