What’s Old Is New Again 😎

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Let’s talk about some styles we’re leaving behind in 2025. No judgement if you’re still rocking some of these in 2026. Confidence always beats trends.

The plaid flannel: I know most of you have one, and a few of you might be mad at me for this. But let’s agree to leave plaid shirts and shackets in 2025. 

Skinny anything: We may have overcorrected with the oversized baggy look, but skinny jeans and too-tight tailoring are rightfully staying in 2025. Opt for a slim or tailored cut if you like a more fitted look.

Flip flops: If boat shoes or loafers won’t suffice and you must show your toes, there are options. And flip flops aren’t it. 

Loud logos: I love a brand name as much as the next person, but a loud logo gets in the way of a nice outfit. 

Graphic tees: The exception is if you’re going to a concert or if you’re wearing a vintage tee as part of a throwback outfit.

In 2026, we’re leaning into a more relaxed fit and softer tones. Think wide-leg pants and cozy sweaters. Nothing looks deliberate, but everything is intentional.

Sweater polos: Finally, a good reason for me to recommend a men’s polo. You can’t wear this one on the golf course, but it’s great for work or date night.

Pleated pants: Yes and yes. Apparently, these Uniqlo pleated wide pants are selling out everywhere because of Timothée Chalamet’s latest role in Marty Supreme.

Relaxed fit: Pleated wide pants are part of a larger trend of loose, relaxed-fitting clothes. Some are calling it “soft tailoring” because fit still matters. Instead of bigger and boxier, look for flowing fabrics and intentional layering.

Soft colours: In addition to soft tailoring, stick with soft colours in 2026. You’ll be happy to hear that blacks, greys, and blues, are still staples, but softer colours like butter yellow, cream, and olive green are good ones to explore.

Manbags: You won’t escape this one. You’ll see all the cool guy celebs and athletes wearing some version of a manbag this year. Here’s a good starter bag if you’re into this trend.

The soft tailoring trend that’s predicted to take over 2026 is basically Fear of God’s whole aesthetic. You may know Fear of God for its Essentials sweatsuit, but I’m a fan because of its IG visuals, showcasing flowy, athleisure meets business formal, vibes. This perfect satin wool blazer offers a soft, looser fit that can be dressed down with jeans and a hoodie, or dressed up with pleated pants.

It’s not a coincidence that 80s/90s fashion increased in popularity among Gen Z around the same time Stranger Things released its new season in November. The trend (searches for “80s luxury” are up 225% on Pinterest) is defined by fleece and jean jackets, large graphic tees, chunky sneakers, and metal frame glasses. Stranger Things isn’t the only show bringing us back to nostalgic fashion. Bridgerton, back later this month, may or may not have influenced Christian Dior’s 2026 Men’s Spring collection, and Peaky Blinders is back in March, bringing with it a vintage 1920s style, centred around tweed, wool, and pinstripes. I’m predicting a lot of newsboy caps and pocketwatches at upcoming winter weddings.

Given the resurgence of the quarter zip, I’m giving you a few ways to spice up this business casual staple. Note: I skipped the obvious white round-neck t-shirt as an undershirt outfit. And, I’d avoid wearing the quarter zip on its own. It’s meant to be worn unzipped, and a bare neck with this specific piece will look unfinished. 

A wedding is not the only place to rock a tie. In outfit #1, the tie gives the dress shirt structure (keeps the collar in place) and creates a polished contrast to the beige shacket. 10/10

I’ve mentioned before that a dress shirt under a quarter zip should be avoided (the two collars compete with each other and look messy: Exhibit A.) Outfit #2 works because the dress shirt is untucked, and an extra button is unbuttoned at the top. This gives the shirt more room to stretch without bunching at the top, like this. See what I mean?

I’m sure you’re tempted to stick to a standard black quarter zip, but adding texture or a subtle pattern won’t hurt. Outfit #3 works because the pattern is the hero. The simple colours keep the outfit intentional and not flashy, and matching the sweater with dark pants keeps the outfit clean.

“What's the difference between Slim, Athletic, and Straight cut pants?” 

At many stores, you’ll also have to choose between Bootcut, Relaxed, Skinny, and Baggy! The best thing to do is to try on a few cuts, but when I’m shopping for a client, I think about these cuts in two buckets: fitted and relaxed.

Fitted

Slim, Skinny, and Straight cut pants fall into this category. As mentioned earlier in this letter, we’re staying away from Skinny anything, but if you like a more fitted look, Slim and Straight are good options. As the names suggest, these jeans fall straight down your legs, so they’re best for guys with slim legs and are better for low cut shoes.

Relaxed

Athletic, Bootcut, Relaxed, and Baggy are what to look for if you want a more relaxed fit. Bootcut has a bit of a flare at the bottom, made for boots. Relaxed fit are like Straight cut pants with more room throughout. If you have athletic thighs or a big booty, but you still want that slim fit look, try an Athletic cut. These should have more space in the hip and thigh area without looking loose. If it’s still not enough space, try buying a size up (enough to fit your legs nicely), then taking in the waist at a tailor.

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