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I am not a guy however, I am married to a guy and my personal preference is tucked in, especially if we are going to supper.
His personal preference is he doesn't care and will tuck in when we are going out to supper just for me.
It depends on the shirt. A guayabera is meant to be worn untucked. Hawaiians and other tropical-design shirts can be left untucked, especially the designer-type ones.
I always tuck in my shirts, T shirts, and tanks. It makes me look slimmer, and the belt + shirt helps my pants stay up.
My waist size is 33.1", so size 34 is too loose but size 32 is too tight. I keep my pants up by fully tightening 34 belt + Tucking in the shirt.
They're harder to find, but they do make 33's in waist for pants. I have a similar problem though, think I'm also around 33, just depends on the pant type, sometimes I can swing a 34 sometimes I can't.
I'm not finding an exact definition for "casual shirt".
Anyhow, my personal "rules" are:
-don't tuck t-shirts (when worn as an outer shirt)
collared shirts:
-with sneakers, don't tuck
-if wearing any kind of dress shoe or similar, tuck regardless of pants
-with any kind of dressy pants, always tuck (exceptions: guayaberas and similar short sleeved shirts)
Casual shirts with straight hem and slit - ok to wear out. Everything else - in.
33 jeans are on the market. Almost every cleaner has an alteration person to put two darts in a 34 waist so a cinched belt does not make jeans look like a ruffled skirt. Try it yourself - needle and thread are available at the $-store.
It depends on the rest of the outfit and the season. In the fall or winter when I'm wearing things such as leather boots, cords, jeans, or winter-chinos with thicker buttonups I tend to tuck my shirts in more and also tend to button the shirts up more.
In the summer when I'm going for that stylish but breezy look that I'm pairing with slip-ons (not boat shoes), chucks, nice sneakers and summer-weight jeans or chinos, I more often than not leave the shirts untucked and leave a few extra buttons undone at the top.
So for me it really depends on the event/location, the season, and the whole outfit. Either one works depending on the combination of those factors.
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