The Pearl is Portland’s resident glamazon, primped and coiffed to match its well-heeled residents. After flying high for years, the area has been hurt by the downturn in the high-end condo market and chain stores are holding down much of the real estate on the district’s western fringes. 

Still, there are plenty of gems to be found, fueled by morning coffee and the killer breakfast menu at Sisters Coffee Company or Moroccan mint tea and scones made fresh daily at Ovation Coffee & Tea by the family matriarch, known to regulars as “Momma Dee.” The shop is at the base of The Fields Park, one of the city’s nicest open greenspaces that begs for flying a kite on a windy day and boasts views of the Fremont Bridge. The Pearl also boasts a branch of Barista, beloved by hard-core coffee fans citywide, with a perfect deck area for people-watching.

If a cozy nook and page-turning read is more your jam, hop a streetcar to Powell’s City of Books, a book lover’s mecca that spans more than 68,000 square feet. A few blocks up Burnside, Everyday Music, is a vinyl and CD haven, where artsy Gen Z’ers can experience the magic of crackling Zeppelin records and anyone can try to sell their currently-gathering-dust-in-the-basement collections. There are endless opportunities to overdraw your back account: try House of Lolo for women’s clothing in buttery silk fabrics, MadeHere PDX for local artisan and designer pieces, or Cult for novelty items from Japanese vinyl to art books to Clockwork Orange figurines. 

 When the lights go down, find yourself at Botanist’s warm-weather-only rooftop deck for an evening of signature cocktails and soothing plant décor, or party at Pink Rabbit, where the drinks are inspired by ’90s rockers—order the kimchi fried rice to soak up the potables. 

If you’re hunting for a more upscale dinner option, try the cozy, candlelit Arden Wine Bar & Kitchen. A stool at the bar lands a front-row view of the open kitchen, where the chefs crank out handmade pastas.