In 2025, we’re living in a world where men’s shoes can finally be both comfortable and HR-approved—a revolution in footwear! Few brands have mastered this balance as well as Cole Haan, which holds a special place in my heart, closet and eBay cart. They were among the first to do it right, blending comfort with office-ready style.

That said, a word of caution: buying used shoes can come with risks. A poorly fitted or worn-down pair can throw off your step, especially for runners. I learned this the hard way—after years of neglecting my footwear choices, I ended up needing foot surgery with Dr. Lindow three years ago. Now, I always prioritize comfort over style—but thankfully, we no longer have to choose between the two.