Details: Babaton turtleneck, Massimo Dutti sweater, Ralph Lauren skirt, Old Navy belt, Coach bag (all secondhand), J. Crew sweater (retail, old), Mia shoes (retail, old)

Thoughts: How much did I love this outfit? A lot. I’m so excited to start shifting my closet towards spring/summer, and this was a baby step in that direction. Summer for me is all about the Trailblazer, heavily prairie-core; I will miss the layering, but it will be nice to be reunited with pieces like my vintage RL skirts (like this one) and patchwork jackets. In the meantime, I took inspiration from the skirt patterns here to pull together the rest of the outfit. Fair isle pairs well with florals (in a matched palette, of course), and I chose this plaid jacket because its grey and blue also slotted in nicely. The harmony of colours keeps everything in check, no pun intended, so it looks purposeful and not like I got dressed in the dark.

Details: Everlane turtleneck, Ralph Lauren blazer, BR pants, Fossil belt (all secondhand)

Thoughts: I have been looking for a pair of menswear-inspired trousers — something that Katharine Hepburn might have worn — for AGES. Pleated wide-leg pants have been having a moment, but for some reason, it proved challenging to find a style that fit me the way I wanted. The trouble always tended to be the pleats, and how they sat on me. But, as you can see, there is a happy ending. It was an accidental happy ending. I spotted these BR pants at the thrift store and was drawn to the heathered brown colour (very me, currently) and the cut of the leg. They were misplaced, as things often are at the thrifts, and I also didn’t have my reading glasses with me, so I misread the label. I thought it said 10, but in fact it says 16. I was about to put them back, and then I had a lightbulb moment. What if I just really, really cinch in the waist (they are very high-waisted) and see what kind of pleating/draping happens? So I did, and well … here is the result. I love it! It’s exactly what I’ve been wanting all along. The bottom of the leg is wide but not exaggeratedly so, but meanwhile there is enough volume in the top half to have a nice fluid drape — no gaping of the pleats and resulting weird poochiness. It basically looks like I’m wearing men’s trousers but, like, in an elegant (not dress-up) kind of way.

Details: Ralph Lauren shirt and skirt, BR necklace (all secondhand), J. Crew shoes (retail, old)

Thoughts: I’m a convert to the power of a crisp white shirt. Sometimes, that’s all you need to make a statement skirt into a statement outfit. And we know how much I love my statement skirts.

Details: St. John top, Jones NY blazer, Icone pants, vintage belt (all thrifted)

Thoughts: I love this trompe l’oeil top so, so much and yet constantly struggle to style it. It’s such a distinctive piece. It’s tempting to pair it with black so it becomes the focus of the outfit, but I find that ends up looking unbalanced. On the other hand, finding other good pairings is difficult because it has, well, that very distinctive vibe. I think these camel pants work quite well.

Details: Ralph Lauren sweater, Twik skirt, Fossil belt (all secondhand), J. Crew blazer (retail, old)

Thoughts: A rather sedate (for me) outfit, colour-wise, but not without a little wink. Those tights really do make the look, I think. This is the type of thing I’d be wearing if I still worked in the office all the time. It’s my current style, for sure, but toned down a little bit — but not all the way down.

Details: Wilfred sweater, Talbots vest, vintage belt, Coach bag (all secondhand), BR jeans (retail, old)

Thoughts: I have never actually shopped at a Talbots store in my life, but I own a surprising number of Talbots pieces — like this recently thrifted vest. Their pieces are surprisingly versatile, and the vintage ones are fabulous quality too. This is a more recent one, I can tell from the quality which is only so-so; but it is cool-looking, at least. I like sleeveless blazer-style toppers like this one as layering pieces for spring, and the funky houndstooth pattern gives me a lot of pattern-mixing possibilities. I kept this outfit very simple, though. Simple is nice too!

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