First things first, creating a billowy look is surprisingly easy. You just need a loose fitting top. I like to size up for an over-sized look. I'm a bit "bigger" on my bottom (Thank you for that Francis Ass) so I compensate by getting a shirt that is at least a medium or bigger. The blue striped shirt pictured above is actually an XL, which I didn't figure out until I purchased it and took home from TJ Maxx.
From there I simply roll my sleeves up, and I don't really care about getting both of them super symmetrical, as it's meant to look a little "lived in" and casual. This shirt also came with a couple of cuff bands that I can't quite get myself to cut off just yet, although they're more of a nuisance than anything else at this point. Like I said, It is suuuuuper easy going, but if I wanted something a bit more polished then I would definitely take the time to measure and iron out a J-Crew type cuff.
Obviously, I couldn't find an exact shirt from the look I shot, because lol TJ Maxx. However, I did collect some of similar styled tops that would give the same billowy oversized affect that I adore so much. I also tried to keep it under $50 (with the exception of 1) to make it affordable!!
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