
The problem with 99% of running shoes is that they are so blinged out with technology and space foam and glo-sticks and nano-fibers that they might as well be from the future. As timeless looks tend to be a little more stylish, shoes from 2016 don’t quite fit the bill. A good rule of thumb, I think, is that if you could actually use a shoe for some kind of athletic training or competition, it is probably best left to the track or gym. Instead, try one of the following upgrades:

1-2. Go canvas. Chucks ($95) are timeless and comfortable. Seavees Pantone Oxfords ($110) revitalize California casual from the ’60s — before west coast style turned really weird.
3-4. Go vintage. Classic New Balance 420s ($59) and vintage-esque Nikes Elites have all the modern running shoe comfort without the just-in-case-I-need-to-prove-how-fast-I-can-run vibe.
5-6. Go boating or driving. Deck shoes and driving mocs are good, casual slip-on options for stepping out on the weekend. The Band of Outsiders ($215) take on the Sperry Topsider rocks pretty hard, and Cole Haan ($148) makes solid standard loafers and drivers.