Men’s Guide to Fall Fashion: Transitioning from Summer in Style

Sorry to say it gents, summer has come to a close. Sure, maybe you won’t be able to spend all day at the beach, but it’s time for the other pleasures in life: scenic hikes, backyard bonfires, hot toddies, Thanksgiving, and the NBA-slash-NFL-slash-CFL-slash-NHL-slash-World Series starting.

There’s a lot to look forward to, but entering into the transitional shoulder season means the weather can be a bit touchy. Sun in the morning, cool rain in the afternoon, tepid drive home, frigid evening. And that’s just one of the various options that can come out of Dr. Strange’s alternative weather universes.

To help you guys survive transitioning from summer to fall in style, we’ve built out a list of the essential items you need as the temperatures begin to dip.

Transitional Weather Essentials for Guys

Eco-Friendly Hoodie

If you’re still holding onto the glory of the summer sun, pair your favourite shorts with Tip Top’s sustainable long-sleeve hoodie. Made from eco-friendly organic cotton, enter into the cooler months with a clear conscience - and with your body temperature intact.

Quilted Vest

As the season persists, an extra layer of insulation becomes dire. But you also don’t want to overheat. When we come to terms with the weather reality, we like to throw on Projek Raw’s quilted vest. Perfect over a hoodie, a plaid flannel shirt, or with a casual dress shirt and tie.

Flannel Shirts

Speaking of flannel shirts, there’s a reason why Canadians love them so much - they’re so darn warm and good-looking. Like a soft hug, if you’re digging for a healthy dose of tradition, try a plaid shirt from Projek Raw.

We also give a big co-sign to Daniel Hechter Paris’ Jaspé Flannel Sport Shirt - just as soft and warm, but without the plaid pattern.

Transitional Suits

If you didn’t notice, the common theme here is flexible layering. Add another light layer when you’re cold, remove a layer when you’re warm. Suits are a great place for layering - especially if you’re going somewhere more formal.

By wearing a 3-piece suit, you’re giving yourself a TON of wiggle room. Take this classic (and clever) slim-fit check suit from G Grafton. With a peak lapel, tartan check, and robust fabric, this suit gives off classic menswear vibes - but tailored to modern day specs.

If you need a bit more insulation, throw on an extra layer like our turtleneck sweater.


Our biggest gripe with the shoulder season is how unpredictable precipitation can be. Sometimes it starts to rain out of nowhere. And later in the season, there’s sloppy wet snow. Or maybe, the clouds part for a glorious day in the sun. We wag our fists at you indecisive sky!

It’s a complete mess out there, but with the right jacket, it won’t ruin your mood. Keep a casual weather-resistant jacket handy - relaxed styling but with the potential to be dressed up. Like Daniel Hechter Paris’ Field Jacket. Able to withstand rain and wind, Daniel Hechter kitted it out with a removable liner for versatility. It’s all about the flexible layering y’all.

Surviving Fall with Tip Top

Every season has its specific needs and nuances. And being ready for the lies that the weather person spews the weather report means that you can go about the fall in comfort.

Swing by your local Tip Top location and see how we can help you! Or shop 24/7 online.

Tip Top Locations

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