What to Wear Over 50 (Without Looking Frumpy)
Real style tips from the Three Wild Women who’ve been there, styled that!
Hi there—it’s Helen here, and if you’ve ever stood in front of your closet wondering if something is “too young,” “too old,” or just plain wrong for your age, trust me… you’re not alone. I hear this in the shop ALL. THE. TIME. Especially this summer when we had this beautiful Orientique Australia dress that everyone kept saying, “looked too young.” or…
“Is this okay for someone my age to wear?”
“I’m not sure if I can pull this off.”
“I just don’t know if it’s age appropriate.”
Let’s set the record straight: Style doesn’t come with an expiration date. And the only “rule” that matters is whether you feel good in it.
Still, it helps to have some guidance. So Skippy, Leslie and I are sharing our go-to pieces and real-life style tips that prove you can look modern, pulled together—and completely yourself—at any age.
Let’s dive in.
Ditch the Frump—Not the Comfort
Helen: Listen, I’m not here to give up comfort. I’ve earned my elastic waistbands and popcorn eating tunics. But there’s a difference between “comfortable” and “frumpy.” For example, the Oh My Gauze Pant and Top are flowy and soft without swallowing you whole. I wear the white set with a statement necklace and feel like a million bucks—easy, breezy, and nowhere near boring. For me, it’s about how it gets pulled together that ditches the frump without the comfort.
Skippy: I used to think wide-leg pants made me look shorter, but these ones actually balance out my shape. I even got talked into the lilac colour (yes, me!) and I’ve worn them three times this week. They don’t wrinkle, they feel like air, and no one would call them frumpy. For me, it’s about making sure that things are tailored to me - because I’ve got these damned Olive Oil legs I’ll get pants taken in on the sides to have them fit me better.
Swap “Shapeless” for “Intentional”
Leslie: A lot of women over 50 fall into the oversized trap and there’s nothing wrong with oversized, the trick is structure. The Joseph Ribkoff Pant gives a clean line and a little stretch, and the Joseph Ribkoff Top drapes on purpose—not by accident. I love the layered detail because it does all the accessorizing for me… Not that I’m going to give up accessories.
Helen: Right? And it skims, not clings. You want a piece that knows what it’s doing.
Use Colour to Wake Up Your Closet
Skippy: Okay. Everyone sit down. I’m about to recommend colour. The Lea & Luc Top in blue is now in my wardrobe—and I don’t even miss black. It’s soft, modern, and doesn’t scream “trying too hard.” I wore it to brunch and three people asked me where I got it. I have grown to like it but it really was trusting that I knew what colours looked good on me. I think I always knew but it just took a little more trusting myself.
Leslie: I love the Lea & Luc Blouse layered under a denim jacket. It’s artsy without being loud. The print gives you interest, but the shape is relaxed. So if you’re new to colour or pattern, this is a great entry point. Again - not frumpy because we’re using print to add some focal point and layers to pull it together. It’s totally about having it be a choice rather than just something you throw on because it’s clean.
Helen: I’ve always said, once you find your colour, lean into it. You don’t need the whole rainbow. Just one or two that make you feel alive.
Add a Third Piece (This One’s Magic)
Leslie: Want to feel instantly stylish? Add a third piece. Not a whole new outfit—just one topper that pulls it together. A jean jacket, an open blouse, or even a bold necklace can do it. It shows you thought about your look, even if you got dressed in five minutes.
Skippy: I throw on the Joseph Ribkoff sparkle jacket when I need to go from errands to drinks. It’s comfy, sparkly in a grown-up way. Now, I know Helen is going to say it’s a little out there but why not wear the fun sparkle jacket? I have it in my closet - what am I waiting for? But that first time picking out your produce in a “fancy” jacket you’ll get some looks but you also get a bunch of people saying how great you look.
Helen: And if you’re still running hot like me, opt for breathable layers. We stock plenty of cotton and gauze toppers that won’t make you sweat.
Dress for You, Not a Number
Helen: Your age doesn’t define your outfit. You do. Whether you’ve always been a pants person, a dress devotee, or someone who only shops when her favourite shoes wear out—we’re here to help you build a wardrobe that works for your life.
Skippy: Style isn’t about trends. It’s about feeling like yourself when you walk into a room.
Leslie: And if you don’t know what that style is yet, come in. We’ll figure it out together.
So there you have it. Real advice from three women in their 50s, 60s, and 70s who have seen a lot of fashion trends—and aren’t afraid to bend the rules.
Frumpy? Not on our watch.
Come visit us in Westboro or check out our latest finds online at threewildwomen.ca. We’ll help you dress in a way that feels like you—only better.
Style doesn’t end at 50. That’s when it gets interesting.