For this sharp shoe designer, flying is all about unplugging and head-to-toe comfort.

As the creative director of Via Spiga—not to mention the talent behind a namesake line of women’s shoes and the men’s footwear brand Casbia—Edmundo Castillo has a pretty hectic life. Which is why he loves air travel: “It’s my time to disconnect and not have the phone ringing,” he says.

Castillo gets ample time to himself en route to factory visits in Milan (where he keeps an apartment), business trips in China, and vacations in Hawaii, the Dominican Republic, and his native Puerto Rico. In flight, he watches 30 Rock and Mad Men on his iPad, which he carries in a vintage-corduroy sleeve by Milan-based Pijama (from $38). When he wants to sleep, Castillo relies on his Beats by Dr. Dre headphones (from $200) because “they block all the noise.” As for his on-the-go outfit: “I usually land and go straight to work,” he says, “so it’s important to stay in style, but also feel comfortable.”

• The IWC GST Chrono Rattrapante watch was a gift from Castillo’s mother when he launched his first line.

• When traveling, Castillo opts for a practical and easy look: dark-colored, fitted shirts from J. Crew (from $27) and chino-inspired Incotex trousers (from $350) .

Casbia slip-on woven sneakers ($400) look both polished and sporty. “I designed them for travel,” he says.

• Inside this Sergio Rossi alligator tote—which Castillo designed when he was creative director of the brand— he packs leather Comme des Garçons zippered envelopes (from $134) filled with toiletries.