When you’re planning a long walk through the city, the right footwear can make all the difference between an enjoyable adventure and a painful ordeal. Walking through metropolitan areas demands constant adaptation to rough sidewalks, sloped curbs, packed sidewalks, and unpredictable ground conditions. That’s why choosing the right shoes isn’t just about comfort—it’s about preventing injury and staying on your feet longer.

Start by looking for shoes with good arch support. The pressure on your feet during daily urban hikes is far greater than most assume. Shoes with built-in arch support help distribute your weight evenly and reduce fatigue in your feet, ankles, and legs. If you have specific foot needs, like flat feet or high arches, consider adding orthotic insoles to your chosen pair.

Cushioning is another key factor. Choose midsoles that dampen impact while retaining stability. A midsole made from materials like EVA foam or rubber blends offers a balance between support and comfort. Overly cushioned soles compromise your balance on uneven urban surfaces. You want enough padding to protect your joints but enough firmness to keep you moving efficiently.

Breathability matters too. Your feet will sweat during a long walk. Damp shoes can lead to blisters or fungal issues. Choose shoes made with breathable mesh uppers that let air circulate while still offering enough structure to protect your feet from debris and the elements.

The fit is non-negotiable. Leave enough space—roughly the width of your thumb—for your toes to extend naturally. Your heel should stay snug without slipping, and your toes should have room to wiggle. Size can vary by brand, day, and even time of day. Try on shoes in the afternoon when your feet are slightly swollen.

Avoid overly stylish or rigid shoes like dress shoes, bonnet stone island high heels, or stiff leather boots unless they’ve been properly broken in. While they might look good, they often lack the flexibility and support needed for hours of walking. Instead, opt for athletic or walking shoes designed specifically for urban environments.

Many walkers swear by brands that specialize in walking technology. But you don’t need to spend a fortune. Visit stores that allow you to walk around and return if they don’t feel right. Take a brisk lap around the showroom to test stability and pressure points.

Lastly, replace your shoes regularly. Visual condition doesn’t reflect internal wear—foam compresses silently. Most walking shoes last between 300 to 500 miles. At five miles per week, expect replacement within half a year.

The best footwear for long city walks is the one that fits your feet, supports your body, and feels comfortable from the first step. Prioritize function over fashion, and your feet will thank you when you’re still walking strong at the end of the day.