A New Vintage Shop Is Coming to Milwaukie

Best of Luck, Outpost is part of a wave of new businesses transforming downtown Milwaukie into the next great destination for vintage shoppers.

Juan Carlos Montoya News Writer
Best of Luck Outpost Logo (Image credit: Best of Luck Outpost Instagram)

Best of Luck Outpost, a new secondhand and vintage shop from co-owner Tiffany Diaz, is set to open at 10909 SE Main Street in downtown Milwaukie, inside the historic Perry’s Pharmacy Building, which is currently being transformed into a cluster of independent small businesses. Diaz confirmed to What Now Portland that no opening date has been set yet, as the project is still waiting on a few outstanding items from the city before moving forward.

The shop will be one of two secondhand stores opening side by side on the block, with Salon Fernweh tucked in between them. While details on the concept remain limited, the name alone says a lot: Best of Luck Outpost carries a spirit of adventure and wandering that feels right at home in a building with a century of stories baked into its walls.

The Perry’s Pharmacy Building, once home to the Main Street Collectors Mall and Soda Fountain, is being carefully restored into a collection of independent storefronts. The project received grant funding from the City of Milwaukie to help make the spaces accessible to first-time small business owners, and the lineup taking shape is one of the more exciting things to happen to downtown Milwaukie in years.

 

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Juan Carlos Montoya discovered his love for storytelling through sports, creating social media content in high school before pursuing a bachelor's degree in Journalism in Costa Rica, where he graduated in 2025. Since then, his career has taken him through the halls of Teletica Radio, the biggest mass communication company in Costa Rica, and into the world of digital media as a Social Media Manager for an iGaming platform. Originally from Honduras, Juan Carlos brings a global perspective to every story he tells. He believes that every interview is an opportunity to make a genuine human connection, and that food is one of the most powerful ways to understand a culture and its roots. When he's not tracking down the next big opening in Sacramento or Portland, he's probably watching Football, or planning his next adventure. What Now is his new home, and he's just getting started.
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