The shop, opened in January, reincarnates the original Winn Perry, which operated in Southeast Portland between 2008 and 2011. Back then, the operation’s taste for Americana-rooted (and often US-made) rarities like Alden shoes (some topping $500 a pair), Falke socks, and Individualized shirts stood out as the most eclectic style source for Portland’s khaki-clad menfolk. Different shop, different neighborhood, different era: the new Winn Perry does business in a micro-district bristling with workboots, selvedge denim, and natty-but-brawny shirts. Nearby, Danner Boots, Tanner Goods, Poler, Self Edge and others all serve a classically inclined, quality-obsessed clientele shaped by the recession-era “heritage” trend. Even so, Sayler offers a particularly refined vision of male style, with a tight apparel selection and select lifestyle accessories that walk that crucial but fine line between awesome and ridiculous. (Nested stainless steel drinking glasses with leathern caddy, from England’s Daines & Hathaway: $130.) Various curios—a wall-mounted collection of walking sticks, a Stanley Thermos, deep stacks of vinyl—set a certain tone: call it Gentleman Badass.

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