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Courtney Shea posed the question to five fashionable Canadians and heard a common response:When it comes to self-expression, time is on everyone’s side

Laila Oestreicher

Age: 29, Occupation: Interior designer at Thom Filicia, New York

“My style has changed a lot since my early 20s. Back then, it was Chuck Taylors, a neon shirt, ripped jeans, lots of scarves. I was definitely influenced by the musicians I was listening to at the time – David Bowie, Debbie Harry, Karen O. I spent a lot of my twenties dressing in a way that I now think of as ‘playing dress-up,’ but I don’t regret it – not even the blue eyeliner.

Your 20s are for making mistakes and your 30s are for learning from them.

I remember when I got my first part-time job in high school and had that first disposable income. I went nuts at H&M and really had fun with cheap and cheerful fashion. Now I’ve realized that the shirt that cost $12 doesn’t make it through the wash, so it’s really a waste of money. It pains me to admit, but I’m realizing that my mother was right all along: The less you have on, the more things shine, assuming those items are good quality. Now I’m buying for the long term rather than buying something for Saturday night. I like Vince and Theory. They do basic silhouettes that really work. In terms of clothing, I’m not really a colour person, which is sort of a design-industry standard. You want to look current and stylish, but you definitely don’t want to scare away clients. I try to avoid making any kind of statement. Subtlety goes a long way.

I’m quite a bit loser in terms of my taste in decor. My home is still largely a mix of hand-me-downs from my parents and IKEA, but I have started to collect some amazing items. My prized possessions at the moment are my Florence Knoll berry-coloured mohair club chairs that I found in Williamsburg a few years ago.

The edges are worn out and there are holes in them, but they are an original design classic – and I found them for nothing!”

Mo Handahu

Age: 37, Occupation: Fashion blogger, Halifax

“When I was younger, I had a much more athletic body type. It wasn’t until my mid– to late 20s that I started to put on weight. But I have so much more confidence now as a plus-sized woman than when I was smaller.

I think in your 20s, you tend to be very concerned with fitting in. I was always following the trends and would never want to be seen wearing something that was ‘out.’ I shopped at Le Château like all the rest of my friends.

At 37, I feel totally comfortable embracing the things I like, whether they’re on trend or not. Most of my wardrobe comes from vintage shops. One of my current favourites is a jacket I found at Value Village with llamas on it. My younger self would have thought it was way too out there.

It’s been a similar evolution in terms of my beauty regimen. As a young girl, you tend to follow the rules. I was never a fan of eye shadow, but I wore it all through my twenties because it’s what most of my friends wore. Now, I’m strictly a mascara girl. I also used to relax and perm my hair, which was a lot of upkeep. Part of that was wanting to fit in, but also, there just weren’t a lot of role models for women of colour.

The internet has really changed everything.

I love my hair now. I recently died it purple, which is definitely not something I would have done 10 years ago.

I guess, if I could tell my younger self anything it would be to not worry so much about what everyone else is doing. Also, to hold onto those 90s blazers and palazzo pants. Everything comes back if you wait long enough.”

Colette van den Thillart

Age: 47, Occupation: Creative director at Nicky Haslam Design, London

“I don’t know if it’s something you learn or something you just succumb to, but I’m definitely guilty of valuing comfortable clothing more and more as I get older. I don’t think you have to sacrifice style for comfort. At this point, I prefer those things that are less obvious.

Herve Leger and that whole body conscious look – that can look great on people in their 20s, and there are certainly women my age who can pull it off. But just because you can doesn’t mean you should. I’ve never had the desire to look younger than I am.

A 20-year-old is a wonderful thing, but I’m more excited about advanced style, and the liberation that comes with age. My style icon is Auntie Mame as opposed to a 22-year-old pop star.

I’m going through a major caftan stage right now. I think I have at least a dozen.

Some are authentic from Japan, some are vintage, some are brand new. I’ll wear them with shorts and slippers or with heels and a big belt to something more fancy. There really is a caftan for every mood. You know when you’re in your pyjamas, just schlepping around the house? Throw a caftan on and all of a sudden you’re a movie star.

Over the course of my 40s, my taste in design has become a lot more personal and a lot more daring. I burnt plywood to put on the floors of my foyer. I don’t know if I would have had the guts to do that when I was younger. And as a designer, it tends to be more fun working with clients in their 40s, 50s and older. The 30-yearolds want to know what everyone else is doing. They’re worried about what their friends will think. The 50-year-olds – they’re over it.”

Marie Khouri

Age: 55, Occupation: Sculptor, Vancouver

“I laugh when I think of the number of things that I bought in my 20s and 30s just because somebody at the store said they looked nice. And then they stayed in the closet. At 55, I don’t want anybody else’s opinion. I have very close female friends, but when I go shopping, I go by myself.

In my 40s, I took a sabbatical from software development for the financial markets and began developing my career as a sculptor and becoming the person I am today. Once I became successful in my career and financially independent, I didn’t need to take half an hour to get dressed. I take five minutes now, and I wear very little makeup.

I’ve been wearing all black for the past 10 years. Part of it is about placing the focus on my work. When I was younger, it was me who needed to be in the foreground; now, that has totally changed. My work is how I express myself. Also, black is the easiest thing to pack. I can basically go for 10 days with a carry-on. You take two pairs of pants and three shirts and just mix and match.

Before moving to B.C. almost a decade ago, I lived in Paris for 25 years and living there gave me an appreciation for having fewer, quality items. I would rather have 10 exquisite pieces in my wardrobe than a hundred. I don’t like anything with branding. I don’t want to be used as a billboard.

Learning to love yourself is wisdom that you acquire with age. It’s what helps us face our wrinkles and all of the other things that life throws at us.

When I look back at pictures I can’t believe how much I was hiding behind all of that makeup.

Today I feel that style is holistic. It’s not my clothing, my hair, my body – it’s all just me.

I do still dye my hair. My goal as I get older is to let that go and live my age as truthfully and serenely as possible.”

Judith Maria Bradley

Age, 70, Occupation: Fashion Model, Toronto

“I didn’t start my professional modeling career until two years ago, at 68. Just wild! I never liked my picture being taken. That’s what often happens in life: When we aim for something, the opposite happens.

One of the things I’ve learned is that style is so much more than what we wear. Style is in the spirit of the person. It’s our politics, the amount of clothing we have in the world, what we hold dear and what we don’t.

I suppose it was my mother who first told me that you have to be sure to look presentable when you go out because the whole world has to look at you. She made my clothes by hand and she always maintained that quality was better than quantity, which is another thing that has stuck with me.

I don’t understand this fascination that people have with disposable fashion. Clothing should be special.

The first Blue Jays game I ever went to was back when baseball first came to Toronto in the 1970s. I wore this gorgeous red Valentino gown. This one lady finally turned to me and asked, ‘Why are you wearing that?’ She was in a tracksuit or whatever. I looked at her and said, ‘But, darling – why are you wearing pyjamas?’ It’s habit. It’s convenience.

People are so busy today, they have no time for anything. The bombs could be falling and I would still do yoga. I’ve done yoga twice a day for 50 years. I still have great legs. I will wear a short skirt with a flat shoe, but never with heels. When you’re my age, you don’t want the world to be your gynecologist.

I don’t hold onto my clothing anymore. I remember a point in my life when I had four closets.

Now I’m down to a more basic wardrobe. I love to give things away. If someone comments on loving a scarf I’m wearing, I’ll give it to them. I did keep the red Valentino gown, though.”

Share your age-defining style (and selfies) on Instagram and Twitter, and tag your posts @globestyle and #ownyourage.

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