Details: J. Crew top, Line sweater, Marc Cain skirt, Chelsea Crew shoes (all thrifted), Ralph Lauren blazer (Poshmark)

Thoughts: I almost got rid of this skirt last year because I wasn’t quite ready for mini skirts then. I ended up keeping it because it’s such good quality and, boy, I am glad I did. I’ve enjoyed experimenting with this silhouette again this year; I think the key to making it work for me is opaque tights. Then I can adapt it to my Historian/Witchy Academia aesthetic for fall, as an alternative to midi skirts or pants. I quite enjoyed the warm tone palette of this outfit — it’s surprisingly (to me) flattering to my complexion and colouring. I think I look best in cool colours but maybe it’s not quite absolute?

Details: J. Crew shirt, Gap sweater, BDG pants, Jil Sander jacket (all thrifted), J. Crew shoes (retail)

Thoughts: I’m also rediscovering my Gap striped sweaters — paired with a button-up shirt, they fit my current aesthetic really well. This isn’t quite Witchy Academia, but it’s fun.

Details: Denim & Supply dress (Poshmark), Everlane sweater (thrifted), BlankNYC jacket (retail), Ash sneakers (thrifted)

Thoughts: This outfit gave me strong 90s grunge vibes, which I loved. I was nowhere near stylish as a teen in the 90s, so getting to re-live that fashion moment now is nice.

Details: MSGM sweater, Tabi skirt (both thrifted), Club Monaco turtleneck (retail), Ash sneakers (Poshmark)

Thoughts: Green and orange is a bit of an odd duck combination. I took my cues from this varsity-style sweater and added the skirt because it has similar colours. The result is more student than professor, but it’s still sorta academichic-adjacent, right?

Details: Club Monaco turtleneck (retail), no name cardigan, Tommy Hilfiger jeans, Brave belt (all thrifted), Mia shoes (retail)

Thoughts: I don’t normally thrift Shein-equivalent fast fashion — which is what this cardigan is, I’m pretty sure — but I made a (reluctant) exception in this case because I liked the looks of it. The quality isn’t good but I plan to keep this piece in circulation for as long as I can. It’s a good piece to throw on for super casual errands (like school pick-ups) when I still want to look cute. It takes a super basic outfit and makes it a bit more interesting.

Details: Wilfred sweater (retail), Tradlands jacket (thrifted), Ralph Lauren skirt (swap), Chelsea Crew shoes (thrifted)

Thoughts: Purple and green are my villain colours — I feel like a badass when I wear them together — but they felt subdued in this outfit by the addition of the whiskey/tobacco brown. Is this a bit too matchy? Possibly. This outfit felt like it was on the edge of greatness (haha) but not quite there. I’m not sure what would have taken it over that line, but ah well. It was still pretty cute.

Details: Max Studio dress, Frame blazer, BR belt (all thrifted), Club Monaco turtleneck (retail), Mia shoes (retail)

Thoughts: I’ve been thinking about this outfit since the summer when I thrifted this dress. It’s transitional dressing at its most appealing (to me). The addition of the velvet blazer, together with the turtleneck, totally changes the vibe of the prairie dress. You may have noticed that I wear these Club Monaco turtlenecks a lot. I have them in 2 colours: dark green and dark purple. They are very fine, lightweight, super soft merino wool; they are so thin, they are slightly sheer, which makes them perfect for layering. I wear them as a base layer because they are not scratchy or bulky at all. They’ve held up very well over the past 4 or 5 years (handwash and air dry, always) and I so wish I had bought more at the time or could find something similar again. They’re a staple of my fall and winter closet.

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.