I really enjoy hat shops. The sales man we encountered on our two visits made our visit really…read morefun. He was so helpful and informed about hats. He was such low pressure that we were able to relax and have fun. The costs are but a fraction of what I was used to paying in San Francisco. I settled on a great, packable straw hat from Italy that I know is a keeper. My son found a great cap and is happy.

This the THE place to get the perfect hat for any occassion! Fit, style, huge selection and GREAT…read morebuying experience with the owner who is an absolute lifelong expert with hats. Don't buy crap online! Get a hat that you'll feel amazing in & spend your hard earned money at a quality local business!

I ordered the standard-sized backpack in blue. I was skeptical about ordering one, but the ads on…read moreFB wore me down. I am so glad! This is a really well thought out bag. It's so easy to pack due to the frame that keeps it open. I loaded 3 compression packing bags, my iPad, and still had room for more! And, it's not over-sized! The front clasp is appreciated to keep it in place. The color is exactly as depicted in the Portland Gear website. Generous lower front pouch too. Love this backpack!

Online clothing puchase advice:…read more I own several Portland Gear bags, but use caution when purchasing their clothing online. Think about trying to find it in the store to try it on. They are not friendly about returns. I'm sure it makes sense on the accounting side, but between shipping and returning 2 t-shirts, I'm almost $20 out-of-pocket. I rushed things and didn't take the time to go into the store because I was leaving for a trip. But they didn't ship in time for the trip and when I got back and tried them on the t-shirts were cut in a way that almost looked like mock turtlenecks. I guess the 80s are back. So leaving this here for others in case they think Portland Gear uses the same ecommerce return policies as others. If you don't like your purchase, be prepared to recoup only some of your cost.

I left a message 2+ months ago on their phone...no reply!!!!!…read more I found another FANTASTIC HABERDASHERY that actually knows what ATTENTIVE PERSONAL attention means in the business..they don't!

I was really displeased after my husband bought a walking cane here and the salesman fitted it…read morepoorly and showed him how to use it incorrectly. But after talking with the owner, we were able to get a new cane with a partial refund that I thought was fair. So I have changed my initial review from one star to four. Thank you John Helmer for your attention to your customers.

When in need of a good, sturdy "Panama" hat, this is the place to go. I visited their old location…read morein August 2025 and the current location in May 2026. Picked up a "Panama" each time! (The two I got are slightly different in style/color.)

Great selection and service finding derby hats for my husband and I! Great shop and reasonable…read moreprices!

Beautiful hats and a wonderful owner. This is one of the shops that makes Oregon City a charming…read moreplace to shop.

Love this cute shop! The proprietress was very warm, engaging and helpful. I Left with 2 everyday…read morehats, perfect for those bad hair days!

I fell in love with these hats at a local retailer and always said I had to find the store where…read morethe magic happened. No joke, one day I had a business lunch down the street and was looking for parking and found a spot right outside Flipside. I stopped in and fell even more in love. Kori was awesome and so kind. She showed me all different styles, and some new fabrics they just got and then she helped me customize my flower for a hat I had to have (loving my mustard colored flower)! I absolutely adore this store and the owners, and cannot wait to return. If you're looking for a fun, quality and totally comfortable hat (I don't get a headache with Flipside hats like I do with every other hat I've tried) you need to venture in and check it out!!!

Here are some of the reasons I loved this shop (and you will too!)…read more- The hats are really creative, cute & comfortable. - They sew the hats right here behind the retail displays - A hat for everyone. Even my non-hat-wearing husband found a hat he likes & wears! - Recycled and repurposed fabrics -yes! - Care in workmanship. The plaid in my Pendleton wool hat all lined up from seam to seam that's no accident (mom always said that was a sign of quality-she'd approve! - Kevin was super helpful & friendly. Great advice & assistance! Get here and find your own reasons to love it!

Heads up! You got a beautiful head on your shoulders? A head to hide? A bald head? A head gettin…read moretoo much sun--really, we Portland? Or a soggy PDX head? Or you just like lookin cool in cool-lookin hats. Get you head over to Pinkham's Millinery. Dayna (designer/owner) hand-makes hats from straw, rabbit fur, Nutria (like beaver), etc. for ladies and gentleman. For 34 years she's worked with all sort of heads on rock stars, actors and PDX'ers. She was commissioned by Nike to design hats for tennis greats Maria Sharapova and Serena Williams. Heads up! Neck, shoulders, eyes, hair, etc.--all considered in custom hat design that fits your character. Each hat (brim & crown) fits well--made well--in Dayna's workshop & boutique. I dropped in and Danya starting checking-out my noggin and showing me materials in various shapes and colors that work with my zany character. I like rabbit fur. Even if you don't need a hat now, it is worth knowing about now! Hat making is fascinating and Danya loves (knows) hat-talk! No selling! Danya said "go home and think about it." What style of hat do I want? You will have a Pinkham hat for a life-time! Guaranteed to fit for as long as you have a head on your shoulders! And Danya is still kicking! And she will re-shape a hat anytime you like--years later! It takes 2 weeks from design to new hat-on-the-PDX-streets! Nobody has a head like you! Nobody should have a hat like you! Heads up! Put a lid on it!

Truly beautiful handcrafted hats! This shop is half showroom, half studio workshop and so it's…read morereally fascinating to get a glimpse of all the hat blocks and supplies that go into the artistry of these headpieces. You'll find an array of wool and straw hats for men and women, as well stunning on-of-a-kind fascinators made from feathers and taxidermy birds. The proprietor, Dayna Pinkham, is lovely and was happy to let us try on pieces that struck our fancy, and even recommended a lovely wool felt hat that really flattered my face shape. Sadly, being out of a job meant that I wasn't able to purchase it (this sort of quality doesn't come cheap, but is still much more affordable than milliners in LA) but she wrote down the style, size, and various options so I can phone order a custom one when I'm ready to purchase.

Difficult to find the place and it was closed, wasted 30 mile drive. Looked like the place was…read moreabandoned.

Historically, I've been pretty careful about ordering hats online because I like to try them on…read morebefore buying. I came across Penman Hats while looking to replace a well-worn much beloved fedora that was unfortunately lost. Intrigued by the idea that all of the hats offered are made by hand, by the owner himself, and the fact that many well known folks wear his creations, I went ahead and ordered a whisky colored beaver felt with an iron colored vintage ribbon. Not long after, I received the package and when I opened it I was as pleased as I could possibly have been. Besides the hat itself being a work of art, every detail of the packaging was a delight. The hat came carefully wrapped in a plastic outer bag to protect it in transit. It had been placed in a very high quality hatbox with a gold embossed logo closed with a with silk cord. Inside the box were tags that could be filled out and kept in the hat in case it was lost (wish I had this for the one I was replacing), an enamel lapel pin that found it's way to my lucky backpack and of course the hat itself. The hat was flawless. It has a 5 point bash, and is carefully stitched all around. The interior is silk lined, and has a leather inner sweatband meticulously hand stitched on. Most importantly, the fit was exactly as measured. I highly recommend following the instructions that the company has online for finding your correct size; they don't use generic sizes like M-L-XL and the hats are all the better for it. If you're looking for a quality hat, made by a master hatter using old-world craftsmanship, you can't go wrong ordering one of these hats.

Fantastic store. Friendly staff. The Portland Outdoor Store is an amazing resource, and should be…read morecommended for sticking with it for 100 years.

I was so boring, nothing but shoes and cowboy stuff, nothing of value, it was all cheap stuff for…read morehigh prices, service honestly sucked, no came when I needed help this place sucked.

This store was as good as its reputation, filled with amazing collection of Portland souvenir…read moregoods, stationary items, apparels and local made food products. The store was clean and organized. The prices of the items were comparable to other shops we had visited in and around Portland. Among the products, I loved their magnet wall full of unique designs. There were really nice stickers and postcards. After exploring the store for several minutes, we picked few magnets and stickers. Staff members were friendly and interacting with guests. The checkout was quick and easy. Highly recommend this store to anyone looking to do souvenir shopping in downtown Portland.

I did a quick search for any type of souvenir store to find some Portland themed gifts and quickly…read morecame across this one. They have a nice location right by Powell's Books so it was a nice way to hit two birds with one stone. Everything in this shop made for a great gift, from stationary to stickers to apparel for all ages, and even Portland themed children's books. The staff were super friendly and helped look in the back to get me more sizes in the children's shirts. This was a nice stop for souvenirs without paying airport prices.