Wandering without a map and an open mind yields the best results. We had been looking for a gallery-like retail space called Kapok when we stumbled upon a more unique and sophisticated pocket of style in a relatively quiet, elevated area of Wan Chai. Grouped with Moon Street and Star Street, this area was dubbed the Starstreet Precinct (more here). Kapok's fun book spread and eclectic chocolate package design was refreshing, with the backpack selection standing out the most.
We continued down Sun Street toward the seemingly dead end. We entered a men's shop with perfectly tailored shirts and funky shoes, discovering an exit on the other side of the store that negated the dead end of Sun Street and led us to St. Francis Yard. There we found another Kapok (tie and bracelet purchases made) and Monocle, an IRL version of the publication.
The unnamed men's store up top was called F.I.L. (updated main photo, replaced map below) and Yo Ma Ma was just ok. Cool that you could pay with an octopus card...even though we didn't. Still haven't made it to Ovo.
Update number two:
W.D.S.G. Art & Craft was another store worth popping into in the Starstreet Precinct. It's vintage-inspired (and some actually vintage) goods that exhibit wonderful craftsmanship with unnecessarily high price tags. We liked the style and the underground feel.