The Portland is our take on the classic Henley, also known as a Grandad Shirt or Surfer Shirt. Finished in Indigo Blue with white trim, it’s a versatile top that works just as well with jeans, shorts or chinos. The design was inspired by the shirt John Lennon wore during The Beatles’ 1965 American tour.
John wore a number of Grandad style shirts during the Beatles’ later years, but the one that inspired this top was slightly different. The rounded section at the top of the placket makes it what many people refer to as a Surfer Shirt, a style that became popular in America during the mid-1960s.
The inspiration comes from photographs taken in Portland, Oregon on 22nd August 1965, where John is wearing a similar shirt backstage at the Memorial Coliseum. He also appears to be wearing it during the press conference and when arriving off the plane. During their time in Portland, The Beatles also met up with The Beach Boys.
Why Choose The Portland
The Portland isn’t a plain Henley. The contrast Navy trim gives it a little more character while keeping the overall look clean and easy to wear. It was designed as an everyday top that works just as well with jeans as it does with chinos or shorts.
Version 3 features a slightly higher neckline following feedback from earlier versions. The result is a shape that we think sits better whether worn on its own or underneath a jacket.
What To Wear It With
The Sky Blue & Navy colour combination works particularly well with dark denim, stone or sand chinos and Navy shorts.
Footwear-wise we’d wear it with our Dewey, Mateos or Cortez shoes, although it will work with most casual suede shoes or trainers.
On cooler evenings simply throw on a lightweight jacket such as The Alf or Chuck Hoodie.
When to wear itÂ
Spring and Summer – Early Autumn – Holidays Home & Abroad – BBQs- Beer Gardens- Weekend trips away – Casual evenings out – Weekenders
Sizing
The Portland has a slim / standard 66 Clothing fit. We recommend ordering your usual size. If you prefer a more relaxed fit, consider going up one size. I wear an XL in most 66 Clothing tops and also wear an XL in the Portland. Please refer to the size guide below for full measurements.
Product Details
- 100% Cotton
- Sky Blue with Navy trim
- Henley / Grandad Shirt / Surfer Shirt styling
- Regular 66 Clothing fit
- Machine wash at 40°C maximum
- Do not tumble dry
- Cool iron
- Designed by 66 Clothing
Frequently Asked Questions
Is this a Henley or a Grandad Shirt?
Both. Different people use different names for this style. Some also refer to it as a Surfer Shirt because of the rounded shape at the top of the button placket.
Is it true to size?
Yes but its cut slightly slimmer than some of our items.
Can I wear it with shorts?
Absolutely. The Sky Blue colour makes it a good choice during the warmer months and pairs well with Navy, Stone or Khaki shorts.
How should I wash it?
Ideally Hand Wash, we have tested on a delicate wash and as a tiny amount of shrinkage. Do not tumble dry and use a cool iron.
Why do you call it a Surfer Shirt?
The rounded section at the top of the placket is often associated with Surfer Shirts that became popular in America during the mid-1960s. Depending on where you are, you may also know this style as a Henley or Grandad Shirt.

|
S
|
M
|
L
|
XL
|
2XL
|
|
| Chest |
38
|
40
|
42
|
44
|
48
|
| Pit To Pit |
19
|
20
|
21
|
22
|
24.5
|
| Drop |
24
|
24.5
|
25
|
26
|
27
|









Mateus Paul (verified owner) –
A good one for warm days! Stylish and comfortable!
Pete Smith (verified owner) –
Great shirt! Looks and feels really good. Good quality material too. Would definitely recommend buying one.
Nick (verified owner) –
A really nice shirt and quite a slim fit too which I prefer.
Any plans to make this in a different colour ?
Sean Thomas-Bouzas (verified owner) –
Another great quality, well fitting item, and here’s proof from Jan and Dean that it was indeed a Surfer Shirt!:
https://youtu.be/N5V3wcREqcI?si=iiG9oVDNP-IO4zky
Sam Cooper (verified owner) –
Absolutely perfect fit. I’m a small and it fits nice and comfortable around the arms and waist. The arms fit like a polo shirt so not baggy which I like.
Very comfortable material too. Can’t wait to give this a run out on my next night out.
David Forster (verified owner) –
I love the Portland top so much i’ve bought 2.
1 for next summer ?
Any chance of making them in a couple of different colours please.
Just a thought.
Cheers
Jeff hindle (verified owner) –
Excellent top colour slightly darker than pictures but still a great short , would buy again , I found it fits true to size .
John Howie (verified owner) –
This is a perfect shirt. The fit and detail are amazing, it’s my favorite shirt that I own. Highly recommended.
John Howie (verified owner) –
This is absolutely, 100% the perfect shirt. It has become my favorite shirt that I own. The detail and fit are perfect. Highly recommended.
Andy Allum (verified owner) –
Really pleased with my John Surfer shirt!
Nice detail with collar and button. Fantastic quality and service!!
Andy Allum (verified owner) –
Really pleased with my John Surfer Shirt.
Nice detail with the collar and buttons!!
Brilliant quality and service!!!
Steve Middleton –
Will you be restocking the Xl size ?
Andrew Lindsay (store manager) –
We will, but most properly next spring, as its summer top. And it also takes time to get them made, meaning they wouldnt be here for several months
Graeme McDonald (verified owner) –
I bought this and took out of the box andy wife went,mmmm, not sure.
I put it on and she said “wow, that’s really nice”.
The quality is excellent, and is probably one of the best t shirts I’ve ever bought. Really pleased.
David Head (verified owner) –
Love the “Portland” top. Great delivery service to Australia and customer service before I ordered.
samantha.king42 (verified owner) –
Beautifully made, so stylish and perfect fit. Bought for my son. Excellent service
Paul H (verified owner) –
Love this shirt – different from other styles but really works. Fits as sized.
Franck (verified owner) –
Excellent product. Excellent service. I’d recommend normal size.
Kevin Palmer (verified owner) –
I purchased one and liked it so much a bought a second. It’s totally fab and looks great with suede.
David Forster (verified owner) –
Chuffed to bits with my Navy Portland top.
It looks cool,ideal for the summer.
Worth every penny.
Thank you MOD SHOES
Ray Fenn (verified owner) –
Love it ??
James watson (verified owner) –
Absolutely love this fab T-shirt , I’d been looking for one similar since I saw Lennon in a picture wearing his and this one’s spot on , keep them coming guys Xx
Brad Johnson (verified owner) –
Love this shirt, but disappointed my 52 year old, white middle-aged fat ass body lets it down. Maybe this’ll inspire me to loose some weight? Probably not. If you’ve kept yourself in some semblance of healthy body weight, this shirt is tops in quality!
ellioteaston (verified owner) –
I’m from the US and grew up in the ’60’s. These ‘surfer shirts’, as we called them were amazingly popular and not just with surfers! As you can see from the photo, John Lennon even picked up on the style when he was over here in the mid-’60’s! 66 clothing have created a beautiful recreation of this shirt-and probably much better quality than the originals. This is a perfect summer shirt, and us kids that were around back then wore them “All Summer Long”! True to size so stick with your usual.
Paul Rutter (verified owner) –
Fantastic quality as per usual. Lovely attention to detail around the collar making it a great mod summer top, giving it a smart, sharp edge over your bog standard t shirt. Sizing is a tad slimmer compared to the day tripper t shirt but I’d recommend sticking to normal size. Five stars!