Fashionable at 40? What should I buy?

[Fortunatepiggy]

So please help me fashionable mums..I am 40 and shop mainly in h and m for casual and m and s / phase eight for work but feel frumpy. I'm a 14 with big boobs and hourglass shape but big thighs and less than flat tummy since ds came along. I tend to wear a shirt jeggings and ballet pumps or maxi dresses on weekends and wrap dresses or suits to work. I really struggle when I have the rare night out because I don't know what to wear. I've got a bit of cash to shop for some new stuff. What should I get to fool everyone into thinking I'm trendier than I am!?