Best Comfortable Men’s Shoes for Fall


Fall is a time for cozy sweaters and comfortable shoes that can keep up with your active lifestyle.

Whether you’re sauntering through a leaf-strewn park, commuting to work, or just relishing the cool fall breeze, the right footwear can significantly boost your comfort and fashion.

The Importance of Comfortable Footwear

Before we delve into our top choices for autumn footwear, it’s crucial to understand just why shoes that offer comfort are so important.

Your feet serve as the base of your body, and if they lack proper support, it can lead to various issues such as foot pain, leg discomfort, and even backaches. Ill-fitting shoes can also impact your posture, and even your overall health.

The correct pair of comfy autumn shoes can enrich your experience, permitting you to soak in the season’s charm without worrying about discomfort or tiredness.

1. Chukka Boots

Chukka boots are a versatile and stylish option for fall. These ankle-high boots typically feature a two or three-eyelet lace-up design, making them easy to slip on and off.

Chukka boots are known for their comfort, thanks to their cushioned insoles and soft leather uppers. They provide excellent support for your feet while adding a touch of sophistication to your look.

Whether you’re pairing them with jeans, chinos, or even a suit, chukka boots are a fall essential.

2. Sneakers with a Twist

Sneakers aren’t just for the gym anymore: fall is the perfect time to embrace the sneaker trend with a twist. Look for sneakers with weather-resistant materials like leather or suede, which can handle the occasional rain shower.

Brands like Nike, Adidas, and New Balance offer stylish and comfortable sneaker options that provide excellent arch support and cushioning. These sneakers are perfect for casual outings and can be paired with a wide range of outfits, from jeans to joggers.

3. Loafers

For those looking to maintain a touch of elegance while staying comfortable, loafers are an excellent choice.

Loafers come in various styles, including penny loafers and tassel loafers, and are available in both leather and suede. They slip on easily, and are perfect for both casual and dressier occasions. Look for loafers with padded insoles and arch support for added comfort during long walks.

4. Hiking Boots

If you anticipate spending considerable time outdoors during the autumn season, it would be wise to invest in a high-quality pair of hiking boots. Designed for optimal comfort and support, these boots are perfect for activities such as hiking, camping, and exploration.

Seek out boots with waterproof capabilities to ensure your feet stay dry in damp conditions. Brands like Merrell, Columbia, and Timberland offer a broad selection of hiking boots tailored to various terrains and weather scenarios.

5. Chelsea Boots

Chelsea boots are an enduring classic that never falls out of fashion. These pull-on boots are characterized by an elastic side panel, facilitating easy wear and removal.

Known for their comfort and versatility, Chelsea boots are an exceptional choice for the fall season. They pair seamlessly with both casual and semi-formal attire, and options with cushioned insoles and supportive outsoles are available to keep your feet comfortable throughout the day.

6. Moccasins

Moccasins epitomize comfort and coziness. These slip-on shoes are generally crafted from supple leather or suede, and feature a flexible sole that conforms to your foot’s shape.

Ideal for lounging at home or running errands on a relaxed autumn weekend, moccasins come in a variety of styles, encompassing traditional Native American designs and contemporary interpretations.

7. Waterproof Boots

As fall weather can be unpredictable, having a pair of waterproof boots in your closet is a smart move.

Waterproof boots are designed to keep your feet dry and comfortable even in heavy rain or snow. Look for options with insulated linings to keep your feet warm as temperatures drop.

Brands like Sorel, The North Face, and Keen offer a range of waterproof boots that combine style and functionality.

8. Slip-On Shoes

For those looking for the ultimate convenience, slip-on shoes are a great choice.

Whether they’re in the form of slip-on sneakers, boat shoes, or casual loafers, these shoes are easy to put on and provide all-day comfort. Look for options with memory foam insoles or cushioned footbeds for added support.

Slip-on shoes are perfect for casual outings or days when you’re in a hurry.

9. Wingtip Brogues

Wingtip brogues are a stylish and sophisticated option for fall. These dress shoes feature decorative perforations on the toe cap and along the seams, giving them a unique and distinguished look.

While they may appear formal, many wingtip brogues are designed with comfort in mind, featuring padded insoles and supportive outsoles. They’re perfect for dressing up your fall outfits for special occasions or work events.

10. Suede Desert Boots

Suede desert boots are a fantastic addition to your fall footwear collection. These ankle-high boots are lightweight, comfortable, and stylish, and their soft suede material provides a cozy feel for your feet, making them perfect for casual outings. Pair them with jeans and a sweater for a classic fall look.

Brands like Clarks and Desert Boot Company offer high-quality suede desert boots in various colours and styles.

Are Suede Shoes Suitable for Fall Weather?

Suede shoes can be a great choice for fall, but it’s essential to make sure you are taking care of them properly.

Suede is a soft and luxurious material that adds a touch of sophistication to your fall outfits. However, suede is more susceptible to water damage than other materials like leather.

To keep your suede shoes looking their best, use a suede protector spray to make them water-resistant. Additionally, avoid wearing suede shoes on particularly rainy or slushy days, and be sure to brush off any dirt or debris regularly.

With proper care, suede shoes can be a stylish and comfortable addition to your fall footwear collection.

How Do I Choose the Right Size for My Fall Shoes?

Choosing the right shoe size is crucial for comfort – different brands and styles may have slightly different sizing, so it’s essential to measure your feet accurately and refer to the brand’s sizing chart when purchasing shoes online.

Remember that your feet can change size over time, so it’s a good idea to measure both feet and choose the size that accommodates the larger one. It’s also important to consider the type of socks you’ll be wearing with your fall shoes; thicker socks may require a slightly larger size for a comfortable fit.

When trying on shoes in-store, walk around and ensure that there is enough room for your toes without feeling too loose in the heel or sides. Comfortable shoes should have some wiggle room for your toes and should not cause any pressure points or discomfort.

Can I Wear Orthotic Insoles with Fall Shoes?

You can often wear orthotic insoles with fall shoes to enhance comfort and provide additional support. In fact, many comfortable men’s shoes come with removable insoles, which allows you to replace them with custom orthotic insoles if needed.

Orthotic insoles are designed to address specific foot conditions and provide extra cushioning and arch support. If you have foot issues or require orthotic support, make sure to choose shoes that can accommodate orthotic insoles comfortably.

When choosing your autumn footwear, consider options with spacious designs or insoles that can be replaced, allowing for the inclusion of your personalized inserts. This approach ensures you can maintain your foot health while still enjoying style and comfort during the fall season.

At the end of the day, as the leaves start changing colours and temperatures start to drop, having the correct pair of comfortable shoes is crucial for making the most of the season. Depending on your preference, you might opt for the timeless appeal of chukka boots, the adaptability of sneakers, or the sophistication of loafers – there are numerous choices available, so invest in superior-quality footwear that gives your feet the support and comfort they need.

To discover the most comfortable men’s shoes for autumn, think about your fashion inclinations and the activities you’ll be participating in. Whether it’s casual weekend outings or adventurous outdoor excursions, there’s an ideal pair of shoes out there for you.

For a diverse selection of comfortable men’s shoes for the autumn season, consider visiting us at Walking on a Cloud. Our wide array of footwear choices ensures you’ll find the perfect pair to keep you both comfortable and stylish throughout the season.