How to wear cloche hats: Cloche hats are ideal to wear to holiday parties and weddings, as well as at cocktail parties and unofficial meetings. Match it with ladylike dresses, skirt suits, coats and trench coats. A pair of leather gloves and court shoes or classic high boots will complete your super-stylish look. Great advice! Now I just need to find a cloche hat that will actually fit around my enormous gourd, LOL.