The next best thing to ridiculously good looking?

Clothes that transition between casual and dressy occasions with ease. They’re the chinos you wear for work and for play; The man cardigan you wear on the weekdays and the weekends; The plaid shirt you wear for running errands and for grabbing drinks.

If you’re looking to expand your dual-purpose wardrobe, consider Sperry Top-Sider’s fall collection, featuring new designs and collaborations that pair equally well with dark wash jeans or a gray tweed suit:

Traditionally a summer shoe, it’s been released in materials like flannel and suede for fall:

J. Crew Sperry Top-Sider Authentic Original Nubuck Chukka ($125)

Band Of Outsiders Chukka Boot ($318)

Now the only question is, socks or no socks?

Photos: J. Crew, Steven Alan