Can I pull off the tucked in T-Shirts?

Something I've wondered, usually wear the white crew neck Kirkland T's and this raglan shirt tucked in cause I'm quite short and I've wondered if I can pull off this look or not. I feel like it doesn't look too bad, and I like an older simple look, maybe throw on a tucked flannel or corduroy shirt with the top 2 buttons undone over the T if it's chilly.