Pouch Perfect
The Blamo steps in where a formal briefcase is too much and a backpack is too casual—with more versatility than either. Sport Oliberté’s messenger bag over the shoulder or unhook the strap and carry it as a tote. A cavernous interior stores larger items while a smaller pocket on the outside keeps a smartphone in reach. The brand supports sub-Saharan African workers’ rights, making this one accessory that suits your needs while supporting someone else’s.
$220; oliberte.com

Head Gear
The nostalgia that comes with the variations of this stylish topper ranges from Humphrey Bogart to Big Bambu rolling papers. The Hiro Tribly, $150, provides a sharp look—its downturned front and upturned back brim make it casual Friday acceptable. Sport the natural woven straw Tribal Player, $50, with flip-flops on laid-back beach weekends. Or, for a classic, Sinatra style choose the Chanin Porkpie’s flattop, $98.
All by Kangol. kangol.com

Tread Lightly
Espadrilles have never been popular with men… until now. The natural design has been featured on more graceful soles for endless summers past, but this time the jute rope base takes a step into the man’s world. Ted Baker London combines light fabric with a classic sneaker design to create the perfect dock to dockside dining footwear of the season.
Drill 2, $110; tedbaker.com