Well its Spring so its a good time for this. A lot of the on line retailers like John Lewis and M & S have a styling page where you put in all your details and it makes recommendations for the kind of shapes etc that may suit you. I have just done the JL that was very helpful. Also you can book a session with a personal stylist in one of the stores with no charge and no obligation. You could ask a friend whose style you admire to go o a shopping trip with you. If it were me I would start with the hair and make up makeover first - go to a good salon and then buy clothes to suit your new you.
As to clothes the stylists say throw out (donate) everything in your wardrobe you haven't warn in the last two years to make some space then start again with some good basics and build up a flexible capsule wardrobe.
I'll come with you and be your stylist if you buy coffee and cake. [Good luck with it sounds like a fun. 
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