I always wear ankle boots in the winter, and sometimes high tops in the summer, and usually with dresses. Bare legs in summer, with midi length dresses, and black tights or leggings in winter, with shorter dresses in cord and wool. I wear trousers and jeans too, but either roll them up or wear ankle grazers. I don’t own a skirt at all, but I do have several jumpsuits. Ankle boots go with everything, and they are so comfortable. They are great with leggings, because you can’t see the end, and great with tights, because you can’t see any wrinkles. I tend to buy flat ones because I find walking in heels difficult. I bought a beautiful pair last winter, lace up, a bit like Doc Martins, and with embroidery up the side of the ankle. They are flat, waterproof, leather, with a good grip on the sole, and I can walk miles in them.