Shopping Portland | Winn Perry


Every trip to the Pacific Northwest for at least the past five years has included the same thought: “I really want to check out Winn Perry.”

This classic men’s store opened its doors originally in 2008 (it moved locations and went on a brief hiatus at one point), but it has reemerged better than ever and still carries Alden and a variety of other finely made things. Looking back I can’t figure out if it was either right on time, or slightly ahead of its time. Though, I can say that it is about time that I actually made it in for a visit in real life.

Winn Perry has always been understated and restrained in a good way. It wasn’t chasing a trend or movement, it was just focused on stocking good things that will last a long time. Walk in and talk to the store’s owner Jordan Sayler (he’s also the buyer and all-around shopkeeper) who can speak in great detail to everything in the place. Have a question about fit or quality? He can answer it. There are many stores these days that can actually do that, but the good service at Winn Perry is an enjoyable (seemingly throwback) experience nonetheless.


The shop has a solid core group of brands on offer: shirts from New England Shirt Co., handsewn shoes from Rancourt, a great selection from Alden, bags from Archival Clothing, goods from Levi’s Vintage Clothing and a lot of small items like American Optical sunglasses, Proraso grooming products and pocket knives from Bear & Son. Stores often over complicate things with the amount of brands and product mix. At Winn Perry the opposite is true. There’s an over-riding simplicity to the space, the merchandise and to the ambiance. It’s saying: “Everything you need, nothing you don’t.” Only it doesn’t have to say it. It doesn’t need to be overt and obvious the way a lot of new stores do. And what’s there is good. Pure and simple.

Do yourself a favor and don’t be like me and take five years to visit and figure it out. [WINN PERRY]



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Winn Perry | 209 SW 9th Ave. Portland, OR 97205 | (503) 664-4317

Comments on “Shopping Portland | Winn Perry

    Cory on July 30, 2014 2:06 PM:

    Looks like a must-see next time I am in Portland. I wish I had known about it before…

    marc on July 30, 2014 4:10 PM:

    Hey guys – I know you love Portland. There are so many great stores for men in Portland, OR probably more privately owned men’s shops (or close to it) per capita than any other city in the states.

    I too love Winn Perry, Machus, Lizard Lounge and then there is Michael Allen’s. When I first saw the shop, I was ready to pass it by – then I saw these 2 beautiful King Charles Spaniels running around the shop so I had to go in.

    I find that the owner and buyers have a great perspective on the “modern man’s” lifestyle. It’s contemporary without being trendy, funny as a NYC’er I always seem to buy something there.

    Go check it out and let me know what you think!

    Lesli Larson on July 30, 2014 4:47 PM:

    Jordan is tops. I’m currently obsessed with Jordan’s Abbeyhorn accessories – especially the key fob. Best gift ever!

    Gretchen Harmon on July 30, 2014 8:35 PM:

    AND don’t forget – in Oregon – there’s NO sales tax!

    toad on July 31, 2014 1:59 PM:

    Dude, seriously, do you spend your life just going around buying stuff you don’t really need? Inquiringly yours…

    Paul on August 1, 2014 10:56 AM:

    Marc-I can only assume you work for MIchael Allen’s “Clothiere” after reading your post. There is nothing similar about that store and WP. The salespeople are pretentious as is the owner. MA is where a 45 year old goes to buy euro shirts for clubbing. Oh that’s right you sell Barbour which makes it like WP? No. Visitors of Portland, you’re better off shopping at the Rack before MA. Unless you’re looking for an 8000 dollar bespoke suit that comes with complimentary Pinot noir at the fitting.

    Toad- do you spend your life making absurd comments on blogs that don’t need to be made?

    Bebe on August 1, 2014 11:36 AM:

    Always good to see a store that carries my shaving brand: Musgo Real.

    Matthew Pike on August 1, 2014 12:15 PM:

    Looks pretty top and a nice mix of brands too, I for one would go for the service and chat alone as it sounds spot on.

    Buckets & Spades

    Chris.R. on August 1, 2014 5:46 PM:

    Michael, I love the way you take your photographs. You always make me want the things I see.

    The store looks great too, “Pure and simple” and the quality comes through the photos.

    Mike B. on August 2, 2014 2:01 PM:

    I visited Winn Perry a few months ago and was lucky enough to stumble upon the store empty, which meant Jordan could patiently walk me through his offerings. He’s modest, knowledgable and shows a sincere interest in the items he stocks. It helps that he’s not assertive, preferring to let the items sell themselves (which they did.) I’m happy to support owners like Jordan, and stores like Winn Perry, that serve as a ballast to some of today’s more aggressive and fashionable retail offerings.

    Also, be sure to inquire about the namesake of the store for a brief, but charming story.

    Steven on August 5, 2014 10:20 AM:

    @Paul – You’re on the money about Michael Allen. I’m a local Portlander and this place is absolutely ridiculous. The majority of their clothing selection is gawdy and disgustingly over-priced. I’ve been in several times and each time I’ve had an unpleasant experience with the stuck-up owner or one of his greater-than-thou #menswear on coke salespeople. When in Portland, skip Michael Allen and head to Winn Perry. Jordan is good people and his shop is wonderful.

    John on August 7, 2014 5:52 PM:

    I just dropped by since I was in the area from the SF Bay Area for a day. The selection is ridiculously small (nice selection of Alden and Rancourt shoes, about a dozen different shirts 2 jackets, literally one style of pants in three colors and then the accessories mentioned in the article). But what is there is pretty excellent. I’m an Alden man, plus New England shirts is my go-to brand. Bought a great sweatshirt, locally made, reasonably priced.

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