The Do-It-All Sneaker
New Balance 247 Classic / 247 Sport
Regardless of some of their recent statements about our political leadership, New Balance still makes a damn good shoe. The "Classic" comes five solid color blocks that lend themselves to the office and weekend day trips. The "Sport" is the more casual of the pair, but just as much of a workhorse. The lightweight look may not work for everyone, but it dresses up and down. Plus, the glove-like fit is great for airport security lines (no need to untie laces).
Unless you're a high-powered businessperson or litigating in court several days a week, there isn't much need to have multiple pairs of dress shoes. I'm always on the lookout for a pair that can do double duty: formal enough for an important meeting, but can dress down for a night out too. I've had the opportunity to wear a tan suede pair around town and they're the perfect mix. The wingtip design is more professional, but the rubber sole keeps you light on your feet all day. A summer staple for sure.
The Unlikely Hi-Top
Ben Sherman Men's Conall Hi Fashion Sneaker
When I picked these up three years ago at a big-name discount store in San Francisco, I didn't think I'd still be rotating them today. They're unbelievably comfortable and stand up to a ton of abuse given they're denim on the exterior and some kind of durable poly inside. As an added bonus, the soles are fairly waterproof. For rainy jaunts on our cracked and pothole-laden streets, they're a winner.
I think my first pair of slip-ons was classic Vans (not checkered, but solid color, thank you very much). As I got older, I loved the convenience, but needed to graduate to something a little more refined. I bought a pair of Dune's awhile back and they got more comfortable with age. They have clever styling and a cool southern Spain-meets-California vibe. A pair in your favorite color combo plus no-show socks is a winner.