3. Vans Old Skool

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Vans are perhaps the most popular casual shoe of all time. These versatile and affordable sneakers are available in nearly every color imaginable, allowing you to have multiple pairs for various outfits. While some colors are a bit too much for the average man who prefers a more neutral palette, their Old Skool shoes in both black and white are perfect for everyday living. 

Unlike some other casual shoes, these Vans are not as easily dressed up, however, they’re very comfortable once broken in, making them a consistent and dependable option for long walks or busy days where sitting down is not much of an option. 

4. Converse Chuck 70 High-Top Canvas Trainer

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The day that Converse goes out of style truly is the day that pigs fly. Perhaps the ultimate casual shoe, Converse boasts style and comfort, leading to their 50-year long grasp on the casual shoe market. 

These Converse Chuck 70 High-Top Canvas Trainers are a clean, white sneaker that have a bit of an edge due to the height of the high-top. While Converse are typically seen as being very casual and difficult to dress up, they tend to make their own fashion statement being that they are one of, if not the, most iconic masculine shoe of all time. 

5. New Balance 247S

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If you’re the kind of guy who prioritizes comfort over style, then the New Balance 247S might be the perfect sneaker for what you are seeking. These very basic tennis shoes come in black and navy blue.

These lightweight and flexible sneakers are perfect for the man on the go, complete with a breathable mesh material and laces that allow for a perfect fit to any foot shape. Though the style might not be up-to-date enough for some guys, they’re virtually unbeatable when it comes to being able to wear them all day long without pain or discomfort.