Billowy Shirts?

[SolomonMarlow]

I've always been fascinated by a good billowy shirt. When do they look good? When do they look bad? I feel like every time I try to pull one off, it doesn't tuck quite right--the tuck looks more rumpled and ruffled than properly billow and full (I am tucking into high waisted pants, fwiw). Any recommendations for a good billowy shirt, or how to pull one off? (Last few photos are me.)

PS: how do the shoulders fit? I bought the shirt a long while ago as an intentionally oversized shirt, but I think I'm going to size down on the next one....

 

[Club Soda]

I feel like a shirt needs to be cut straight to achieve this and wearing a tailored shirt sized up may not have the right effect. The first photo shows how square the body of the shirt is. The fullness has a clean line that falls from shoulder to the waist where it's tucked in.

My Drake's ocbds are my primary rotation. I feel they're a true regular fit that tucks in well and has the right amount of comfortable room. Polo OCBDs in my opinion are one the best fitting because they fit very full in the body but the sleeves are actually pretty tailored so it looks intentional. I'd wear them more if they had a better collar.