Will this make me look incredibly hot?...again?

Yes if worn during summer , you will look and feel very hot🤣

Does it shrink enough in the dryer to justify buying one size larger than usual?

I'm usually in between a medium and a large. When I first tried it on before washing it, it definitely was a tad big but now it fits perfectly after 2-3 washes. It will definitely shrink a bit so you should be safe to get one size bigger!

I love Henley's but want buy any unless the "banded sleeves" will hold the sleeve tight at wrist and not let it slide down on my hand. Is this tight?

I bought two of these shirts for my nephew and son in law to take to Montana. Looking at my review, the shirt that fit my nephew has tighter sleeves but my son in laws is looser in the cuff. Look for my review and see my photos. I ordered 2 sizes larger for the black shirt and its loose. It might have shrank. It all depends on how you order the shirt to fit, on my nephew the sleeves do not hang down. It was a nice quality shirt and at the time so affordable. Wet the sleeve and dry it to shrink if you have too:)

how is the length on the medium?

The length is perfect for the sizes medium and large they fall below the belt

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