Different stylists charge for their services in different ways; some have a menu of options to choose from. Sheffman prefers to charge by the hour ($200, but believe me, her time is worth it and she will have covered the whole market out there with her practiced eye on her own dime before she even crosses the threshold).

But here’s a hot (free) tip: Follow @ssheffman on Instagram for her editorial breakdowns of great examples of classic pieces. Recently she decoded the historical inspirations and new iterations of the tuxedo jacket, the fisherman’s sweater and the Fair Isle. She offers a range of the best options at every price point. It is like an old-style 90s magazine spread, with links!

So the in-person task could be just a closet purge. It could include her selling some of your better pieces by consignment on your behalf (because that is the legwork most of us just don’t do. As the meme goes, “Happy birthday to the pile of donation clothes on my chair!”). She could then organize your current outfits into new iterations. “Accessories are where the personality comes out,” she says of her approach to reworking what you have. Then, to fill in holes, she might take you shopping. Special occasion (ahem, mother of the bride, et alia) is a frequent request.

Where are the adult stores out there now? Sheffman is a fan of Andrews, and has had great success for clients there. She also likes Millie on Avenue Road and its range of sizing and options for the 50–plus demographic. And for mid-market hits? Sheffman suggest Banana Republic or J.Crew, both of which she says are “good again.” Even Mango can offer up seasonal hits.

But in general, Sheffman is not a fan of fast fashion. “It has a place. It can give you a quick hit of dopamine. But it is much more satisfying at this age to buy good quality things that are meant to last. And meant to be worn, not just take up space guiltily in your closet! We want to be lighter, freer, better edited! And fast fashion does not lend itself to that.”

Instead, she says, build that forever wardrobe, or clothing to empower you, as Sheffman also dubs it. “Being comfortable in your clothes is the number one most important thing.” That means, make sure they fit. Sheffman is an evangelist for alterations, and that can also be part of her customizable service should clients want her to do the fittings with the tailor.

You do, however, need to keep an eye on how silhouettes change. For instance, jeans and pants are wider now. That doesn’t mean you have to throw out every pair of skinny jeans but, she says, don’t keep more than one or two. “It takes awhile for the eye to adjust to new silhouettes,” she says. But that doesn’t mean you should follow trends slavishly at this age.

Shopping with a plan is key, and with a stylist it really can be a pleasure. “Clothing is expensive, you fear making mistakes and it is hard,” she says. First of all, she says, you don’t need something new for every wedding. Rewear, rewear, rewear. It’s chic.

As for forever basics, invest in blazers. They are back big time and they make you feel protected. A tux blazer, she says, a menswear blazer, a tweedy blazer are all good forever staples. “Merino or cashmere sweaters, turtlenecks,” she says. A white shirt, a blue shirt, a denim shirt, maybe a menswear stripe. Look to a denim wardrobe, in different shapes and tones. Invest in great trousers.

Shoes are complicated, of course. You need a sneaker wardrobe, Sheffman says, for practical sports pursuits but also for everyday. Plus you need a great white shoe, a vintage style. Ditto boots, which all have different purposes.

But the big category you need to flesh out here in Canada is your coat collection. Here Sheffman says her biggest outlays have paid off by lasting the test of time. But one trick she shares is to get a Uniqlo puffer vest, one of the thin ones that add an invisible layer, to make some of your fancier coats more versatile. Also, they can help out when big coats leave you too hot.

“Getting dressed is not optional,” says Sheffman. She says clients think she has a magic formula, but really it all comes down to playing around and shopping in your own closet, trying things to see if they work. Or, more importantly, to see if they make you feel good.

As she says: “Who is going to tell you its wrong?”

Always asking questions,

—Leanne Delap