Top 5 Fall Shoes You Need in Ontario + How to Choose the Right Pair

The leaves are turning, the air is crisp, and it’s time to trade in your sandals for something cozier, chicer, and more weather-ready! Fall in Ontario is beautiful, but the weather can be unpredictable. You need footwear that handles a morning frost, an afternoon walk, and a surprise rain shower without skipping a beat.

At Cheslers Shoes, we’ve hand-picked the best styles that blend fashion and function for your life in Ontario, whether you're heading to the office, running errands, or enjoying a weekend getaway.

Here are the Top 5 Fall Footwear styles you need this season, all stocked here at Cheslers!

 

1. The All-Day Comfort Clog: The Birkenstock (Birkenstock Buckley or Boston)

 

This year, the ultra-comfortable clog continues its reign as a fall staple. Perfect for a cozy yet polished look, clogs are ideal for transitional weather and the ultimate "comfy casual" shoe. Cheslers stocks a range of styles like the Birkenstock Buckley (a great slip-on shoe with a cozy feel) or the Birkenstock Boston (the classicBirkenstock clog).

  • Why it works for Ontario: It’s an ideal indoor/outdoor slip-on shoe for those early fall days. Just pair it with a cozy sock for extra warmth when the temperature drops.

  • Buying Tip: Look for styles with genuine cork or contoured footbeds for superior arch support, especially if you're on your feet all day.

 

2. The Classic Ankle Boot: The Rieker or Remonte Bootie

 

A quality ankle boot is the most versatile piece in your fall wardrobe. It pairs equally well with tailored trousers for work as it does with jeans and a chunky knit for a weekend lunch. Look for brands like Rieker and Remonte (both frequently stocked at Cheslers) which offer excellent style without compromising on comfort or durability.

  • Why it works for Ontario: Ankle height provides protection from puddles and cool wind. The right pair will have a sturdy heel and a non-slip sole, which is key for wet sidewalks.

  • Buying Tip: Choose a rich leather or nubuck for a classic look, or explore this season's trending colours like burgundy or dark brown.

 

3. The Polished Loafer: For Office & Errands

 

Whether you prefer a classic menswear-inspired Oxford or a modern, chunky Lug Sole Loafer, this style brings an immediate polish to any outfit. They bridge the gap perfectly between a dress shoe and a casual flat, making them a go-to for the 25–60 age group.

  • Why it works for Ontario: It’s the perfect shoe for professional settings or for days when a boot feels too heavy. Pair them with a cropped pant or tights for a sophisticated look.

  • Buying Tip: A thicker sole (like a lug sole) not only adds a trendy element but also provides better grip and insulation than a thin dress shoe.

 

4. The Reliable Waterproof Hiker: Merrell & Keen

 

For those who spend their fall weekends enjoying the beautiful trails and scenery (or just tackling a wet grocery run), a comfortable, reliable waterproof hiker is non-negotiable. Cheslers offers brands like Merrell and Keen Canada that specialize in comfortable, protective footwear.

  • Why it works for Ontario: Waterproof construction is a must to keep your feet dry during our wet fall season. These shoes provide superior traction for slippery, leaf-covered paths.

  • Buying Tip: Look for a lightweight yet durable design. Check for a waterproof (WP) rating and a deep, multi-directional tread on the sole.

 

5. The Slip-In Sneaker: Skechers

 

For pure, everyday comfort, nothing beats a well-made sneaker. This season's trend is all about the "Slip-Ins" from brands like Skechers—easy to put on, supportive, and stylish enough to wear beyond the gym.

  • Why it works for Ontario: Ideal for quick errands, school drop-offs, or casual weekend walks. They are the ultimate grab-and-go shoe for your busy lifestyle.

  • Buying Tip: Ensure the sneaker offers proper arch support (like the Skechers Arch Fit styles) and a durable sole to handle varied walking surfaces.

 

How to Choose the Right Pair for YOU

 

When investing in fall footwear, especially in a place like Ontario, prioritize these three things:

  1. Water-Readiness: Our fall can be wet. If a shoe isn't already waterproof, it should be made of a material (like leather or nubuck) that can be easily treated.

  2. Support and Comfort: You'll be spending more time in these shoes than a summer sandal. Look for cushioned footbeds, non-slip soles, and brands known for comfort, like Rieker, Remonte, Birkenstock, or Naot.

  3. Proper Fit (Especially with Socks!): Remember that you'll be wearing thicker socks. When you try on your shoes, wear the kind of socks you plan to wear most often in the fall to ensure a comfortable fit that doesn't pinch or rub.

 

Your Bonus Tip: Protect Your Investment!

No matter what style you choose, keeping it protected is key to longevity.

We carry a wide selection of shoe care in our stores.  

Different materials can require different care, so be sure to ask your staff member what is right for your new shoes or boots.  We have gentle cleaners, nourishing polishes, protector sprays and salt stain removers.  

 

Ready to Step into Fall?

Don't wait until the first downpour! Your perfect pair of fall shoes is waiting. Whether you’re ready to try on the latest Rieker ankle boots or slip into a new Birkenstock, we have the selection and expertise to find your sole-mate.

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