Whether kitted out for morning, noon, or night, Kelly Wearstler’s ensembles are much like her design projects: thought-provoking, dynamic, and endlessly creative.

Here’s what a new generation of dedicated craftspeople—from Tony Shirtmakers’ Tony Parrotti to Tildenshop’s Tilden Yamamoto—have learned from operating brands entirely on their own.

When “Creators in Fashion” took over VidSummit’s main stage in early October, the closing-night crowd witnessed something the ...