I don't think she dresses badly for any old girl on the street.
She doesn't dress up to code (IMO) for someone who is dating or even seriously considering marrying into the British Royal Family.
Look at the recent women who have married into the BRF in the last forty years (Diana, Sophie, Sarah, Camilla, Autumn and now Kate). I realize that the dress sense has changed (and both Diana, Sophie and Sarah in their early days had some not so nice outfits but it was the 80's/90's). Autumn isn't close to the throne due to lack of title, and the number where Peter falls in BUT she dressed apprpriately when out in public and when meeting the Queen. Chelsy dresses like a WAG. Even her appearance at Peter's wedding looked WAGish to me. I am not saying she shouldn't be herself but she needs to temper herself down a bit.
Now that isn't to say that she isn't a nice girl, or smart. Cause we haven't heard that wasn't either of those things.
I think Harry and Chelsy need to sit or get off the pot. If it isn't going to go any further than this ( neither of them want marriage that is totally different), they can date or whatever. But the facts remain the same...Chelsy has indicated that she doesn't want to live in the UK, Harry hasn't indicated that he is willing to give up being 2nd in line to the throne. Either one of them needs to give up their dreams (or life) or move on.