Hawaiian vacation wardrobe from nothing

[malligator]

Quick background: middle-aged guy, reasonably decent shape, just started really caring about my clothes a few years ago, live in the PNW so relatively new wardrobe is biased toward cool weather, generally dress up Trad and dress down Workwear

Okay, now that that's out of the way...the last time I went on a tropical vacation was in '19 before covid and I was still rocking board shorts, t shirts, Patagonia long sleeve sun shirts, etc. Now that we're free to move again we are headed to Hawaii and I want to dress better without completely going against the laid back island style of Hawaii.

My thoughts:

Shoes: flip flops (beach and pool), espadrilles (during the day when not around water), boat shoes (evenings)
Pants: swim trunks, cotton shorts, a pair of chinos, a pair of white linen pants
Shirts: a few aloha shirts, long sleeve seersucker button up, OCBD(s), maybe some non-aloha camp shirts
Hiking: pants/shirt/shoes specifically for day hiking

Basically, I'm trying to move up from the 'surfer' territory I've relied on since I was a teenager in the 80's, but not move into 'dad' territory--if that makes sense.

 

[breakaway01]

Sounds pretty reasonable.
A few thoughts:
In terms of trousers, I’d skew casual in styling—so something closer to RRL or Wallace and Barnes for chinos, a more relaxed cut rather than a very tailored look for the linen trousers. Consider cream instead of white.
for shirts, true OCBDs wear hot. Camp collar shirts are great. Maybe a linen shirt or two.Consider buying an aloha shirt when you’re actually in Hawaii? Unless you already have one.
Have a great trip!

 

[malligator]

I appreciate it.

I agree about the OCBDs. I think I'll add some more short sleeves and leave the OCBD at home.

I've bought a few aloha shirts already from what seem to be authentic Hawaiian brands--Tori Richards and Kahala.

My linens are definitely a relaxed cut.

 

[johng70]

Regarding shirts - linen shirts are my favorite for tropical climates - very breathable. I would also add this: don't try to mix your casual wardrobe and your hiking wardrobe. For hiking, function wins out - get real hiking boots/shoes from an outdoor company. My northface shoes and Asolo boots are much better at hiking than any of the expensive shoe brands I wear for casual. It's also where I might also utilize more technical pants - with removable legs - long sleeves and long legs have advantages depending on terrain and bugs. So, my hiking gear is chosen because of it's function but I wouldn't wear it out any other place.

For casual wear - linen or silk button downs - camp style shirts are great but so are other shirts as long as they're designed to be un-tucked.

For beach and ultra casual - get yourself a pair of Olukai flip-flops. Better arch support than some shoes.
Outside of hiking, I suggest cotton shorts. I also suggest that with shorts, untucked shirts look better - so linen or silk button-downs designed to be untucked will look good AND be comfortable.

General footwear: with casual shorts/shirt loafers look great. Have fun!