rakishly

Rakishly is an adverb that describes a manner of acting or appearing that is dashing, jaunty, or boldly unconventional. It suggests a certain swagger or confident, often slightly rebellious, attitude. When something is done or described as rakishly, it implies a departure from the ordinary or the staid, often with a hint of charm or attractive disarray.

For example, a man might wear his hat rakishly tilted to one side, indicating a carefree and stylish disposition. A smile could be described as rakishly knowing, suggesting a playful and perhaps mischievous understanding. The term often carries connotations of a bohemian or adventurous spirit, someone who doesn't adhere strictly to conventional norms. It’s not necessarily about being sloppy, but rather about possessing a confident, individualistic flair that draws attention. The word can be applied to a person's appearance, their demeanor, or even the way an object is positioned. Ultimately, "rakishly" conveys a sense of energetic, unconventional attractiveness.