Always in Style: 7 Ways to Step Up Your Fashion Game at Any Age

A woman wearing a trench coat and white pants.

Photo: Clique Images/

One would think, given its inevitability, that aging would come with few surprises. But starting out with the first and most significant of these shockers — that it’s actually happening to you — getting older turns out to be a jumbo popcorn box of rude awakenings.

The latest, in my own case, being that despite having known exactly what I want to wear for the better part of five decades (and having amassed a rather significant array of options over the years), I now find myself frantically trying on and then rejecting outfits in a teetering pile on my closet floor like
a teenager.

What’s new are the small seeds of doubt: is this trying too hard or somehow inappropriate? And then nothing seems to look right, let alone fit like it used to, no matter how often you hit the gym.

“I don’t know what happens, but everything expands!” laments one friend, a former fashion buyer in her 60s who still manages to rock skinny jeans and a T-shirt. “I don’t understand how it’s possible. Did my bones move?”

What does happen, it’s agreed among my peers, is that after 50, somehow everything about you seems just a bit … off. “Suddenly nothing’s working,” notes my friend. “You don’t like your face, your body — not even your hair is right.”

In short, it’s like a second adolescence — and one just as driven by hormonal changes as the first time around. And even though we should know better by now, it can be hard not to succumb to hysteria, let alone envision a more grown-up version of you.

Unsurprisingly, given the lack of love in the culture for women over 50, the real underlying problem for most of us is overcoming a want of self-assurance. Sarah Collins is a Toronto-based personal shopper and image consultant. Says Collins, “Either you never were confident and now it’s time to get big-girl clothes, or you’ve lost your mojo and you need some help as to how to redirect traffic.”

One benefit of facing an identity crisis this time around is that we aren’t afraid to reach out for advice. With that in mind, here are a few tips for getting your mid-life fashion groove on — or back again.

A woman wearing a dark peach top, rolling her sleeves up.
Photo: Clique Images/

1. Clean Your Closet

We all make fashion mistakes. By this point in your life, it’s high time to say goodbye to anything that’s blocking your chi. And while you’re at it, take a good hard look at yourself in the mirror. “Ninety per cent of my clients stand in front of their closets and say, ‘I have a closet full of clothes and nothing to wear,’” says Collins. “It’s either too tight, too young or just outdated.”

For many, the solution may lie in the process of embarking on a little spring cleaning — getting rid of anything in your wardrobe that no longer, in the parlance of Japanese hyper-minimalist sensation Marie Kondo, “sparks joy” and stripping down to just a few great pieces that make you feel, despite the slings and arrows of this later-in-life adolescence, like you’ve still got it going on.

“I am seriously lean and mean now in my closet,” says one friend, a time-pressed yet always chic entrepreneur. “Anything that I haven’t worn in a couple of years, I just give away. It’s made getting dressed every morning so much easier to walk into my closet and actually be able to see what’s there.”

2. Find a New Guru

Life changes can throw you off balance so that even the goal posts have shifted. Maybe it’s time to stop kicking yourself for not looking like a 19-year-old runway model and start channelling someone more sophisticated.
“It’s time to embrace your inner Diane,” suggests veteran stylist Susie

Sheffman, referring to style icons Diane Sawyer, Diane Keaton and Diane von Furstenberg. “Diane Sawyer is always tailored, cool and classic; Diane Keaton has her own quirky, covered-up style; and DVF is the queen of Boho. There’s a Diane for every one of us, and all of them are inspiring.”

If neither Diane speaks to you, as one industry friend advises, “The internet is bursting with fashion leaders.” Or do as a former fashion editor friend did recently when she found herself uncharacteristically stumped in her search for a special occasion dress: search out a sales associate whose style catches your eye to help you navigate the racks. Nobody said you had to do this reinvention thing all on your own.

A woman wearing a pink scarf and grey sweater with her hand in the sweater's pocket.
Photo: Clique Images/

3. Buy Less but Better

Back in the day, you could rock something trendy and disposable so that it passed for designer duds. Now, not so much. The time has come to leave those fast fashion deals behind and dig a little deeper into your wallet. On the bright side, there is no better time than the present to start dressing like a grownup.

“It’s all about light, versatile layers of fine fabrics like cashmere and silk that are non-restrictive and give a great drape to the silhouette,” advises Sheffman, who believes in “honing in on what you really want to wear” and “buying smarter.”

A producer friend in her late 50s now feels justified in shelling out for what she calls investment pieces. “For me, that’s the blouse, jacket or jeans with a certain design element that stands out. I think of dressing as an artistic enterprise, a reflection of my personality. These pieces usually cost a bit more — but I also keep everything longer.”

Key items in my book are a terrific bag, statement coat and a swashbuckling boot that can take you anywhere — particularly when paired with a really good haircut (grooming at this juncture becoming ever more essential).

“I actually feel a bit liberated in my approach to dress now,” admits a fashionable friend who nonetheless eschews trends. “My wardrobe is pretty edited these days. I just keep it very simple and ever more focused on the lines that work for me.”

A woman wearing a grey top with a pink scarf and pink pants. The outfit completed with a brown shoe.
Photo: Clique Images/

4. Long, Lean and in Colour

Speaking of lines, consider the silhouette. More than ever, this is a balancing act: a fuller topper over pin-thin leggings, for instance, or a fitted jacket over palazzo pants, rather than baggy all around.

All-black may be slimming, but it also plays it a bit safe. Consider head-to-toe navy, elegant all-grey or camel as a more modern alternative. “The idea is to create a column of colour for a longer, leaner silhouette,” says Sheffman, who also recommends switching up that shorter skirt for something with more length.

“Don’t go for anything that cuts you across,” says Sheffman, who describes her strategy as “equal parts camouflage, coverage and creative.”

A woman wearing a trench coat and white pants.
Photo: Clique Images/

5. Accentuate The Positive

That being said, work with what you’ve got. Go out and invest in some new uplifting underwear — that same old bra you’ve been wearing for the last 20 years desperately needs to be retired. And if you’ve got it, feel free to flaunt it. Pretend you’re on a European beach and wear that bikini. If you’ve always liked your legs, there’s no good reason to hide them now.

“As far as what’s ‘appropriate,’ I honestly have no idea anymore,” says Toronto-based personal shopper Linton Drummond. “The bar keeps moving. Sixty looked very different 40 years ago.”

“On the bright side, I have boobs now,” says one friend who was flat-chested until her 50s. “So I’m having a lot of fun experimenting with tops and dresses with lower necklines, which is proving to be an excellent distraction.”

The reverse, of course, still applies. “My rule has always been the same,” says Drummond. ”Just don’t wear anything that looks bad on you.”

A woman wearing a thick necklace in peach, pale blue and black.
Photo: Clique Images/

6. Fun With Accessories

This is where you can really enjoy shopping again — particularly on your travels.

If you love turquoise or tartan, go ahead — start collecting! But please don’t wear it all at once; otherwise, you risk coming off like an amateur Iris Apfel.
Unchecked eccentricity carries with it a whiff of desperation. So go light on showstoppers like appliqué and metallics and remember: less is more.

“A great low-slung belt at the hip, a terrific necklace or dramatic pair of earrings, a killer shoe — all of these things are great — but choose your hero,” recommends Sheffman.

And perhaps keep it down to just one (all right, maybe two) heroes per outfit.

7. Smile for The Camera

As a family friend now well into her senior years once wisely told me, “Whatever your age, you are never going to look better than you do right now.”

If we’ve learned anything yet, it’s that life really is short.

Wasting it worrying about how you look at every stage seems extravagant to the point of profligacy. Ditto simply giving up or shying away from visually driven social media platforms such as Instagram (check out the account of Elon Musk’s stunning 70-year-old mother, Maye Musk, who has some 228,000 followers).

True, staying confident and engaged with fashion does get harder. But if every challenge comes with an opportunity, the hidden one here is surely the opportunity for greater self-awareness.

There’s no better time than the present to fully embrace and enjoy being the person you’re becoming.

So go ahead and strike a pose: there’s nothing that looks better on you — at any age — than a smile.