Details: Rixo dress, Amaryllis jacket, Chloe shoes, Anna Paola bag (all secondhand)

Thoughts: My social life is only occasionally exciting, so I make the most of my opportunities to dress up. A dinner with friends, with a side of drag show and burlesque, was definitely an opportunity not to be missed — sartorially and otherwise. This Rixo dress I recently thrifted at Goodwill seemed like the perfect bold choice. I chose the other pieces, including accessories, to complement the dress: leopard jacket, green bag. I used to wear opaque tights exclusively, but I’m currently digging sheer black nylons as a cool(er) weather practical accessory. At least until the snow hits, hah!

Details: Club Monaco vest, Zara blazer, Ralph Lauren skirt (all secondhand), J. Crew shoes (retail, old)

Thoughts: A layered, textured monochromatic brown moment. The longer vest/shorter jacket combo was a bit of a “climb out on a limb” choice, but I think it turned out quite nicely. And I took a further risk by choosing green, rather than brown, tights. I felt like the outfit needed something extra, and when in doubt, a pop of colour isn’t a bad bet — though, in this case, I didn’t want anything too stark or contrasting which might unbalance the colour palette.

Details: Club Monaco sweater, Michigan Rag Co jacket, Fossil belt, Dooney bag (all secondhand), Zara pants (retail)

Thoughts: I have collected so many wonderful coats over the years, it’s sometimes a challenge to find time to wear them all regularly. But I try to give each one at least one outing per season (and, of course, some get much more frequent wear) and it was time for my Bird Coat aka the Jessica Fletcher Special to make its fall appearance. It might not be my most versatile coat, but I love it so dang much! In the past, I’ve worn it with jeans, but I thought these brown Zara pants would be a nice alternative. TBH, they’re a nice alternative in a lot of cases … which is why I bought them. And I like to feel vindicated in my decisions, so here we are.

Details: Tahari shirt, Ports International blazer, Auxiliary belt, Liz Claiborne pants, Tommy Hilfiger bag (all thrifted), Mia shoes (retail, old)

Thoughts: I told you I would be wearing these white pants until the bitter end weather makes it impossible, and I am a woman of my word. Beyond the fact that they’re supremely comfortable and look great, it comes down to white. White is such a fabulous pairing for brown and blue — separately or together — and we all know how I feel about those colours. I don’t own a lot of white clothing (because I’m a klutz, I’ve avoided it for years) so I have to make the most of the items I do have. And if that means wearing these pants ad nauseam, well, so be it.

Details: Tahari jacket, Ralph Lauren skirt (both thrifted)

Thoughts: I love the Dior New Look vibe of this vintage jacket (probably 90s, but definitely retro-inspired) and I am forever looking for ways to emphasize it. My favourite swishy skirt plays the supporting role here nicely, I think. Bonus points for the green and blue palette, which never disappoints me. The overall energy here is what I’m calling Not-So-Dark Academia.

Details: Tommy Hilfiger shirt, Jones Collection sweater, Babaton pants, vintage belt, Ferragamo shoes (all thrifted)

Thoughts: I wrote about my fave colour pairings last week, and here’s another one of them: navy and dark green. With white as an accent colour, just imagine 😉

Details: Tahari tee, A&F cardigan, Fossil belt, Eddie Bauer pants, vintage shoes, Coach bag (all secondhand)

Thoughts: Super casual look, elevated with cool accessories. I thrifted this vintageish layered necklace and am obsessed with it as a subtle statement piece. Or is that an oxymoron? I know that piling on multiple delicate necklaces is trendy again, but while I don’t mind layering bracelets, I hate fussing with multiple necklaces. How do people keep them from getting tangled?? Anyway. A piece like this that does all the work for me? Genius. Love it. Also brilliant? These vintage shoes. They are definitely from the 90s, and my teenager self approves of them whole-heartedly. The square toe, the chunky strap, that gorgeous oxblood colour: what’s not to love?

Details: Club Monaco sweater, Liz Claiborne pants, Mexx belt, Ralph Lauren shoes, vintage bag (all thrifted)

Thoughts: It is very brave — or very foolhardy — for someone as klutzy as me to wear head-to-toe white. Sometimes hubris pays off, though. I felt pretty freakin’ fabulous in this Nancy Meyers-coded outfit … aaand I managed to avoid making a mess of myself. I broke one of my rules in buying this vintage Club Monaco sweater, as I already have a very similar white cable knit sweater, but I have no regrets because it’s fabulous. Also, it’s a turtleneck, which the other sweater isn’t, and a slightly different shade of white. Justifications, I have lots of them. Anyway, I wanted to keep the outfit very simple, to allow the details of each piece to shine, so I kept the accessories minimal — with the exception of the bag, which was more like the cherry on top of the merengue here.

Details: Calvin Klein tee & jeans, Ralph Lauren trench & shoes & bag, Gap belt (all secondhand)

Thoughts: I haven’t worn a trench coat in years, but the vibes are finally vibing again; it’s a classic piece that fits right into my current style mood. By one of those lucky coincidences that sometimes bless the dedicated thrifter, I stumbled on the perfect tan trench at the tail end of summer — and it’s Polo Ralph Lauren to boot. It instantly elevates the most basic of outfits, and you can’t get more basic than a white tee and jeans. Another take on 90s-inspired minimalism.

Details: Ralph Lauren shirt & sweater, Brighton belt, Danier skirt (all thrifted)

Thoughts: I am very much into this blue, white, brown colour palette at the moment, and I simply had to build an outfit around this suede maxi skirt. It never fails to deliver. I decided to take another page from Papa Ralph’s playbook, and pair it with preppy pieces — plus a western-style belt. Mixing genres is one of the things that he does best. His most recent runway collection (SS 2025) provided lots of food-for-inspo on that front.

Details: Tommy Hilfiger shirt, Ralph Lauren vest, Sag Harbour pants, Fossil belt, Ferragamo shoes (all thrifted)

Thoughts: Another colour combo I’m loving at the moment is navy and dark green. How amazing are these vintage wool pants? And they’re lined, which is a bonus that can’t be discounted in these days of declining quality. I find that the key to making this colour palette work is avoiding black and using brown as the base neutral instead. Brown sets off darker blues and greens so much better than black, so they pop instead of looking muddled.

Details: vintage sweater, Auxiliary belt (both thrifted), Zara pants, J. Crew shoes (both retail)

Thoughts: I’m not sure if I’ve ever done a fully head-to-toe brown outfit before, but this one was a first-class effort, whatever the case. Adding several shades of the same colour gives an outfit depth, while different textures give it visual interest. The leopard print belt was a last-minute addition, but I thought it would be fun to sneak in a little bit of (trendy) pattern.

Details: Zara top, Danier vest, Jones NY blazer, Elisa Fanti skirt (all secondhand)

Thoughts: I’m loving suede vests at the moment, and this deep red one is *chef’s kiss*. I would normally pair with pants, but decided to give it a try with a skirt — and a classic pencil skirt at that. Paired with a blazer, it turned out quite well; without, I am not quite loving the visual effect of the short sleeves, so that’s an element I’d probably workshop a bit more next time.

Details: vintage sweater, Ralph Lauren skirt, Coach bag (all secondhand), Mia shoes (retail)

Thoughts: I have been looking to add some brown to my sweater collection — at this point, the only part of the wardrobe where that colour isn’t (yet) represented — and this vintage chenille sweater was my first find. I love the colour and texture, plus it’s soft and cozy. Paired with this 90s RL silk skirt, it makes for a fabulous transitional outfit. My platform loafers are still going strong heading into their 3rd (!) fall season.

Details: Banana Republic dress, Sonoma belt, Canadienne boots (all thrifted), Icone shirt (swap), Coach bag (Poshmark)

Thoughts: As soon as I saw this vintage chocolate brown velvet mini dress, I had flashbacks to my teenage years. Appropriate since, according to the inside tag, this dress is from 1992. My 12-year old self would have TOTALLY loved this … but might have been too self-conscious to wear it. As it happens, my 44-year old self has no such qualms. I went all in for the 90s vibes, with tall, flat-heeled boots and this chunky belt that is, apparently, also making a comeback at the moment. Don’t buy the Urban Outfitters version; check out your local thrifts and get the original.

Details: Ralph Lauren sweater, Fossil belt, Ferragamo shoes (all thrifted), Zara pants (retail), GoGo bag (retail)

Thoughts: Not one but two new retail purchases in this outfit — that must be a record for me this year. I wanted a new belt-bag style, canvas crossbody because my daughter stole my old Herschl one, and sometimes I need a lightweight, easy-zip bag option for errands and such. I found this one at Winners, and it’s cute enough to dress up and down. I dressed it up a bit here, although this outfit still falls firmly on the “casual” side of my style spectrum. The pants are also new, current season Zara. I popped into the store recently to scope out the new trends — it’s one way to stay on top of things, and know what to look for at the thrifts — and unexpectedly fell in love with them. Specifically, with the silhouette. It’s a subtle barrel shape, which I love because it’s giving me a taste of that trend without being too overtly trendy, which makes them more versatile in my book. The dark brown colour is also perfect for my wardrobe, as I am slowly replacing black as my core dark neutral.

Details: Bozzolo tee (retail), SmartSet dress, Ralph Lauren vest, Ann Marino shoes (all thrifted), Ralph Lauren bag (Poshmark)

Thoughts: Another very 90s outfit, featuring a mix of vintage and current pieces. Dark blue/navy is another neutral I am exploring this season. I love it paired with white as well as brown, both of which are core colours in my palette now. Other colour pairings I’m planning to try are navy/dark green and navy/dark red. Stay tuned.

Details: Reitmans tank, Ralph Lauren blazer, Liz Claiborne pants, Holt Renfrew belt, Ferragamo shoes (all thrifted)

Thoughts: Speaking of navy, white, and brown — here you go. I loved this outfit so much, despite the fact that my husband went around calling me captain of the Love Boat all day. He’s just jealous. Also, he mostly lives in sweatpants, so what does he know. Anyway, I continue to be obsessed with these vintage Liz Claiborne pants, and to wear them constantly. Luckily, my spill-free streak also continues. Hope I didn’t jinx myself just now …

Details: Calvin Klein tee and jeans, Donna Karan belt, Ferragamo shoes (all thrifted), St. John jacket (swap), Coach bag (swap)

Thoughts: The gamble I took with these bootcut jeans is starting to really pay off. I’m loving the silhouette and exploring its possibilities in different outfit formulas. Here, I paired it with this vintage knit jacket for a juxtaposition of ladylike and 90s minimalism which, I think, was quite successful.

Details: Ardene top (retail), Bianca vest, vintage coat, Do+Be skirt (all thrifted), Dooney bag (Poshmark), Mia shoes (retail)

Thoughts: Still playing around with leopard print and exploring its pattern mixing possibilities. I love pairing it with a lighter colour palette like this one — white/cream and browns. It appeals more to me than a pairing with black, which to me makes the leopard print look more stark and in-your-face. I enjoyed this layering moment, and specifically the addition of the suede vest as a middle layer. The textural contrast is very nice.