Never underestimate the power of a sister act. For two decades, Jennifer and Monica Ransdell fed crowds at Portland’s original velvet-painting cave, sock-monkey heaven, and hipster paradise on SE Clinton Street: Dot’s Café. The bespectacled 40-something sibs sold the restaurant last year, then jumped back into the game with a charming retro diner, slinging thrifty sandwiches, peppery soups, and dynamite baked goods. Lily Day just opened in February but already feels like a neighborhood institution. 

Masters of mood, the Ransdells now draw on ’50s-era woodcuts, Doris Day record covers, piped-in jazz, kitschy salt and pepper shakers, and oddball coffee cups. Regulars tuck into snug red booths, sip old-school Kobos coffee, and dive into monstrous toasted sandwiches packing goat cheese, garlic, bacon, shredded zucchini, and vegan-friendly soyrizo.

The starting point for most breakfast sandwiches is a creamy baked egg nested between soft slabs of grilled, buttered sourdough. Our favorite stacks on pepper jack cheese, corn nubbins, and an addictive house-made green chile sauce. Come lunchtime, crunchy carrots and puckery pepperoncini sneak into grilled cheese sandwiches and enliven vegetable soups fully stocked with orzo, kale, and cauliflower. Down-home sweets like funky butterscotch cornflake cookies come courtesy of Monica’s daughter, Violet VanDell. The 19-year-old’s loaves of super-moist, pineapple-packed carrot coconut cake are worth their own pit stop.

Despite its demure, kid-friendly demeanor, Lily Day’s bar is well stocked. The Ransdells will happily pour you a “Red Eye Flight” any time of day: a glass of vodka on the rocks served with side shots of Bloody Mary mix and grapefruit and orange juices. So this is what it tastes like when hipsters grow up.