Go to a decent hairdresser & ask them, if they are any good they will be able to tell you what will & won't suit you. Also ask your friend's opinions.

I generally think short hair on women carrying any excess weight can make them look at bit bottom-heavy, as in everything seems to be happen below the neck! A fuller hairstyle can help to balance things out. I think short hair can look great on women/girls with small, pixie-type faces and delicate bone structure, but you do need a really good cut.

I agree about asking a pro but, in general, I think if you can pull off a ponytail with little to no hair in your face, you can pull off a short haircut.

find out what your face shape is...if you have an oval or round shaped face you can work almost any style

Do a search online for a site where you can upload your photo and "try on" different haircuts. Once you find one that you think suits you, just hit print and bring with you to your stylist. I found loads of free sites like this and I love my new 'do!