I think the first one with the bold accessories like you said is the best choice for pref, because it will be the easiest to dress up. Also, it's cute.
Target is a really good place to find cute shoes and accessories in one stop...that's where I usually go for both shoes and jewelry these days.
If you pick heels bring some flip flops to walk in between houses.
Re: weight...make sure you're being healthy while losing weight...recruitment is
NOT worth making yourself sick or developing unhealthy habits. (And I don't mean to assume that you're doing anything extreme, just throwing it out there.)