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You certainly won't freeze to death if that's what you want to know. So, in that sense, yes it's warm enough to wear shorts and a t-shirt 24/7 365 days a year.
But, at this moment in Wahiawa, as an example, it's 64 degrees (and it was cooler overnight), while it's 69 degrees by me in Honolulu (rain is definitely keeping things cooler as well). I wouldn't wear shorts and a t-shirt in this weather, but that's me. It's a bit too nippy for me, but I certainly see people wearing shorts and t-shirts in this weather. All of this is to say that it'll be up to individual preference and limits.
If I'm on island and don't have an event that requires me to be dressed up - I'll be found in shorts and a short sleeve shirt (not a t-shirt) all year round.
Really depends on the person as I see plenty of people with jackets in the winter months, especially when raining, but also plenty in just shorts and t shirts. As for me in 40+ years of living here I can't recall ever wearing a jacket or anything else to keep me warm. I just doesn't get cold enough for me to wear anything. Only exceptions would be when me and my family would drive up Haleakala on Maui as a kid.
A lot depends on where on the island you expect to be. Windward side is generally windier, rainier, and cooler. Leeward coast and down the south shore, typically sunnier, warmer, sporadic very light showers if any. Higher elevations, like Makakilo, and inland...Mililani, Wahiawa, cooler and more rain.
Originally from the midwest, I only wear shorts and t-shirt outside of working hours, although I do keep a long sleeved sweat shirt in the car in case I end up on the windward side with strong trades. Flip side is, over 20 years here, I close my lanai doors maybe 6 or 8 nights out of a year due to cold and/or strong winds; and maybe turn on the AC fewer than a dozen nights per year due to Kona winds and/or humidity (or very occasional VOG).
Windward side is generally windier, rainier, and cooler.
During winter, the windward side, specifically at night, is typically a few degrees warmer than the rest of the island when trade winds are occurring due to the temperature of the ocean.
At elevation, yes. On the coast in some places, you'll want air conditioning.....but then there's a hefty price in your electrical bill.
There can be a big difference in climate in two places just ten miles apart.
Oahu or any of the Hawaiian Islands are not as tropical as places like Guam,The Northern Mariana Islands,Puerto Rico,American Samoa,The U.S Virgin Islands when it comes to temperatures.
The lowlands of Oahu dip into the 60's during the winter months and sometimes the 50's,then you also get the Kona Low which is a Cold Core Storm System and you rarely get any hurricanes in the Hawaiian Islands because of the cooler ocean temperatures.
On Oahu and on any of the Hawaiian Islands,it does experience cooler to colder temps at Higher Elevations.
When I lived in Guam and I first went to Oahu in December and was outside it literally felt like being in an Air Conditioned Room at night when the trade winds were blowing. I never been on a tropical island with such cool air temperatures.
In other words you'll need a light sweater/jacket if your in Hawaii during the Winter months,especially for the evenings unless temps in the 60's are warm for you,but remember the higher up you go in elevation the temps do get cooler to colder there,all depending on how high up you go.
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