Details: Max Studio top, Esprit belt, Ralph Lauren skirt, Old Navy shoes, Coach bag (all secondhand)

Thoughts: One of the favourite outfits of this summer, and I can say that with my full chest. I felt like a (prairie) princess in this outfit. Whenever I wear this skirt, I am always thankful that I decided to pull the trigger and splurge on it last year, because it brings me so much joy.

Details: Ralph Lauren shirt, Roughrider vest, vintage belt, J. Crew shoes (all secondhand), Ricki’s skirt (retail)

Thoughts: Wearing all white is tempting fate to the nth degree, but I did it. On a WFH day, because I don’t trust myself with this kind of outfit in public. I’m calling it a win because, not only did I NOT spill anything on myself, I looked pretty fab too (if I do say so myself). There is something so elegant about an all-white outfit paired with strategic accessories.

Details: Zara top, Icone shirt, UO skirt, Napoleoni shoes (all secondhand), Icone belt (retail)

Thoughts: I wanted to take this skirt in a Papa Ralph-approved direction, and make it summery at the same time. Plaid is more of a fall/winter pattern to me, so the top half of the outfit had a lot of work to do. I think the crop top + chambray combo managed to pull it off. I like how it’s the reverse of a typical lumberjack chic outfit — plaid on the bottom, denim on top. If I had worn this outside, I’d have gone with some cowboy boots for sure.

Details: Ralph Lauren shirt & sweater, Twik skirt, vintage belt (all secondhand), J. Crew shoes (retail)

Thoughts: I thought this outfit punched way above its effort level; it’s pretty basic, but it looks so sharp. I wore this on one of my rare office days … and I ended up being the only person there, which means nobody got to see this IRL. Sad. Well, at least you get to see it here.

Details: Sandro top, Lord & Taylor cardigan, UO pants, Saint Laurent belt (all secondhand)

Thoughts: This is the kind of very traditional outfit formula that I rarely wear these days — I have, like, 2 classic cardigans in my closet — but I made it feel exciting (to me) by adding an edgy metallic belt and a crop top that showed a tiny sliver of skin. Ooh la la! I have to say that the combination of magenta and black is also really nice and sharp; the two colours play off each other very well.

Details: Charlie Holiday dress, Roughriders vest, cowboy boots, Brixton hat, Lena Bernard necklace, Coach bag (all secondhand)

Thoughts: Simple summer style — maxi dress, vest, cowboy boots. I think I’ve been wearing cowboy boots almost as often as sandals this summer, which is an interesting turn of events for yours truly. But I’m leaning into this vibe, and enjoying the heck out of it. Turquoise and red accessories to finish off the fit; it’s a combination that never lets me down.

Details: Ardene top (retail), Silverado jacket, Cotton Pickers skirt, cowboy boots, Coach bag (all secondhand), Icone belt (retail)

Thoughts: I love this jacket so I take every cool-weather-day opportunity to wear it. I should branch out and try different colour combinations for it, but it’s hard to resist defaulting to white and blue. It looks so good! I’ve been debating whether this vintage skirt is special or unique enough to keep in my (crowded, so crowded) closet, but this outfit convinced me to give it another reprieve. Come fall, though, some tough decisions will need to be made. I am not looking forward to it, sigh.

Details: Chaps tee, Denim & Supply jacket, UO pants, vintage belt, Manolo Blahnik shoes (all secondhand)

Thoughts: Southwest-inspired, but make it business casual. I wore this to WFH, but I could easily bring it to the office. It’s a rather muted colour palette for me, but the sequins and metallic mesh belt add some visual interest. I don’t buy a lot of sequins these days, but I picked up this tee because I thought it was a nice, subdued way to do sparkle. Like, daytime sequins. It’s good to have some of those on hand. You never know when you might need to zhuzh up an outfit.

Details: Zara top, vintage skirt, Aldo shoes (all secondhand), Prairie Trail Goods jacket

Thoughts: Patchwork, doubled. The jacket and skirt are made for each other, aren’t they? I chose the platform loafers as a bit of a wildcard pairing, and strangely (or not, I did put some thought into it) I was very pleased with it. I like the juxtaposition; the vibe of the shoes adds a more contemporary edge to the outfit. And the colour is soooo versatile. These shoes were a solid addition to my closet — just like my brown and black pair.

Details: Liz Claiborne dress, Le Chateau belt, Barbara Barbieri shoes, Rebecca Minkoff bag (all secondhand), Bozzolo tee (retail)

Thoughts: When it doubt, rainbow dress it up. Literally. We had a brunch date with friends and I didn’t know / couldn’t decide what to wear, so at the last minute I pulled this dress out of the closet and — bam! Outfit done.

Details: NBA jacket, Calvin Klein tee, Everlane pants, Gap belt, Converse sneakers (all secondhand)

Thoughts: OK, so this jacket was a total random impulse buy at VV. I don’t care about basketball or the NBA (unlike my son, who is obsessed) but something about this jacket spoke to me. I like the cut, the quilted effect, the floral pattern, and — above all — the weird juxtaposition of it all. I wore this on a library outing with the kids, and I have to say: I felt like A Cool Mom all the way 😉

Details: Gap dress, Only & Sons jacket, Aldo shoes, Rebecca Minkoff bag (all secondhand)

Thoughts: This outfit formula — boho dress, oversized denim jacket, chunky white loafers — feels trend-aware but true to myself. And that’s the sweet spot, isn’t it? It’s not about ignoring fashion, it’s about making it your own. And look, I know this isn’t the cutting edge of fashion by a country mile; the cognoscenti have already probably moved on from chunky shoes, and denim jackets. But these pieces allow me to update this dress in a way that, to me, feels fresh but also comfortable. And by that, I mean comfortable in my own skin, which is always my first and most important priority.

Details: LoveShackFancy top, Max & Co skirt, Donna Karan belt (all thrifted)

Thoughts: It’s been a hot minute since I found a designer label at the thrifts, so I had to pick up this LoveShackFancy blouse for its novelty, if nothing else. Well, that wasn’t the only reason, of course. I love the cotton candy colours; they’re sort of intense pastels, which I think are more flattering on me than traditional, soft pastels. I have to say, I am not especially impressed with the quality of this piece considering its retail price point (north of $350CAD) which is disappointing even if I only paid $7 for it. What the heck is happening with the fashion industry if this is what’s being sold as “designer” these days? Sigh. At least I have my vintage … including this skirt (old) and this belt (new). Can you believe I found this genuine snakeskin belt for less than $3? It’s probably from the 80s, and it’s superb quality that has held up beautifully over the years. I’m not sure anyone will be saying that about the blouse in 2050. (And no, don’t tell me my math is off. I refuse to hear it.)

Details: Suttles & Seawinds dress, Le Chateau belt (both Poshmark), tulle skirt (thrifted)

Thoughts: I love this dress a lot but wish it was slightly longer. Got my tulle skirt out. Problem solved 😉

Details: Ines de la Fressange x Uniqlo shirt, BR tie, Tahari jacket, CoH jeans, Brave belt, Ferragamo shoes (all thrifted)

Thoughts: I am still exploring the possibilities of this vintage Tahari jacket — the cut is so unusual and so good. I wanted to juxtapose the femme vibes of that cut with more masc styling. The glasses were an afterthought (I often forget I’m wearing my reading glasses, a sign of my age in more ways than one) but they certainly helped the overall Jenna Lyons-ness of the outfit. I wasn’t mad about it one bit.

Details: Vince top, Icone blazer, UO pants, Donna Karan belt (all thrifted)

Thoughts: This blazer is new-masquerading-as-vintage but I am a sucker for Grandma’s couch florals, so I got it. For this outfit, I leaned into the colour scheme, pairing the blazer with my olive-and-black striped knit top for a relatively subdued pattern mix moment. I decided to pick a light belt as a way to introduce some contrast and stop the black from taking over too much.

Details: Anthro jacket, Old Navy tee & sandals, vintage skirt, Coach bag (all secondhand)

Thoughts: I call this summer boho casual. Cotton layers, a floaty skirt (plus bike shorts), sandals. Easy and literally breezy. This particular skirt is a no-brainer choice when I’m stuck for ideas, because the pattern affords so many pairing options. For this outing, I decided to pick the maroon as a focal colour, and the outfit basically assembled itself from there.

Details: unbranded shirt (swap),Zara top, LL Bean belt, CoH jeans, Fluevog shoes, Rebecca Minkoff bag (all thrifted)

Thoughts: I got this plaid shirt at my last swap because I love its colours, but it feels a little bit disingenuous. I can’t say I have ever been a huge Guns ‘n Roses fan per se. Does this mean I’m flying false colours here? LOL! Anywhoo. The shirt is very oversized, so I choose a crop top to balance things out. I debated a bit over the choice of denim, but this ankle crop ultimately felt like the best option. Of all things, I think it’s the hat that ties it all together. This damn hat will end up being the MVP of my summer, just watch.

Details: Anthropologie dress, Lena Bernard necklace, Coach bag, Brixton hat, cowboy boots (all secondhand)

Thoughts: A simple outfit — you can’t get more simple than this — that is ALL about the accessories. I didn’t know how much I needed a black felt hat in my life until I thrifted this one. I was surprised by how wearable it is even on a warm day, which is great because it offers a nice alternative to my straw Panama hat. I like having different options to suit different aesthetics, and this one works better with the SW/prairie side of my closet compared with my other option. I am also surprised by how much I love this short dress/cowboy boot combo. Now that I have acquired a pair of (black) bike shorts, making it a proposition fraught with a lot less risk (of flashing), I see a lot of appeal in it. Too bad I only have 2 short summer dresses in my closet. Just imagine a flirty, swirly eyelet number! Something to think about, anyway. In the meantime, this dress never not gives 110%.

Details: Reitmans top, Lira jacket, vintage skirt, Dooney bag, Chie Mihara shoes (all secondhand)

Thoughts: I found this patchwork skirt at a garage sale, which is noteworthy insofar as (a) it’s fab! and (b) I never find clothes at garage sales! It is a teeny bit sheer, which is fine because — remember my bike shorts? Yeah, that was a good thrift purchase too. They’re another staple I never knew I needed and now can’t live without. Sometimes, it’s “boring” pieces like it that can make the biggest impact on your wardrobe, by unlocking the potential of other items or combinations. I might add this striped tank top to that list. I have a love-hate relationship with stripes; they’re so versatile — this top will go with so many things in my closet — but if they’re the wrong type, they make me sick. Literally. Thin stripes spaced too close together make me dizzy. This version? Works great.

Details: Tommy Hilfiger shirt, Fossil belt, H&M pants, Coach bag, Ferragamo shoes (all secondhand)

Thoughts: Vertical stripes, on the other hand, I can wear all day long. I love this men’s shirt so much; the navy, red, white and yellow combo is eye-catching but classic. This was a super basic outfit that punched above its effort level.

Details: Ralph Lauren shirt, Dries Van Noten skirt, tulle skirt, vintage belt, J. Crew shoes (all secondhand)

Thoughts: Speaking of stripes, this was my homage to Dries Van Noten upon news of his retirement from his eponymous label. As many of you know, DVN has been an inspiration to me for many years, and I treasure the pieces I own — including this skirt, which a dear friend gifted me years ago. It’s knee-length, which isn’t a style I enjoy wearing as much these days, but it’s too fabulous and precious for me to ever part with it. To make it fit the me of now, I layered it over my blue tulle skirt; the colours work together perfectly, and the skirts are compatible, size-wise as well. The DVN is loose enough to accommodate the extra layer, and the tulle skirt is not so voluminous as to be impossible to accommodate. Call it kismet.

Details: Zara dress, Jessie vest, Elizabeth & James vest, Manolo Blahnik shoes

Thoughts: Double the vest, double the fun? I would say so, wouldn’t you agree?