A cattle drive from a motorcycle seat, eight years with a Tokyo tattoo master, skydives in Panama. Josh Sirlin on men's lifestyle and the life skills you only learn by going.

Craft, menswear, Style, travelJosh SirlinSeptember 30, 2026life skills for men, mens lifestyle, adventure, cattle drive, motorcycle trip, horitoshi, harris tweed chore coat, josh sirlin, black bear brandComment

Twice a Year in Okayama

Denim is decided in the room, with the cloth in your hands. Josh Sirlin on his twice yearly denim meetings in Okayama: the rope dye house, the shuttle looms, and the sewing room.

adventure, Culture, Denim, Japan, Japan & Culture, travelJosh SirlinSeptember 28, 2026okayama denim, josh sirlin, japanese selvedge denim, rope dyeing, shinpaku, shuttle loom, botanical indigo jeans, denim mill, black bear brandComment

Black Bear Brand Tokyo: Ichirota, Josh, and a Painting Made for the Road

The artist Ichirota painted Josh Sirlin with the motorcycles that carried him across the American West. He is bringing the original to Tokyo and giving it to Josh at the Black Bear Brand pop up, where it hangs for all three days. 日本語は英文の下にあります。

The Road Humbles You: Travel, Curiosity, and Where the Work Comes From

Being the least capable person in the room is the fastest education there is. Josh Sirlin on travel, curiosity, and getting humbled on purpose.

Culture, Heritage, Japan, Japan & Culture, travelJosh SirlinAugust 5, 2026travel and creativity, living abroad creativity, japan travel, oita motorcycle, curiosity, humility, josh sirlinComment

The Milestone: What the Tollman Family Taught Me About Luxury

A hotel group named for a flower in a man's lapel, and a friendship that started with a customer buying a jacket. Josh Sirlin on the Tollmans and real luxury.

Culture, Style, travelJosh SirlinJuly 30, 2026red carnation hotels, the milestone hotel london, tollman family, brett tollman, luxury hospitality, luxury travel, josh sirlinComment

Travel, Culture, and the Making of a Creative Life

Every good idea I have ever had came from somewhere else. Josh Sirlin on how travel and other people’s cultures shape creative work, from Okayama to the Outer Hebrides.

travel, Craft & Materials, Culture, Style, Style & HeritageJosh SirlinJuly 20, 2026travel and creativity, cultural influence design, creative inspiration travel, design philosophy, josh sirlin, black bear brand story, travelComment

Travel, Exploration, and Style: The Wardrobe That Earns Its Place

The best travel clothes work as hard as you do and look better the more you wear them. Josh Sirlin on the wardrobe that earns its place on the road.

travel, Style, Heritage, CultureJosh SirlinJuly 15, 2026travel style men, travel wardrobe, one bag travel, selvedge denim travel, rugged style, black bear brandComment