Dress to express: Five Canadian women on finding their style in midlife | Canada Voices

There was a time, not so long ago, when society’s message to women over 40 was clear: recede and do it gracefully. Dress “for your age.” Stop taking up space.

But that’s changing, one closet at a time. Scroll through social media and you’ll find a growing wave of women in their 40s, 50s and beyond refusing to be invisible and building devoted followings in the process.

We chatted with five Canadian content creators about how their sense of style has evolved with age. From Surrey to Quebec City, they tell The Globe how getting dressed in midlife has become less trend-focused and more personal, and what they want other women to know about rediscovering their own style.

Michelle Osbourne, age 51, Quebec City, Que.

IG: @itsmichelleoutloud

“I just started feeling like I had nothing to prove anymore.”

My current style in three words: Minimalist. Comfortable. Ever-changing.

The mid-life style evolution: For most of my life, I hated myself so much that I didn’t take a single photo. I had no adult pictures of myself until I turned 40 and finally booked a shoot, just me and a rack of clothes I loved. That was the start of feeling free. Then COVID lockdowns hit, and I found myself on TikTok in red lipstick, half-dressed, dancing, wanting to prove a point about my body after years of hiding it.

Connecting with so many women online was empowering, even if I look back now and see how performative it was. As I got more comfortable in myself, I stopped needing the makeup, the perfect outfit, the proof I was allowed to take up space. I let my style follow how I actually feel instead.

The lesson I learned from making my style personal: I used to dress to prove something: tight dresses, two hours of makeup, the whole performance. Then I stripped it all back and realized I felt more like myself with less. Now I go for what flatters my spirit over what flatters my body. There will always be people telling you what’s in, what’s out, what you shouldn’t wear. I don’t want to reach my deathbed having dressed for anyone but me.

Dr. Mary Marquardt, 59, Ottawa, Ont.

IG: @thechicacademic

“Take the risks you’ve been putting off.”

My current style in three words: Modern. Polished. Edgy.

The midlife style evolution: It took me until my 50s to fully embrace my personal style, and in many ways, to give myself permission to be seen. I’ve spent my career as a neuropsychologist in a hospital, and for years I dressed the way professional women are expected to: in suits, conservatively.

I loved fashion and being creative, but I kept that side of myself separate, worried about what colleagues or patients might think. Starting my lifestyle and fashion account in my 50s changed that. I “came out” as a fashion lover and a doctor, and stopped feeling like I needed to compartmentalize different parts of myself.

The lesson I learned from embracing my whole self in my style: Show up as authentically as you can. We live in a culture that prizes youth and holds women to relentless beauty standards, while placing far less value on aging well and becoming more fully ourselves. There’s power in seeing women over 50 who are creative, stylish, visible and still evolving. To me, true style is confidence: wearing what you love, trusting yourself, taking up space.

Christin Bryant, 54, Edmonton, Alta.

IG: @cbstyled

“Confidence is 99 per cent of nailing an outfit.”

My current style in three words: Casual. Polished. Classic.

The midlife style evolution: In my 20s, I wanted to follow trends and blend in. Later, raising kids meant getting down on the floor or into paint, so practicality was important. As I got older, I no longer wanted to dress for others, and with more time, I could play around with different outfit combinations. Getting dressed became a way to explore and express my personality.

Sharing my process on social media, then hearing back from people, has become its own kind of confidence loop. You try something, someone tells you they love it, and you think, “Okay, I’m going to keep going.” That feedback taught me things about myself I wouldn’t have found alone.

The lesson I learned from inviting community into my style: Stop being your own worst critic. The flaw you’re fixating on, nobody else even sees it, so wear the thing anyway – like you mean it. That’s what I wish more women my age would just let themselves do.

Shannon Mann, 50, Surrey, BC

IG: @shannonmannofficial

“Getting dressed well is a kind of self-care, and I’ve stopped apologizing for that.”

My current style in three words: Chic. Elegant. Expressive.

The midlife style evolution: I’ve always been polished, even managing the watch counter at Birks as a teenager. But somewhere in midlife, my thinking shifted. I became very conscious of my mortality, of how many good, healthy years I actually have. I don’t know how many more hydrangea seasons I’ll get to see while I’m well, so I’ve stopped waiting.

I think about the lives my grandmother and mother had, and how markedly different mine is: the freedom, the independence, the choice in how I express myself. As a proud Punjabi woman, I love getting glammed up in a full Indian outfit as much as I love a great blazer. Fashion has always made me feel good, and now I treat getting dressed as seizing the day, rather than something to get to later.

The lesson I learned from embracing my body in my style: Own the body that’s gotten you this far. We compare ourselves to filtered images and forget what’s real. So what if your ankles are a little swollen, or you’ve got a few varicose veins from years of wear and tear? You still have to treat yourself with that same love. It’s a gift to be in the body you’re in.

Chantal Sarkisian, 42, Clarence-Rockland, Ont.

IG: @chantsy

“I stopped asking if an outfit was age-appropriate and started asking if it felt like me.”

My current style in three words: Comfort. Feminine. Edgy.

The midlife style evolution: As I’ve gotten older, my body has naturally changed, and my relationship to getting dressed has changed with it. There was a period where I’d put something on and feel like I was cosplaying, like I was trying to squeeze into a younger version of myself. At some point I decided to stop caring whether an outfit was “age-appropriate” and start asking whether it felt like me.

Now I enjoy what is called “dopamine dressing.” If you open my closet, it’s full of colour because the right bright dress lifts my whole mood. My style comes down to three things: comfort, something feminine like a bow or a skirt, and what I call hard—an edgier piece that adds structure, like a leather bag with boots. When I tap into all three, I feel most like myself.

The lesson I learned from making room for my present-day self in my style: Fill your cup first. I see so many women holding down a job, a family, a home, and not being seen for it. Taking time for yourself isn’t selfish; it’s necessary. When you set an intention for yourself, whether it’s how you dress or how you live, everything you do gets you closer to it.

Five tips for finding your style in midlife

Get your colours done

Your colouring shifts over time – from your hair colour to your skin tone – so the palette that suited you 10 or 20 years ago may not be the one that lights you up now. A fresh colour analysis cuts the guesswork fast.

When in doubt, take it to the fitting room

You can’t tell what a piece will do for you until it’s on. Grab it in a couple of sizes and see how you feel in it. The surprises are half the fun.

The number on the tag is nobody’s business but yours

Sizing runs wildly different from label to label, and you’re the only one who sees it. Buy the size that fits and feels good. Don’t let two digits talk you out of something you love.

Comfort isn’t the consolation prize

The most stylish woman in the room is rarely the one suffering for her outfit. She’s the one in the look so effortless she practically forgot she was wearing it.

No one is watching as closely as you think

The flaw you’re fixating on is invisible to everyone else. Wear it like you mean it – how you carry a piece ultimately outshines the piece itself.