Pay Attention to Detail

As any panama hat-wearing convent school girl will tell you - what you do to hold on a hat like this is:
brush hair forward;
put on hat with elastic under hair left down at the back;
brush rest of hair from the front over elastic holding on hat that is showing;
secure front of hair to back of hair with pins/laquer/spit/what you will. Otherwise your hat turns into a peculiarly-shaped alice-band, which is what has happened here.
Gloves should never be skimped on. They will not fit and their lumps and bumps will make your hands look like paddles or as if they are clad in baseball mitts. The best thing is not to wear gloves at all if you can't stand the upfront cost and, in the case of gloves, their frequent replacement. They take a lot of use and they cannot be repaired - after all, they are standing in for your hands and should fit like - well - gloves. (Expenditure is reduced if you avoid buying gloves in curious shades of whatever that colour might be. Old duck egg? Particularly nasty bruise?)
Dark shoes in town, particularly with tights or stockings.