I rang Talia Brown Thall, a stylist who always has the best practical advice. Brown Thall has worked with celebrities, from Meghan Markle to most recently Avril Lavigne, whom she outfitted for her last concert tour. But it is actually her work as a personal shopper for us regular folks that gives Brown Thall such range and sage opinions.

First thing she said to me when I had explained our topic for this week was about pants, the most common error in aging male style. “Wear pants under the belly, instead of around the belly!” she says. “Also, you are going to have to try on more styles and brands than you are used to. As men get older, their tushies disappear.” Baggy seats, she says, are a clear sign of giving up on yourself. 

For a guide on fit, look to centre your back pocket. “Right in the middle of your tush.” As Brown Thall says, she, like many of us, has a soft spot for the Dad Bod. You guys are lucky! Still, she recommends an old-fashioned fix for lining your shirt (see above: moobs). “Wear an undershirt! It could be a classic white beater, but you might be more comfortable with a thick cotton T-shirt that fits you really well. If you get the right one, it holds you all in. It’s like Spanx for men!” She recommends Calvin Klein undershirts and also the old standby, Hanes.

As for the tucked in/untucked shirt debate, that generational divide seems to be disappearing. If you like your shirt tucked in, crisp and tidy is good! If you like it out, it won’t make you look older or younger any longer. But most importantly, says Brown Thall, it has to fit. “Just get a custom shirt. It has to hit at the right length if you want to wear it out. It is very frumpy if it is too wide or too long, if the shoulders fit in the wrong spot, that can add weight. Make sure your neck and shoulders are your size!”

If custom is not in your wheelhouse (custom shirts start around $200), then go for alterations. Take in the waist, fix the length. But Brown Thall suggests you try one custom shirt and see how it changes how you feel. I support this project 100 per cent. Custom shirts are what I give my own husband for special occasions. They last forever. The fabric is so much better. The workmanship is impeccable. We agree also on a few sources for you to tap into. We are both a fan of Marlon Durrant, purveyor to both Bay Street and basketball royalty, who has an atelier on Avenue Road in Toronto. 

Brown Thall also suggests Davide Afnani in the west end of Toronto and Sydney’s on Queen Street West. But shirtmakers in every town and city across the country will make a better shirt for you than you will find on any rack.

Jeans, says Brown Thall, also need to be altered. “Take in the waist if there is a gap,” she says, “don’t just cinch it up with a belt. That will affect the tushie, yet again,” she says. And even though stretch fabric is terribly tempting, it doesn’t have the crisp look men need to polish their look. “Plus stiff cotton denim, like a classic Levi’s 501, will hold you in more, make you stand up straighter,” she says. “Stretch fabric stretches out, and looks sloppy.”

Length of pants is another important thing to consider for your total silhouette. Brown Thall prefers men’s pants to fall right to the cape of the heel, which is the end of the heel. “Straight leg is the best option,” she says, the most flattering. 

“Keep it as neat as possible, and clean and fit as well as possible.” 

In general, as you age, now is the time to invest in the best fabrics, says Brown Thall. They drape and fall on the body with creases in the right place, not in an awkward or unattractive place. “Get a good tweed pant. Silk-lined tweed will fit better and last longer because they wear better.” 

For other brands that Brown Thall suggests you look at, don’t sleep on Club Monaco (“Great cashmere”) or Banana Republic, which is working hard on making its assortment sophisticated and suitable for the 50-plus demographic. Harry Rosen and Holt Renfew, she adds, both offer customization and alteration. And Mark’s Work Wearhouse is a favourite source of hers to go shopping with male clients for jeans and flannels. She is a fan of retailers GotStyle and Over the Rainbow for jeans, especially in person as the sales people at these shops are extra sharp at matching clients with the right pieces. And beyond Levi’s, she recommends looking at Seven for All Mankind and Citizens for Humanity for a sophisticated and elegant jeans fit for men.

As for necklines, the thing that makes a double chin look best is a properly fit shirt or sweater. “Your body keeps changing, so your clothes have to keep changing. That doesn’t mean you need to throw everything out and start over,” she says. “But every season you need to go through your clothes, and alter things as you go. If buttons pop, or the neck doesn’t fit? Get rid of it.” 

Always asking questions,

—Leanne Delap