When is it time to let your hairstyle go?

[sweggeh]

What used to look cool when you was young and had a head full of hair...

http://cdn.ticketfly.com/i/00/01/10/00/21-exl.jpg

Arent necessarily going to look good now...

http://i.ytimg.com/vi/UUzd2x0BSyo/maxresdefault.jpg

Yikes

[Vaniiiia]

He's a 15 pointer!

http://bloximages.newyork1.vip.townnews.com/stltoday.com/content/tncms/assets/v3/editorial/4/6b/46b1278f-d7b1-5289-97fa-61b35138fd1d/541a1c5105f14.preview-620.jpg

[Knicks101]

Would anybody even know who he was if he didn't have the hair?

[KnittingRyu]

To answer the OP title more directly: The moment you ask yourself that question, it is time for a new cut.