Between the, um, entrepreneurial Depop girlies trying to pass off a 2009 graphic tee from Limited Too as “Y2K aesthetic,” and the dressed-to-the-nines-in-Supreme hype beasts who swear that the “rare” jersey they found at Goodwill for eight bucks is actually worth hundreds, it’s tough to know what’s truly considered vintage nowadays. Step foot into a dusty, maybe a little bit smelly (yet undeniably beloved) antique mall, stuffed to the brim with ceramic cats and someone’s abandoned Beanie Baby collection, and you can be pretty sure that you’ll leave with something as vintage as the person working the register. After quite a bit of digging, of course. 

But these six new- or newish-to-Portland vintage shops do the Goodwill-hunting for you, each one delivering the stars of every antique mall, estate sale, and thrift store in one, expertly curated storefront. And regardless of whether your definition of vintage is a cocktail dress from the ’60s or a Hannah Montana lunch box, these store owners all agree on one thing: the ultimate goal of shopping vintage is to “keep stuff out of the landfill.”

Wink Vintage
Best for: An organized mix of classics, statement pieces, and handmade clothing
The (previous) home of the cutest pair of handmade, sage green (swoon), wide-leg, linen vintage trousers I have ever put on my body, Wink Vintage in Southeast will forever hold a place in my heart. This shop looks like it up and walked out of a film student’s very-nostalgic-for-the-’70s Pinterest mood board. Amid the (ridiculously well-organized for a vintage shop) collections of denim, silk nightgowns, funkily patterned skirts and statement pants, and aloha-print button-ups and blouses you’d probably find in Jackie Burkhart’s closet exist the trendiest of locally made crochet bucket hats and made-from-vintage-fabrics patchwork halter tops and dresses. Not to mention a burnt orange sweater with a lace trim, an incredible chenille sweater featuring a visor-wearing Snoopy, and a classic, sparkly black dress from the ’90s. Irresistible. 7909 SE Stark St 

Kissing Booth
Best Collection of: Vintage Sweatshirts
What happens when five intimidatingly chill Portland dudes decide to open a vintage store? It’s like if high-end minimalistic retail, archival World War II jackets, the “classic vintage guy” aesthetic, and midcentury Architectural Digest décor all met in, ahem, a kissing booth. As you browse the expansive collection of ringer tees, sweatshirts from the ’40s, and the occasional Grateful Dead tee—you might find Michael, Cole, Gabriel, Payton, or Jacob sitting at the register while a song you want to (but won’t) Shazam plays overhead. The five merged their OG shops (Hellmart and Suite Zero) last June before opening Kissing Booth in September, and they try to find the oldest clothing possible. They’d follow a lead across the state to an abandoned building (again) if it meant sourcing another military jacket from 1910. 1111 SW Alder St & 805 N Killingsworth St

Program Shop
Self-Proclaimed Style: Grandma chic
From her expertly-crafted-under-the-influence-of-marijuana Spotify playlists she hopes will inspire customers to dance as they browse to the glowing ambience of artfully placed neon signs to the rattan shelves housing various for-sale plants and knickknacks to the furnished lounge area—Bree Myers cares a lot more about the art of curating Program Shop than she does pretending to know anything about fashion. The Albuquerque-born transplant opened the Program Shop in August 2021. Like life, she says, her space is constantly evolving—as she likes to showcase “new kids [vendors] on the block.” Highlights from my visit include the incredibly cool $1 postcards, the trendiest pair of slides (if you’re a size 8.5, book it over there before I do), dainty blouses, a darling drawstring crochet top from the ’70s, sunflower and watermelon hair clips, a cheetah-print button-up, floral potholders, and more. Some of which we left for you to find. 2122 SE Division St

Looking Sideways
Best: Prices. And clown masks, of course.
You might easily miss this hole-in-the-wall gem in Northeast Portland, but you’d regret it. Coralie “Crick” Hammerlee-Lewis opened Looking Sideways back in 2019. Though it definitely advertises its more eccentric collection of items—studded leather chokers, ceramic naked babies, and an incredible feet-having pot, to name a few—this place has tons of gender-neutral basics (which, if you’re an avid thrifter, you know, can be very hard to come by). There’s a gorgeous collection of floor-length skirts, vintage Liberty overalls for under $30 (quite frankly unheard of), and some killer athletic shorts and retro one-piece swimsuits. And every statement piece—the leopard print denim vest, the horse cardigan—you could see someone buying (both because of the affordability and the unique-but-not-too-much-of-a-statement aesthetic). 914 NE 28th Ave

Hello Sunshine
Style Tip: “We are all just cosplaying the apocalypse right now.... Be the main character.” 
Hello Sunshine looks as though Portland’s most stylish grandmas gathered their collection of ’60s mod dresses, one-of-a-kind tea towels, and groovy floral wall decals and set up shop on Burnside Street. Georgia-born sisters Binky Arnold-Compere and Tita Compere curate their store as though they are shopping for themselves. That means disco ball earrings, ceramic strawberry jars, and Yellow Submarine-esque photo ops, painted by Tita, at every turn. Not to mention the iconic pink floors—a.k.a. the shop’s “fragile masculinity repellent.” Although the 30-something sisters think of vintage as anything ’80s or prior, what’s most important to them is that their 10 different vendors (all of whom are female or nonbinary) curate accessibly priced, bright, colorful clothing, in various styles and sizes. 3022 E Burnside St

Garden Party
Best for: Dresses—no hesitation
From the dangling patchwork handbags, impressive collection of retro dresses, and tarot card–reading booth to the ever-present, rain-or-shine green shag rug and floral hand-painted sign I’d literally hang up in my room, Garden Party is clearly the must-stop-by-booth of every Portland Flea. For Onyx Baird, part-time beekeeper and now full-time clothing curator, vintage is technically anything from the ’90s or earlier—but really, she’ll source any high-quality secondhand piece that sparks joy. Baird spends three or four days a week thrifting, gravitating toward natural fibers: linens, silks, and cottons, plus modern silhouettes and bright prints. She organizes her clothing by color, so it feels like you’re stepping into a garden and “picking out the flowers you like.” Apparel is typically on the fem side, but Garden Party Fellas, a curated men’s line hand-painted on by a local artist, also dropped this summer. 3450 N Williams Ave, Suite 4