Details: Babaton turtleneck, Supply & Demand tee, Frye belt, unbranded skirt, Levi’s jacket, Ricki’s bag, Laredo boots (all secondhand)

Thoughts: This outfit was so good, my daughter borrowed it afterwards. I am not joking. She wore the exact same thing, minus the accessories. I can hardly blame her, because it’s one of my fave recent outfits. I just can’t get enough of this slate blue paired with grey and black. Obsessed is an understatement. We are also obsessed with this Levi’s jacket. I was originally on the fence about spending $25 on it at the thrifts, but it has paid off over and over again.

Details: Tahari shirt, Pitlochry sweater, Ralph Lauren jacket, BDG jeans, Land’s End bag (all secondhand)

Thoughts: I love the 70s academia vibes here — and, of course, the colour palette. You may remember how long I spent looking for the perfect pair of palazzo-style jeans before I finally found this one; it was worth it. BDG is actually a brand I always keep an eye out for at the thrifts, not because the quality is phenomenal necessarily, but because they’re a youth-oriented brand which means that they tend to offer a wider selection of trendy pants, especially jeans. Some of them are terrible, but I’ve found a few gems — styles that I wasn’t able to find from other brands. And have you noticed the bag? I saw a blue suede bag in someone’s Reel a few months ago and instantly fell in love. It’s a more saturated version of my slate blue. (See how I just assumed ownership of that colour? Hah!) Anyway, the bag I originally saw was Michael Kors and the only listing of the same style I was able to find on Poshmark expired before I pulled the trigger. But then I found this very similar style — in the same shade of blue — from, of all things, Land’s End. And it was less expensive, score! The downside was having to wait while it sat in some depot during the month-long postal strike in December, but when it finally arrived … it was worth the wait.

Details: Babaton turtleneck, unbranded dress, Wilfred shacket, Ricki’s bag, Laredo boots (all secondhand)

Thoughts: This outfit? Nothing special … just the turtleneck/dress combo I’m utterly obsessed with at the moment. And one of my favourite bags to make up the colour combo I simply can’t stop wearing. No biggie.

Details: Nomi turtleneck, unbranded cardigan, Club Monaco skirt, Brown’s shoes (all thrifted)

Thoughts: I remember when Club Monaco rolled out the collection featuring this iris print. I coveted the dress, but it was pricey (even on sale) and by then I was already a dedicated thrifter with an aversion to paying retail prices. Fast forward about a decade, and here we are: as soon as I spotted this skirt at the thrifts, I knew I had to get it. One, because I adore irises. And two, because of the nostalgia factor. Y’all know I’ve sworn off pencil skirts — BUT — this purchase wasn’t a cheat because it’s short enough not to count as such, in my books anyway. I’m officially classifying it as a mini skirt. A mini skirt, for me, means tights. I recently saw someone talk about what kinds of tights go with what kinds of skirts, and it had to do with the skirt fabric. Basically, they said that if the skirt is silk, you should wear sheer or semi-sheer tights not opaque ones; conversely, if the skirt is a thicker, chunkier material, you should wear opaque tights not sheers. I have no idea if this is some universally known truth — or even categorically true — but it was news to me, and I like the results when applied. So here we are. Make of it what you will.

Details: Babaton turtleneck, Smythe jacket, Mondi skirt, Chicwish skirt, Donna Karan belt (all thrifted)

Thoughts: I know I’ve made fun of beige in the past, and it’s still not my favourite colour by a long shot, but I think it’s possible to make it not-boring. This was an attempt, by moi.

Details: Ralph Lauren shirt & vest, Hudson skirt, Nocona belt (all secondhand)

Thoughts: I was unsure about buying this skirt. I have a LOT of skirts. I need one less than a fish needs a bicycle. But I’m a sucker for this tiered maxi style, and the colour intrigued me. It was $7 at Goodwill so I allowed myself to be swayed — not the best approach, admittedly, but I’m not perfect (at thrifting or life in general). It remains to be seen how much wear it will actually get, because with a closet as large and diverse as mine, it’s a matter of diminishing returns per item; but there is no question that the skirt checks off a lot of important boxes. This outfit is good evidence of that. Also of the power of a men’s white shirt. Ahh, summer: you can’t come soon enough!

Details: Babaton turtleneck, Chaps vest, BDG jeans, vintage belt (all secondhand)

Thoughts: I don’t normally buy Chaps or long vests, but something about the colours of this one appealed to me. Well, I’m pretty sure that “something” is the slate blue/red combo because … do I even need to explain anymore? Anyway, my challenge now is to figure out how to style it in a way that works for me, despite it being outside my wheelhouse. I liked the simplicity of this attempt. Notice how those BDG jeans came in clutch again. Also, shoutout to my cream turtleneck that I practically wear non-stop these days. I’ve abandoned my black turtlenecks and discovered a whole new world of possibilities. This cream one is the most versatile new option — I think of it as the fall/winter equivalent of a white tee.

Details: Tahari shirt, Uniqlo sweater, Coach bag (all thrifted), J. Crew blazer, Zara pants (both retail)

Thoughts: I’ll leave you with this “casual mom” fit featuring a blazer that’s more than a decade old and still continues to elevate every single outfit I throw at it.

Today, we are going back in time to 2013, a year I predominantly growing out the previous year’s ill-considered pixie haircut and being pregnant and, thus, in various degrees of discomfort. I remember struggling a lot to find cute maternity clothes, and making do by buying oversized regular stuff, mostly dresses. This was a time when I was starting to be obsessed with Anthropologie and J. Crew – cute, twee, colourful stuff. Everybody wanted to be Zooey Deschanel back then, ok? Not an aesthetic particularly adaptable to pregnancy, so you can understand why I struggled. But at least my bag game was on point.

Let’s take a look!

Pour one out for these three bags I no longer own. I only regret one of them. Can you guess which one? I sold the black Chanel one so I could buy a different version (which I still have), and the Mulberry Alexa never really did it for me, but the Coach? Ahhhh, she was a beauty and she is missed.

This collage is a pretty good cross-section of my 2013 style, attempting to translate my whimsical pixie dream girl aesthetic to my dichotomous downtown lawyer/suburban mom lifestyle. There were some hits, and many, many misses, I have to say. Proof that an eye for personal style is developed, not bought. And in 2013, I was still at the beginning of that journey. That being said, these outfits were terrible; at worst, they are of their time. Skinny jeans, round-toe ballerina flats, colourful statement necklaces, skinny belts, ‘nude’ shoes – they were inescapable in 2013, and we all thought they were the cat’s pyjamas. Don’t even try to tell me otherwise; I’ve got Tumblr to back me up.

Anyway, here’s the 2024 version:

The overall effect is very different, but a lot of the elements are actually quite similar. Minus the J. Crew bauble necklace, which I don’t propose to revisit any time soon. But look: button up shirt, check. In 2024, we are doing texture and layering. Belt, check; but chunkier and with a fun buckle. (Statement buckle, not statement necklace could be the slogan of 2024, hah!) Pencil skirt, check; but longer, always. Fun fact: I’m actually wearing this Ralph Lauren skirt backwards, because having the slit in front makes it a little edgier. As for the accessories, they’re also not dissimilar. I wouldn’t wear ‘nude’ shoes anymore, but these beige-and-black ones are so fun. You can’t see the bag I’m wearing in the right-hand photo, but it’s a small crossbody Dooney. It has the structure that the Alexa didn’t, but a similar vibe.

Again, I chose a current outfit that incorporates a lot of similar elements, but to different effect. Instead of a striped top, I chose a (cotton) striped sweater; both are J. Crew, and actually from the same era (2013-2014). In both cases, there is a white underlayer, but for different reasons. The 2013 striped top wasn’t maternity and, thus, not long enough to go over my bump; a longer, plain tank covered the gap. In 2024, I am all about the high-waist life, so everything is tucked in – but I’m also all about layers (for the sake of fashion, not exclusively function), and a pop of white collar always works. Jeans, check. Obviously, the silhouette is different and makes a big (visual) impact. Skinny jeans are starting to make a comeback, but I am not ready to go (back) there again. Flats, check; but instead of ballerinas, I’m wearing loafers.

And, last but not least, 2024 has (i) a belt, of course, and (ii) a third, ‘outfit completer’ piece, the trench. The power of the third piece cannot be underestimated. In terms of “styling” an outfit, it makes the biggest impact. One area of my wardrobe that has expanded significantly since 2013 is my coat collection; I have different styles in different fabrics, so I am never short of options for my ‘outfit completer” piece, no matter the season.

The dress-with-blazer formula used to be a big favourite back in my law office days, but these days, I tend to prefer separates. Still, the biggest different between these outfits is (a) the style of blazer, (b) the length of the dress, and (c) the styling of the whole look. These days, if I wear a classic, structured blazer that hits at hip level (as in the left photo), it’s always in a heavier wool or tweed material, and never in suiting wool or ponte. In general, I tend to gravitate towards jackets that are either cropped and boxy, long and lean, or oversized. If I’m wearing a mid-length cut, it’s usually in an unstructured, non-traditional cut, like the photo on the right.

Of course, the difference in hemlines should come as no surprise. I spent altogether too many years wearing just-below-the-knee dresses and skirts, which is probably the worst choice for someone like me, who has short legs and a long torso and would like the world to believe the opposite. These days, it’s the 3 Ms or bust: mini, midi, or maxi. Midi is my current favourite, and specifically mid-calf, like the skirt on the right.

As for styling, the differences are small but important. My focus is on subtle details, like belts or a touch of layering, to add balance, depth and visual interest. I went through an overtly maximalist phase back in 2020-2022, but that chapter is now closed, at least for the time being. While maximalism remains part of my style DNA, it manifests in different ways now: layers, texture, richness of colour and materials, minimal but impactful accessories. The eye has developed … and it continues to develop.

Details: Chepe dress, Rebel Sugar turtleneck (both retail), Chicwish skirt, vintage belt, Rafael Alfandary necklace, Thierry Raboutin shoes (all secondhand)

Thoughts: I’ll always be a gothic girl at heart — not when it comes to literature, but definitely when it comes to aesthetic. Give me a tumbledown castle overrun with ivy, books, and the odd ghost, plunk it down in the middle of a misty autumn, and sprinkle an air of melancholy over the whole thing, and I am HOOKED. In lieu of all those things, this outfit will do. Gothic is a state of mind. As a more practical matter, I am here to remind you again that tulle is the perfect insulator, in addition to its other advantages. It has been helping me transition many a summer skirt and dress into other seasons, which is very nice of it, indeed.

Details: Babaton turtleneck, vintage dress, Akris jacket, Banana Republic belt (all thrifted)

Thoughts: I loved this vintage silk dress from the first moment I saw it on the racks at Goodwill, and I have not had cause to rue my impulse since. The cut paired with the fabric works for me very well, skimming the body and elongating the vertical line. But it’s the print that makes it special — the brown, black, beige colour palette is one of my current obsessions. It’s much more than the sum of its parts; none of those colours, on their own, would be especially interesting (apart from brown, perhaps) but they come together in a very satisfying way. They also go well with many of my fave colours, like sky blue and red, though you’ll have to wait to see proof of that … soon 😉

Details: Calvin Klein tee, Mexx cardigan, Banana Republic pants, Tristan belt (all thrifted)

Thoughts: More proof that black and brown, paired with a light neutral, is a combo that punches above its weight. A simple outfit that made me feel more chic than the effort involved in putting it together warranted.

Details: Gucci blouse, Uniqlo sweater, Joe Fresh pants, Manolo Blahnik shoes (all secondhand)

Thoughts: When I realized that the colour of my fave sweater was an almost exact match for the colour of this Gucci blouse (one of my best ever thrift finds, RIP Golden Era of Thrift), I simply had to make this pairing happen. I wasn’t sure at first how to complete the outfit, but then I came across these cropped corduroy pants at the thrifts, and I knew I’d found a good contender. The orange-toned brown is a lovely complementary colour for blue. The pants are nothing special — I don’t usually thrift Joe Fresh — but they were inexpensive so I grabbed them because the style works well for me in the winter; I can wear them with any type of boot, and not have to worry about tucking in the leg or bunching.

Details: Banana Republic turtleneck, Guns ‘n Roses tee, Tommy Hilfiger jacket, Banana Republic jeans, Fossil belt (all thrifted)

Thoughts: I’m not a massive GnR fan, but the colours of this (reproduction) concern tee were just too good to pass up. Decided to lean into the 90s vibe and added this vintage Tommy leather jacket into the mix. This winter has been mild enough at times to almost be enjoyable, fashion-wise, but I am still MORE than ready for spring to come so I can wear something other than these boots all the time.

Details: Tabi sweater, Ralph Lauren skirt, Suzy Shier coat, vintage bag (all thrifted)

Thoughts: Polka dot on polka dot action. Polka dot redux. All polka dot, all the polka time.