Casual Dress Shoes

Stiff shoes step aside. Enter: Casual dress shoes for men that toe the line between business and pleasure. Laidback without sacrificing superior style, casual dress shoes offer the perfect middle ground for casual Fridays and cocktail hours alike. With an assortment ranging from dress sneakers to driving shoes, penny loafers to deceptively comfortable oxfords, you'll find no shortage of options here.

Dress Sneakers for Men. Dressing up a pair of kicks is a fine art, but our selection makes it super simple. Whether you prefer a sleek, no-frills sneaker from To Boot New York or a sneaker-soled oxford from Cole Haan, dress sneakers provide peak comfort while exuding a put-together vibe suitable for a slew of social events. And, they're an essential for every business-casual rotation.

Casual Loafers. Instantly upgrade any low-key look (without feeling overdressed!) with a pair of loafers. Slip them on as you head out the door or frame your entire outfit around them--either way, you'll look sharp in leather and suede textiles in a range of hues both neutral and unexpected. Consider best-selling casual loafers from Bruno Magli, Santoni, and more.

Driving Shoes. Characterized by flexible, grippy soles, driving shoes are the sportier sibling of the loafer. Designed to be more responsive to pedals, the sports car is decidedly optional when it comes to this silhouette. Luxury brands like Gucci, Ferragamo, and many more navigate the landscape effortlessly with drivers in soft, supple leather. Wear these preppy yet casual dress shoes to elevate any weekend fit.