I love items that have an air of whimsy about them, but when we’re talking fashion, there’s a fine line between what’s whimsical and wearable as opposed to cartoonish and comedic. To steer yourself in the right direction, think in terms of playful, unexpected—even slightly amusing—details. Perhaps it’s the juxtaposition of one exaggerated feature on an otherwise simple dress; a delightfully eccentric decoration on some furnishings; or an imaginative color combination on a utilitarian object that you find appealing. Whatever it is, it should tickle your fancy just enough to make you smile.

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