A retractable leash system includes a housing, a leash, a spool, and a brake. The spool is attached to the leash and disposed within the housing. The leash is configured to be rotationally biased so as to urge the leash into a spooled configuration. The brake includes an operating button, a compression spring, and a brake member coupled to the operating button. The brake member is associated with the compression spring and is configured to engage the spool by operation of the operating button, such that, when the brake is engaged, the spool is prevented from rotating in an unspooling direction and capable of rotating in a spooling direction.