The fall outfit that works anywhere 🍂

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It seems like only a few years ago when everyone was obsessed with getting the latest smartwatch. But last year, for the first time, smartwatch sales declined. Tech and market factors played a role, sure, but is it a coincidence that I’ve seen more men wearing classic wristwatches, and have been getting more client requests to find a good one? I think not. Here’s a list of 12 I like that won’t break the bank. Number 11 - the rectangle face - is my favourite right now. On a similar note, with cellphone bans rolling out in elementary and high schools across Canada, teenagers are rediscovering Timex, Casio, and Shark watches. Give it time, and millennials will pick up on that trend, too.

Return to office, but make it stylish. There's a reason most of my clients ask for an update to their business casual wardrobes. With more companies moving back to in-person work, the good news is that office style has evolved beyond the stiff dress shirt and tie. The go-to look is now a polo with dress pants, and the most “formal” is a dress shirt with dress pants. If you want to elevate your office outfits without going too far, start small: skip the belt and tuck in your shirt, swap the predictable navy blazer for something with a subtle pattern (I recommend this one a lot), or stick to what feels comfortable but go all-in on a monochrome palette (see below).

I talk about monochrome outfits a lot. Monochrome means one colour, so in practice, it’s pairing a top and bottom in the same shade family. Shoes and accessories can be different. You can try it with any colour, though navy blue and cream work best. The goal isn’t to match exact tones, but to keep shades in the same family. A good rule of thumb is to mix in texture: a wool sweater or shirt underneath a matching suit adds depth without breaking the palette.

Not surprisingly, fall fashion is all about neutrals. But this season, greys and browns are taking centre stage. Good thing your closet is not just black, white, and blue, right? Even if it is, these colours are easy add-ons whether your wardrobe is minimalist or colourful. RW&Co has nice rich browns (love this coat), and a grey overcoat is a nice addition to any closet.

Kith is a New York brand that’s definitely on the pricier side. They have a store in Toronto in Yorkville if you want to check it out in person. They’re known for their brand name and celebrity partnerships, but what I’m loving this season is their outerwear. A guy on my flight was wearing this jacket, and I can confirm that it’s even nicer in real life. 

We’re nearing the end of another major run of fashion weeks in NYC, London, Milan, and Paris (ongoing until next week), previewing Spring/Summer 2026 lines. I won’t try to condense all the highlights in one short paragraph, and instead will spotlight a few brands with standout ready-to-wear pieces. 

This week, check out SIVAN, by Brooklyn designer Jack Sivan. He launched in 2020 with bespoke tailored menswear and has since expanded into ready-to-wear collections, all rooted in sharp tailoring, which, in my opinion, is half the battle of any good outfit. What I love about his Spring/Summer 2026 collection is the focus on inclusivity, with designs made for men of all shapes, sizes, and abilities.

The downside of SIVAN is that it’s not easy to buy. They have a few pre-sale items available on their website, and you contact them for bespoke tailoring, but that’s all for now. I’d still keep this one bookmarked. With the brand’s recent runway success, my guess is production will ramp up soon.

Canadian brand Unbound has some of its popular merino tops and pants on sale.

Simons’ house brand Le31 is on sale. This is a nice quarter zip.

Here are all the browns and greys on sale at RW&Co, including this amazing double-breasted blazer (not a lot of sizes left).

“What’s a bulletproof outfit I can wear from work to the Blue Jays game to the bar without looking too out of place in each setting?”

The goal here is balance. You want an outfit that’s stylish but not trendy (good for work), casual but not sloppy (good for the game), and comfortable enough to last all day (and into the night). 

Since it’s fall, think layers. A coat is a must, but steer clear of trenches or peacoats; they’ll be a hassle to deal with at the baseball game. Same goes for dress shirts or dress shoes, which can feel stiff and get uncomfortable throughout the day.

Try this formula: Top: light sweater or textured/wool t-shirt, Coat: casual bomber-type; skip the trench coat or peacoat, Bottoms: trousers or chinos, Shoes: clean sneakers or loafers. 

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