10. Knit Vest over an Oversized Button-Down
The sweater vest trend shows no signs of slowing down, and it is the absolute champion of transitional layering. Wearing a chunky knit vest over a crisp, oversized white button-down shirt allows you to play with proportions while staying warm. The collar and cuffs of the shirt peeking out add a preppy, polished structure to the look, while the sleeveless knit keeps your torso cozy without the bulk of full sleeves. Pair this combination with tailored leather leggings or slim-fit trousers and loafers for a smart, academic-inspired outfit.