5. The Y2K Pigtail Braids

The Y2K Moment: Low, chunky pigtail braids — often worn slightly undone, with flyaways and chunky pulled-out sections — were a staple Y2K hairstyle seen on everyone from Lil’ Kim to Alicia Keys to every teen magazine cover of the era.

The Modern Update: The modern version wears the pigtail braids slightly higher and often incorporates thin ribbon or metallic thread woven through the braid for a luxe, editorial finish.

How to Create It:

Part your long hair down the center. Gather one side into a ponytail at roughly ear height. Divide the ponytail into three sections and braid — keeping it slightly loose and not too tightly secured. Secure with a small elastic at the end. Repeat on the other side. Now, gently tug the sides of each braid outward to loosen and widen them for that chunky, relaxed Y2K look. Pull a few pieces loose at the face and temples.

Pro Tips:

  • Weave a thin satin ribbon or metallic cord through the braid as you go — it looks stunning and reads instantly as Y2K
  • Gel down the baby hairs and edges before braiding for a sleek crown with textured braids — a beautiful contrast
  • Finish the ends with matching ribbon bows for the most authentic early-2000s finish
  • Try starting the braids as Dutch braids (under-crossing) at the top for extra dimension

Best For: Long hair of all textures. Particularly stunning on natural and curly hair.

Modern Occasion: Streetwear looks, music events, editorial shoots, everyday Y2K style.