To anyone under sixty it means: a kid who failed the university entrance exam.

What a Japanese person actually thinks
This is the reading everyone reaches for first, because it's a fact of ordinary life — every family has a 浪人 story. Wearing it says 'I flunked my exams' far more loudly than 'I answer to no lord'.

Meaning

Literally: wave + person
Actually: Historically, a masterless samurai. In modern Japanese, overwhelmingly: a student who failed their university entrance exams and is spending a year cramming to retake them.

Scores

Naturalness●●●●●

Very common current word, with a meaning that has completely displaced the historical one.

Coolness●●●●●

The characters are attractive. The modern meaning is fatal to the romance.

Watch out

high浪人生 (rōninsei) is standard vocabulary in every Japanese household. The exam-failure reading is not obscure — it is the default.

Get this instead

風来坊 fūraibō
a drifter who goes where the wind takes him

The wandering, unattached romance you actually wanted, with no exam associations.
無宿 mushuku
without a registered home; an outcast wanderer

The Edo-period term for someone off the register entirely. Genuinely evocative of the masterless life.

On skin

浪人

Orientation: vertical

N/A — reconsider the word.