Matching your hat to your shoe to your bag, or your necklace to your earrings, has a tendency to look dated. Mixing up your accessories adds interest to an outfit, and can make you look much more modern and polished.
Only buy things that make your heart sing. If I don't love it, I won't buy it.
Don't let fear or insecurity stop you from trying new things. Believe in yourself. Do what you love. And most importantly, be kind to others, even if you don't like them.
If you deny the reality of your body or your life, you'll never be able to dress any of it well - even the parts you love. You have to see it all to work with any of it.