The square face shape is best complemented by hats with rounded edges, which help soften strong angles – especially along the defined jawline. For shorter face lengths, opt for taller crowns and narrower brims to create the illusion of added height. Asymmetrical styles also work wonderfully, offering contrast and softening the overall look. Top hat choices for square faces include the floppy fedora, upturned brims, peaked beanies, berets, and the timeless bowler. Penelope Cruz is a great example of the Square Face Shape…
If you have an oval face shape, consider yourself lucky – this versatile shape suits almost any hat style with ease. Most styles will flatter just keep in mind that the crown should not be narrower than your cheekbones, and it’s best to avoid snug beanies with oversized pom poms, which can throw off balance & elongate unnecessarily. Asymmetrical styles worn across the forehead can be especially flattering, adding interest while maintaining harmony. Cindy Crawford is a great example of the Oval Shape Face…
For heart-shaped faces, hats with a medium-sized brim work best to create visual balance with the wider forehead and narrower chin. Avoid overly wide brims, as they can exaggerate the narrowness of the chin, and steer clear of very small brims, which may draw too much attention to the upper face. Instead, opt for styles with soft curves or asymmetrical designs that can be worn at an angle to help soften angular lines. High crowns aren’t necessary, as heart-shaped faces generally have enough vertical length.
Great hat choices include the cloche, bucket hat, medium-brim fedora, and the elegant pillbox – all of which flatter and enhance the natural proportions of this face shape. Reece Witherspoon is a great example of the Heart Shape Face…
 
See this fabulous website for a description of all the hat choices.
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