Style Fan, yes, I remember seeing Style Bee's post on the Tradlands sweater and thinking, "there's no way that sweater would stay semi-tucked into my jeans all day." In general I find her reviews very helpful since we're a similar age, size, and complexion, and I love her style.
FashIntern, I'm happy to tuck in just about anything -- tees, shirts, turtlenecks. I almost always tuck my ribbed turtlenecks because they're fitted and look weird sitting on top of the fly. It's when I see knitwear with a fair amount of bulk tucked in that I roll my eyes a little. It just looks uncomfortable and unnecessary to me.
Sal, you hit the nail on the head! It's the layers. If I'm wearing a sweater, it's an outer layer with a tee /tank/cami underneath, or sometimes a shirt. Having multiple layers tucked seems like a hassle.
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