Pillbox Hats

• The ever-popular pillbox hat, with various accessories and decorations, is making a comeback when women want to look classically elegant. Victoria Beckham was seen sporting a chic pillbox hat at the Royal Wedding of Prince Charles and Catherine Middleton in 2011. Jacqueline Kennedy wore this elegant style effortlessly in the 1960s. Pillbox hats are characterized by a flat crown and straight, upright sides. Some pillbox hats have veils, while others may sport feathers or flowers. It was originally designed as military headwear by the British during World War I.
  
  

Cloche Hats

• Cloche hats, first popularized in the 1920s, are once again popular accessories.Pixland/Pixland/Getty Images
  
  These low-brimmed, head-skimming hats generally associated with the 1920s are timeless and ever stylish. These hats have evolved from the earlier wider brims to smaller brims. Cloche hats bring an outfit and elegant look together with minimal effort. They generally look good on short hair or hair that is pinned back on the nape of the neck. Cloche hats often cover the ears, negating the need for accessorizing with earrings.
  
  

Cocktail Hats

• These fun, frilly creations, first popular in the 1930s and 1940s, are worn perched slightly forward on the head, often tilted over one eye, and sporting a veil. It is called the cocktail hat because it was originally worn in the evening, but it is now a popular style for weddings and fancy teas. In addition to a veil, they can be trimmed with feathers, flowers, bows and jewels. Their versatility, elegance and femininity have brought them back into fashion.
  
  

Wide-brimmed Dress Hats

• Wide-brimmed dress hats flatter all ages and are appropriate for almost all occasions.Pixland/Pixland/Getty Images
  
  This enduring hat style was immortalized by Audrey Hepburn's character in "Breakfast at Tiffany's." Her Royal Highness The Queen of England is often seen sporting a wide-brimmed dress hat, as she did at the Royal Wedding of Prince Charles and Catherine Middleton. The Kentucky Derby is another event where this types of hats appears in large numbers, decorated in everything from ribbons to flowers to jewels to feathers. The hat is characterized by a flat or slightly rounded top and flat sides that become a wide brim, framing the face and making a very pretty picture of the woman wearing it. Wide-brimmed hats were popular summer accessories in the 1940s, and their popularity never seems to wane.