Your shoes or boots haven't seen any polish since they were bought. You probably only wear two pairs of the many you have hidden in your wardrobe. Throw out every single tired-looking pair. Once you have banished the trainers and the scuffed chunky heels, you'll see that your legs and ankles do have a good shape and benefit from a lighter style of shoe (that isn't black, either).
You need to throw out all your make-up. We know you haven't bought anything new for years, and cosmetics do have a sell-by date. The colours you have are probably all wrong for you anyway. Remember the key basics: if you have a very lined skin, avoid powder and go for a moisturising foundation instead. If your lips are thin: opt for a lip gloss rather than a lipstick.
You will probably always want to carry your life around with you, so don't go for small. Find something that will hold the kitchen sink, just do it with a bit more style. Choose a bright clashing colour like orange - it will really give you a kick.