In 1997, NW 23rd Avenue was my perfect shopping excursion. At age 17, my best girlfriends from my uptight religious high school (where I would regularly get sent to the principal’s office for dress code violations) and I would cram into my tiny Mercury Capri with leaky windows, make the crucial decision between Soundgarden’s Down on the Upside or Fiona Apple’s Tidal, and head north from Salem.

After parking illegally in the Zupan’s Market lot (sorry, Zupan’s!) we’d run across Burnside and gleefully pop into incense-wafting shops along NW 23rd, feeling impossibly cool. Requisite stops included Ipnosi for a dragon-print dress or black faux-fur lunchbox-style purse and Music Millennium to flip through new CD releases (or catch an in-store show if we were lucky). Then we’d end up sipping jasmine tea on the steps of Anna Bannanas café.

A couple of years later I would permanently escape my suburban Salem life, moving to Stumptown to attend college—and switching my shopping allegiance to Southeast Portland in the process. At Gold Door, just off equally incense-laden Hawthorne, I ogled the first tarot deck I had ever seen, as well as massive gem jewelry. I spent hours bargain-hunting at Red Light Clothing Exchange. A few blocks away on Belmont I was introduced to the idea of local design at the birthplace of our indie fashion movement, Seaplane.

The love of exploring these shops—joyfully taking in each new window display, the smell of vintage clothes when you open a jingling belled door—helped push me into the role of Portland Monthly’s style editor, a post I’ve held for the past decade. In that time I’ve seen the closure of too many shops I’ve admired—Isaac Hers, Eden (no relation), and Radish Underground—to name a few. But the thing about scrappy entrepreneurial Portland is that awesome new spots also continue to open and flourish.

Along with a baffling holiday mascot, a helpful local gift guide, and Die Hard: The Musical Parody, our last pages of 2019 are devoted to small shops doing fantastic things right now. There’s N’Kossi’s Jean Pierre Nugloze, who uses textiles from his hometown of Lomé, Togo, to make stunning tailored suits; Workshop Vintage, which has raised visual merchandising to an art form; Shipwreck!, a spot that joyfully denounces minimalism for color explosions, and more.

In other words, the kind of shops you can walk into and feel impossibly cool.