Hairdressers:people who are good with hair- questions about this hairstyle

[OMGitsnotgood]

I have had a chin length bob for a couple of years. It took several years of pain to grow that down from a very short layered cut.
However, I am bored with it and fancy a change. I don't want to go too short or too layered in case I don't like it and want to grow it again. I am fancying something like this photo, but have some reservations:
Would it work with a fringe, which I need/want to have to hide a big scar.
How easy would the curled up ends be to maintain? I fear it would look great leaving the hairdresser then look a mess the rest of the time. How best to do the curls? Straighteners?

All thoughts welcome, thank you

I think it's just a shortish bob with long layers and it's been styled with height at the crown and the flicky out ends. A good hairdresser can get the flicky out ends effect with the correct cut (level of success dependent on youe hair type) but it will always look better styled. This haircut was pretty popular in mid 1990s (e.g. the singer from St. Etienne) and whilst it looks great in the photo I remember seeing a lot of people back then with what I call teenage boy hair (flat, lank) when it's not styled. Obviously products and tools have come a long way since then!

I think the key to the success of this style are cutting it short enough and also a product that gives that nonchalant but thick/voluminous slightly choppy texture.

Thank you @Jeannne92. I think you've voiced my worry that it might just fall flat if I can't style it on my own. I'll discuss with my hairdresser, I like to think she'd be straight with me about whether it would work with my hair & my fairly basic styling capabilities!