Messy Bun with a Headband

It depends on the occasion. For everyday casual wear, a simple elastic, fabric, or thin metallic headband works beautifully. For special occasions, jeweled, beaded, or embellished headbands elevate the look. For workouts, thick stretchy sport headbands are ideal. Avoid headbands that are too tight and give you a headache, or too loose and slide off. The headband should stay in place comfortably without constant readjustment.

You need enough length to gather your hair into some kind of bun, so chin-length is the minimum. On shorter hair, the bun will be very small, which can actually look adorable and proportionate with a thin headband. You may need extra bobby pins to secure shorter layers that escape the bun. If your hair is too short for a full bun, twist it into a small knot and pin it — the headband helps hold everything together.

The most effective trick is to pin the headband to your hair with bobby pins right behind each ear, where the band meets the hair. You can also spray the inside of the headband with a light hairspray to create grip, or choose headbands with a textured or rubberized inner surface. Some people find that slightly teasing the hair where the headband sits creates enough friction to prevent sliding throughout the day.

A messy bun with a headband can absolutely work in a professional setting if you choose a refined headband — thin metallic bands, tortoiseshell, or a solid-colored fabric band are all workplace-appropriate. Keep the bun moderately neat rather than extremely messy, and limit the number of loose tendrils around the face. The headband adds a polished, intentional quality that separates this from a basic messy bun.