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

We didn’t find any lumberjack-chic shirts this weekend but we did spot these ridiculously cool retro sneakers by Generic Surplus:

Generic Surplus Wing Tip in Gray Or White Suede $72 (White Suede on sale at Urban Outfitters $39.99)

Half wingtip, half sneaker – they’re a great intermediary shoe that will fit right in between your Converses and Ferragamos. While the wingtip accents are reminiscent of 60s sophistication and days past, the sneaker form keeps the style fresh and modern.

Pair with jeans or chinos, they’re perfect for your not-a-boy, not-yet-a-stuffy-old-grown-up style.

Tired of black socks day in, day out? Mix it up by going commando (socks, that is) a la Shia LaBeouf and David Beckham.

Dress down a suit like Shia or dress up a casual outfit like shorts and a t-shirt with a pair of loafers-sans-socks. It’s versatile, modern, and of course ridiculously good-looking.