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We know Pioneer Square as one of the oldest, most historic Seattle neighborhoods, but whoever said that meant boring and outdated? Okay, so maybe no one has actually said that. Either way, we're debunking the rumor. Situated in this section of the city, popup coffee shops and vintage boutiques abound. There's a lot this neighborhood does well, but shopping may just be at the top of the list. 

Bon Voyage Vintage

If the first thing you think of when you hear the word vintage is neon, then Bon Voyage is your kind of store. Rows of dresses, shirts, and fringe jackets line this outlet with finds that call back to the glamor of eras past. With an Instagram full of stylish ideas and a boutique full of threads to make them happen, Bon Voyage will set you up on your retro fashion journey.  

Callus

This part-time popup hub, full-time coffee shop is a little hard to pin down. It hosts rotating events—doughnut previews, art shows, plant workshops—so there’s always something new and different to check out. Light, open space pairs perfectly, it turns out, with fresh brewed coffee and the surprise of that week’s feature, be it a mother-daughter painting duo or a month-long yoga popup.  

Clementines

There comes a time in a lot of women’s lives when comfort and style need to meet halfway. It is usually right around then that these women end up at the little shoebox of a shop called Clementines. Heels, boots, booties, loafers, and sandals by Chie Mihara, Corso Como, Repetto, Giraudon, and others make use of sound engineering, quality materials, ultra modern color combinations, and an ever-so-chunky elegance. Count on owner Linda Walsh not only for her always-surprising and tempting inventory but also for striking, shapely eyewear and great conversation. —Rosin Saez

Curated Vintage

Nestled in this historic Seattle district, Curated Vintage brings fun handpicked items to women’s fashion. The minimalist interior of pristine white walls set against a dark wood floor only adds to the aesthetic of this artistic fashion stop. With both modern and classic styles, it’s basically the closet you’ve always dreamed of.

Division Road, Inc.

Much of the “luxury heritage” clothing at Division Road looks akin to the old-school cool of American journeyman garb seen in black-and-white photographs. Think crisp denim, Japanese flannel, and leather cap-toe boots—sold alongside modern pullovers, flannels, crewnecks, and cardigans. With designs from manufacturers in Western Europe, North America, and Japan, Division Road takes over 30 different brands and sets you on the sartorial path less traveled.

Ebbets Field Flannels

Ever want to look like an old-timey pitcher for the Seattle Rainiers? Or maybe the Portland Beavers? Ebbets Field specializes in authentic flannels and ball caps from the long-departed baseball teams enshrined in your grandparents’ memory. Jerseys and jackets, too, it’s all here. Plus, tailored references to pioneering athletes (see: the EFFA Collection, named after Effa Manley, the first and only woman ever to be inducted into the Baseball Hall of Fame). This shop goes far beyond any sports field.

Flora and Henri

Owner and designer Jane Hedreen launched her children’s clothing line in the late ’90s, and, after shuttering her downtown brick-and-mortar to go full internet in 2013, she’s officially back. A light-filled showroom houses her designs alongside home goods and fashions for the whole family, the one whose house always seems to have the sleekest gadgets and tome-stocked book shelves. —RS

Fruitsuper

The folks behind Join Design have rebranded—it's Fruitsuper now, named after the owner and couple's art moniker—and they're opening a new shop in Pioneer Square. The same artist-owners’ collective ethos will live on at this location (524 First Avenue South), which opens in the first week of September. What will differ: a lovely adjoined wine tasting room. Wine plus fine design and artistically crafted goods? Yes, please. —RS

H. Bailey Curated Retail

Hilary Bailey Burnett, owner and curator of this little boutique, crafts a unique style for each person that she sees in her store. The “menswear for all” shop specializes in clothing that somehow combines styles both classic and ornate into a fit that always hits the mark. The best part: Inclusion is a driving force here (#genderdiversefashion is a frequent Insta tag). Just make sure you love your purchase because, unlike fashions of yore, clothing returns can’t come back.

Swan Dive

Located inside Clementines, this vintage boutique shop spotlights fashion from the 1950s to the early aughts. Designer brands are also in store like Chanel, Saint Laurent, and Kenzo—but the real draw of this simple spot is its little finds. Like a hand-painted perfume bottle and matching jewelry holder for your dresser, or the perfect denim vest that fits oh so right. 

Velouria

Quite the contrast to the surrounding stadiums and sports bars, this expansive trove offers everything from billowy jumpsuits to minimalist jewelry to natural skin care, much of which is sourced within the Pacific Northwest. Plus, the store donates a portion of each sale to a different nonprofit every month so shopping has a little bit of a philanthropic bent to it. —RS

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