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    Classic Collection

    4.3 (22 reviews)
    ModerateHats
    Closed 10:00 am - 5:00 pm

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    Hats on tables
    John K.

    I spent far too many years of my life being ignorant of the benefits of a good hat. Thanks to Classic Collection, I've now got a warm waterproof model for winters, and a ventilated lightweight version for summer. In both cases, the rain never hits my glasses or my neck, and the sun is never in my eyes. They have lots of styles, and, despite having an oversized head, they've got lots of things that fit me well. My most recent trip was with a visiting friend who asked me where I got my hat, and had to make this a part of his visit to Portland.

    My cool brown bowler.
    Alan S.

    Their website simple doesn't do them justice. Every inch is filled with a huge solution of men's and women's hats in about every shape, style and color imaginable. I had been shopping online and saw a hat I was very interested in, however I was reluctant to order from a picture at someone's website. I wasn't sure of the size and actual color let alone how I'd look wearing the hat. I was very pleased with the options of the style I was interested in at Classic Hats on Hawthorne. Not only was I able to touch, try on and admire the hats I'd only seen pictures of online, I know I saves money shopping local. The hat I bought was a brown bowler for a dollar more that the base price online, and I'd still have to pay for shipping online. The staff was very friendly and helpful. For anyone looking for a hat of any kind, I highly recommend that you swing by this shop and compare what you might see at someone's website. I look forward to shopping again at Classic Hats.

    Classic Collection - Portland, OR

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    28 days ago

    Great selection and service finding derby hats for my husband and I! Great shop and reasonable prices!

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    11 years ago

    This is for the Downtown location: Offensive, intrusive, insulting saleswoman.

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    Ask the Community - Classic Collection

    Review Highlights - Classic Collection

    I don't have much money, so while I wish I could walk into John Helmer and drop $150 on a fedora, I had to find an alternative.

    Mentioned in 2 reviews

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    Flipside Hats - Marco models the original reversible Ptown cap.

    Flipside Hats

    4.5(15 reviews)
    2.3 miMontavilla, Southeast Portland
    $$

    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!

    Photos
    Flipside Hats - Emily Models The Pearl Cap . http://www.flipsidehats.com/magento/hats/styles/pearl.html

    Emily Models The Pearl Cap . http://www.flipsidehats.com/magento/hats/styles/pearl.html

    Flipside Hats - Connie models the Sunhat. http://www.flipsidehats.com/magento/hats/styles/sunhat.html

    Connie models the Sunhat. http://www.flipsidehats.com/magento/hats/styles/sunhat.html

    Flipside Hats - Sera sports the Eco Visor. http://www.flipsidehats.com/magento/hats/styles/marathon-visor.html

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    Sera sports the Eco Visor. http://www.flipsidehats.com/magento/hats/styles/marathon-visor.html

    Pinkham Millinery

    Pinkham Millinery

    5.0(8 reviews)
    2.7 miDowntown, Southwest Portland
    $$$

    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.

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    Pinkham Millinery
    Pinkham Millinery
    Pinkham Millinery

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    The Penman hat company - Happy new year from www.penmanhats.com let's start the year off with a customer of the week. #OnlyPenman #penmanhats

    The Penman hat company

    3.7(3 reviews)
    17.4 mi

    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.

    Photos
    The Penman hat company - Customer of the week @penmanhats #fedora #hat #hatter the finest in #bespoke #penmanhats #OnlyPenman

    Customer of the week @penmanhats #fedora #hat #hatter the finest in #bespoke #penmanhats #OnlyPenman

    The Penman hat company - Ah, the good life. @karlurban  looking relaxed in his #penmanhats 
If you haven't seen him in #thorragnarok you owe it to yourself.

    Ah, the good life. @karlurban looking relaxed in his #penmanhats If you haven't seen him in #thorragnarok you owe it to yourself.

    The Penman hat company - Just finished this Indy 4 train travel hat. #OnlyPenman #penmanhats

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    Just finished this Indy 4 train travel hat. #OnlyPenman #penmanhats

    Classic Collection - hats - Updated May 2026

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