Portland’s West End isn’t what it once was. Whereas an unfortunate dearth of local menswear shops once characterized the bustling downtown district, a bevy of dapper and high-quality retail stores have blossomed amid the city’s growing thirst for locally-sourced and American-made goods. Spruce Apothecary and Danner, Oregon’s iconic foot brand, both recently-opened shops in downtown’s Union Way. Poler and leather-toting Tanner Goods followed in suite, and the classically like-minded Self Edge wasn’t far behind. However, Winn Perry & Co. was a different kind of dapper before co-owner Jordan Sayler closed its doors in 2011 to pursue a merchandising and product development job elsewhere. It was one of the first Portland stores to feature remarkable craftsmanship specifically catered toward the value-conscious man who opts for quality over quantity, and one of the few to bring a classically-elegant approach to fashion into the modern era. And fortunately for Portland, Winn Perry & Co. is once again open for business — this time west of the dividing Willamette River and a mere stone’s throw from the aforementioned retailers.
Nestled between a juice bar and one of Portland’s landmark record stores, the new location is much like the living room you never had. The space is compact and sparse, delicately highlighted with a handpicked selection of homemade furniture and a collection of beautiful canes culled from business partner Kurt Foster’s personal collection, or more so his grandfather’s. Levi’s Vintage Clothing denim and a range of Alden shoes dapple the left-hand wall, while a healthy assortment of Tory Leather belts and handcrafted accessories — Bear & Son pocketknives, Abbeyhorn oxhorn tumblers, English Hunter’s Flasks, etc. — litter the center table. Other classical-tuned and tasteful apparel adorns the shelves, including a swath of custom, 7-oz cotton jerseys that are knit, cut, and sewn locally by the last remaining cotton knitting mill in Portland (Columbiaknit). Like the store’s custom-specified oxford shirts and flannel, the crews are reliably crafted with special attention to detail, sporting double-needle stitching and a taped jersey neck for added durability. Elsewhere in the store, a vinyl record player basks beneath a hand-carved cuckoo clock, readily poised to blast Creedence Clearwater Revival’s Green River or Johnny Cash’s Orange Blossom Special (two of Sayler’s favorites at the moment).
The Manual recently sat down with 28-year-old Sayler to discuss his fashion philosophy, his new brick-and-mortar store, and what the future of Winn Perry & Co. holds for the Portland native.
The Manual: How did Winn Perry & Co. originally begin?
Jordan Sayler: We originally opened in 2008 on the east side of Portland. We shared a space with Duchess at the time, a retailer specializing in custom clothing and wedding apparel, so the original idea was to supply off-the-rack clothing — belts, shoes, shirts, etc. — to go hand-in-hand with the custom suiting. We shared the building with Duchess for two years, before we moved next door into a small space and I began to venture out on my own. I then closed the store in 2011 to take a job with Schoolhouse Electric, retailing out some of the old merchandise online for awhile before shifting my focus to other things.
M: So, why reopen now?
JS: There wasn’t any one, “aha” moment. Kurt and I had been discussing things to do together for a long time since we were both involved in clothing and I was still in contact with a lot of my old vendors — many of whom I had made friendships with were continually pressing me to open the store back up so they could have someone in Portland. From there, it organically grew into something new, something reliant on conversations between Kurt and I and what we wanted to do. It just seemed like the right time. [Note: Foster is currently the Senior Global Merchandiser at New Zealand-based apparel company, Icebreaker, and has been so for the past six years].
M: How did you originally get involved in men’s style and fashion?
JS: While at Portland State University, I did the stereotypical Portland thing: I screen printed out of my garage. I screen printed a lot of things, but mostly band t-shirts and those for coffee shops. Between screen printing and doing a little graphic design work on the side using Adobe Illustrator, I just began garnering a greater interest in quality clothing. Local production and products made in the U.S. have always been appealing to me. You can get quality goods anywhere, but I’ve always been personally interested in supporting the people closest to me (or as close as possible). The United States has been an important manufacturer over the last 150 years and I believe it’s important to keep that tradition alive in some regard, even if we’re not always the bastion of apparel manufacturing we once were. It’s an important skill set to keep within our country, so I try to work with U.S. manufactures and product whenever possible. It’s just something that’s always made sense in my head.
M: What’s the main thread underlying Winn Perry & Co.’s stock?
JS: We strive for high-quality, well-made menswear people can love and hold on to for a long time in their closet. We don’t believe in disposable goods, and we try to take an updated sensibility to classic garments, whether it’s tailored for a man who is 18 years old or 70. We have a specific taste catered to the Pacific Northwest and the climate. We do special make-ups on our shoes [styles made exclusively for individual retailers] so they’re built to last if they get wet, and because Portland rarely exhibits extreme seasons, most of our garments can be comfortably worn fall through summer. You can see a guy wearing jeans and a nice shirt four seasons of the year. Flannel may change into a broadcloth or a poplin blend, but as far as clothing clothes, you can keep the same things year round.
M: How has the Portland’s fashion scene changed over the past few years?
JS: Well, there’s been a greater interest in men taking more care regarding the things they’re wearing. They want to be more knowledgeable, they want to take more thought about who’s producing the things they buy and where the apparel is coming from. When it comes to lifestyle brands, it’s not so much about the product as it is the values beyond it, from the production to the story behind it. In my mind, lifestyle is more in regard to the values and everything that’s involved with that actual company. And people can relate to that.
M: What are some of your favorite items in the store?
JS: I’m always incredibly partial to the Alden shoes, but that’s always been a favorite of mine. However, the thing nearest and dearest to my heart — because I had a hand in every part of its production — is the custom-made t-shirts we make. We design the fit and styling of the entire garment, and the fabric and constriction is developed and made right here in Portland. I wear them everyday.
M: What’s next for Winn Perry & Co.?
JS: We’re definitely going to be rounding out our merchandise selection for the fall, but as far as clothing is concerned, we hope to add more outerwear and knitwear. I’d also love to start doing more local production of our own items, opposed to relying on local and national manufacturers, starting with belts and wallets. It may be a but further down the line, but that’s something I enjoy doing.
Check out the Winn Perry & Co. website for further information and to shop online — or if in Portland — head over the shop’s brick-and-mortar store on SW 9th Ave., directly off W. Burnside.
