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 😉

The title speaks for itself. I am turning 44 today, which feels like a weird, random number. It shouldn’t, because, since January, I’ve been telling people who ask about my age that I’m turning 44, so I’ve had a while to get used to the idea. Maybe my age will feel weird every year from now on, as the number continues to grow, further diverging from my inner state of mind. It’s not so much that, in my mind, I feel younger every year (relative to my actual age); it’s that I grow more and more ageless. I hasten to emphasize that I am very much speaking of a mental state of being; my body is feeling every one of its actual years. It is nice, that: feeling ageless. It’s a kind of freedom. From the time I was a young adult until I entered my 40s, there were a lot of “shoulds” tied to every milestone. Graduate from university at this age. Find a partner by that age. Get married. Buy a house. Start a family. The clock always tick, tick, ticking. It’s a generational thing, I know — the boomers’ legacy that Gen X never quite managed to shrug off (or maybe didn’t try hard enough to do so). Now, on the other side of 40, I’ve either run out of “shoulds” or stopped giving a sh*t about them or both, because I find myself unshackled from expectations. The clock continues to tick, but it is a countdown of time to explore the world and my place in it. To go where my curiosity takes me, to live according to the dictates of my own heart. Age has very little to do with any of it.

I’m so thankful that I had the opportunity to have my portrait done by Emilie Iggiotti recently because it made me think about how I want and enjoy to show up to the world in this moment of my life. About the clothes that help me to that, and the role they play in my life. About the things I wear for myself, and the things I wear for others, and the slowly disappearing line between them. With every year that passes, I feel that I owe less deference to other people’s expectations of me. I am only at the beginning of my Crone Season. I look forward to its apotheosis; the outfits will be magnificent.

This is me, now.

I’ve always been self-conscious about my teeth, so I trained myself to never show them when I smile. Talk about censoring oneself in service of societal standards of beauty. I am so glad I trusted myself in this moment, and trusted Emilie to capture it as beautifully as she did; when I was showing my best friend the gallery of images from the shoot, she picked this one as being the one that best captured my inner light. I think she was right. It shows the joy that I rarely let other people (except those closest to me) see. Maybe this is the year I change that.

Why not 44?