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would this hair look stupid?

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If your hair is curly there is no point in looking at photos of straight haircuts because it will never look like that (unless you want to straighten it every day and avoid rain like the plague).
You're better off looking at the photos of curly hair that people have posted to see what will look good.

Ive had a bob all my life though, so am looking for something different. I did try an asymetrical style once, very short on one side with the other side chin length and it actually managed to stay straight. It looked ok wavy too but some days it looked boyish other days it looked feminine so I grew it. Apart from that my hair has always been in a bob lol. Im not really into long feminine plain styles though I like something a bit different/funky but as you said I need to work with curls rather than against. To me curly hairstyles all look too feminine and the same though.