We Should Do This Every Year 🗓️

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These are my picks for the people, pieces, and trends that stood out in 2025, along with a few lessons learned from recommending and buying clothes all year long.

Best-Dressed Celebrity of the Year

Colman Domingo for impeccable tailoring and bold looks that don’t cross into theatrical, and Pedro Pascal for mixing classic tailoring with modern pieces like sleeveless vests and oversized pants.

Best-Dressed Athlete of the Year

It’s hard not to mention SGA, our Canadian star, but I have to give credit to LeBron James’ cool, “I woke up like this” style, and Lewis Hamilton for giving us a little more drama. 

Best Accessory of the Year

Though not yet embraced by the mainstream, celebrities, athletes, and style makers have made the man bag the most notable accessory of 2025. 

Best Style Trend That Will Carry into 2026

Monochrome, and not just in navy and beige. This year, burgundy was the stand-out monochrome palette. Next year, try forest green or shades of red.

Best Bang for Your Buck

I should get a sales commission at this point for the number of Banana Republic cashmere sweaters I’ve recommended to my clients. It’s not the cheapest one on the market, but for the quality, colour options, and fit, it’s my favourite investment of the year.

Best Wallet-Friendly Brand 

I’m always surprised when someone tells me they’ve never shopped at RW&Co. If you’re one of those people, I highly recommend checking them out in 2026. They’re a step up from Zara and not as pricey as Banana Republic. They have great business casual styles that won’t shrink the first time you put them in the wash. 

Best Jacket for a Canadian Winter 

This one’s a splurge, for sure, but it’ll get you through many winters, and you can take it skiing or to dinner. Plus, Mackage is a Canadian brand. 

Retailer Fumble of the Year

Speaking of Canadian brands, Montreal ecommerce company SSENSE filed for bankruptcy protection this year after being valued at one point at $5 billion CAD. 

Best White T-Shirt 

I’ve tested a bunch of the favourites, yes, even the ones at Uniqlo, but I keep going back to this knit t-shirt from Zara. The fabric isn’t stiff like a lot of t-shirts, making it really easy to tuck into pants and wear under jackets. 

Best Peacoat for Style and Function 

At first glance, this Reigning Champ peacoat looks like any other peacoat. Look closer, and you’ll notice oversized shoulders and a boxy fit. This gives dimension and length. The style says, ‘I’m business casual, but I know the rules well enough to bend them.’

Best Brand I Slept On Until 2025 

Reigning Champ was a close contender for this one, but the brand I wish I’d discovered sooner is Kith. They’re known for their celebrity and brand collabs, but I’m here for their outerwear and unique prints.

Simplest Style Habit With the Biggest Payoff 

Everyone’s body is different, and you’re likely never going to find a brand that fits you perfectly. Get yourself a tailor (your dry cleaner can probably do this) who can make common alterations like pant and sleeve length. And next time you’re struggling to find pants that fit your thicker thighs, buy a size up and get the waist taken in. 

Retail Reality Check of the Year

There are so many American brands I have yet to explore because of the reality of tariffs. Most of the brands I recommend these days are Canadian or have a Canadian retail presence. Good for Canadian brands, bad for people looking to expand their style in 2026. 

Closet Wake-Up Call of the Year

Turns out, Zoom couldn’t protect us forever. Companies mandating work-from-the-office policies made headlines at the beginning of the year. Now, it seems most companies are asking employees to head back to the office full-time. The silver lining? A lot of closets are finally getting the attention they deserve.

Since most readers of this newsletter are men, I thought I’d share a few last-minute gift ideas for the wives, daughters, sisters, moms, and other special women in your life. With just two days to go, delivery is probably out of the question, but you can grab all of these at the mall.

Jo Malone candle - Not your average candle. It’s an IYKYK kind of gift - and it shows you know. 

Lululemon half-zip - Most of the time, I’d avoid gifting clothes, but you can’t really go wrong with this coveted half-zip.

Drunk Elephant skincare - You can find gift sets at Sephora or HomeSense. If she already has an ironclad skincare routine that doesn’t include Drunk Elephant, no one ever says no to a nice body lotion.

YSL Loveshine lip oil stick - It may be hard to choose a colour, but these go on pretty sheer. Or, if you can steal her favourite lipstick for a day, the sales reps at Sephora can help you find a similar shade. That it’s YSL in its distinct tube will make the difference. 

Matching sweatsuit set from Aritzia - Nope, you can’t have too many matching sweatsuit sets. But maybe choose a colour she doesn’t already have. 

Ember mug - Everyone I know who has one raves about it. This is an especially good gift for moms who can’t finish their coffee in one sitting. 

A Kobo or Kindle - Perfect for travel, or for those times when hauling a full hardcover is just too much.

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