Kasey Jackson of Freestyle Superette. Photo by Emily Rogers.

Counterculture Couture

Vintage stores provide a portal back to the early years of the Oregon Country Fair

The summer of 1969 marked key events in history from the first man landing on the moon to Woodstock, and the beginning of the Oregon Country Fair. 

Longtime fairgoers will tell you that one of the things you should bring to the Fair is a fun costume. Vintage stores on West 5th Avenue and 13th Avenue such as Bumble Boutique, Freestyle Superette and Wild Paisley are curating Fair looks from their “true vintage” collections. 

True vintage fashion includes clothes that are from the ’70s and earlier. These retro styles can pay homage to the year when the Fair first started, or be styled in a modern fashion to provide customers with an individualistic look. 

As a fellow vintage store employee, I know firsthand the meticulous effort required to find vintage clothes that cater to all shapes, sizes and occasions.

Bumble Boutique 

233 W. 5th Avenue, 541-735-3198


The owner of Bumble Boutique, Sarah Hambrick, is a native from Veneta. Hambrick recalls hearing the drums from her bedroom window in the middle of the night and thinking to herself that she couldn’t wait to see what was happening at the Fair. Now having gone to OCF many times herself, she sources clothes for the event. 

Six weeks before the Fair, customers start coming in to plan their Fair outfit, according to Hambrick. When sourcing for OCF, Hambrick says, “I look for textural, colorful, playful pieces that can be put together creatively such as petticoats, corsets, fairy-like dresses, flowy skirts, small tops, breathable fabrics, lacy bloomers and, of course, accessories.”

Hambrick’s current favorite OCF outfit in the store is inspired by the bold looks in Alice in Wonderland. The outfit includes an extra-full petticoat with a feather bustle ribbon belt accessory, a corset top — all accessorized with a rhinestone choker necklace and a mini top hat.

For an extra added flare Hambrick believes no Fair outfit is complete without body glitter. 

Freestyle Superette 

37 W. 13th Avenue, Unit 205, 215-681-8515


Sitting at the corner on the second story above Big City Gamin’ is Freestyle Superette, a vintage store with items ranging from UO Duck gear to ’60s homemade dresses. 

Freestyle Superette owner Kasey Jackson has been putting together outfits for the OCF since early May. Jackson has many returning customers who are OCF veterans or OCF workers who come to her to source a unique look. 

Among Jackson’s collection are handmade performance outfits from a “snake oil salesman” and ringleader performer at the OCF in the late ’70s and early ’80s. The looks consist of vintage suits embellished with vintage pins, tassels and sashes. 

“No matter what, a vintage store or a secondhand shop,” Jackson says, “you’re probably not going to show up in the same thing that everyone else has.” Each of these pieces is one of one, which is something that Jackson considers a pull for those going to Fair. 

“Fair allows people to wear their personality on the outside,” Jackson says, and individualistic clothes are a part of that. 

Wild Paisley

37 W. 13th Avenue, Unit 203. 828-242-2961


Wild Paisley is located next to Freestyle Superette, and with a wall of bright smiley faces and tags created out of pictures of Woodstock, the store takes you back to the eccentric time of the late ’60s and early ’70s. 

According to owner Eugenia Borkowski-Sypherd, the two stores complement each other. “I do some things that she doesn’t, like, the silly costume accessories I’m starting to build up, and she does a lot of vintage sportswear, which is not my forte,” Borkowski-Sypherd says. 

This sentiment aligns with Borkowski-Sypherd’s advice for fair goers “If you aren’t wearing something outrageous, you’re going to regret it.”

Her favorite Fair outfit that she’s curated was centered around a pair of fairy wings a customer was wearing. The outfit was completely styled with pieces in the store, including a 1960s white baby doll nightie, bloomers, ruffle socks and a pair of mary janes.

To have the best time at the Fair these three owners advise to wear your personality on the outside, and bring sunblock.