image001image002Gone are the days of the elegant hat for everyday wear: the rosette-covered cloche, the feathered chapeau, the ribboned bonnet, the “fascinator.” (Look it up)  Unless you’re dressing for the Ascot races, you’ve no doubt noticed that the minimalist direction of fashion has invaded the millinery world. But this doesn’t mean that a hat can’t be part of a fashionable look. So how does one determine the best hat to wear?

Much of the same things we look for in clothing also determine the most flattering style of hat on us:  personal style, height, bone structure. These things are often more important than simply face shape.

image003Generally, hats are pretty costume-y. That means that anyone who is intrinsically dramatic or high spirited or who feels comfortable in a “costume-y” look can get away with a lot more varieties of hats than someone who is more Classic and wouldn’t be caught dead in a costume. And then there are the Romantics, who usually like to show off their hair unless they’re wearing something to seductively cover their face.

Speaking of which, hair is often the reason we reject any number of styles that might work for us. This is particularly true for those of us with curly hair (and the reason I rarely wear them.) The reality is that most hats look best on straighter hair or curly/wavy hair that is partially pulled back away from the face.

image004Size matters. You don’t want to put a large, floppy, wide-brimmed hat on a small person.  All you will see is the hat. Conversely, the taller you are, the more you can get away with a wider brim.

image005There aren’t a lot of don’ts for who can wear what hat. It all has to do with proper proportion. Broad face, broad brim; smaller face, closer fitted brim and crown. And then face shape is an important element. For example, a round face can carry off a closer fit round shape like the cloche style here. The only exception is for someone with a very long, oval-shaped face. They would look more balanced with a hat that has something of a brim and a fitted crown than with a beret or a beanie. 

image006But most head/face shapes can wear some form of beret. The point is to pick one that creates balance with your bone structure and that works with your hair volume. Big volume, bigger beret cap. Smaller volume, closer fitted cap. A Newsboy cap works for a wider or square-ish head like  Drew Barrymore’s here. image007

image008The Fedora, or Panama hat (they’re pretty much the same shape, though often of different materials) has seen a revival in the past few years and can be very chic for many women. image009The sharp brim of Reece Witherspoon’s short-brimmed Panama here gives a nice counterpoint to her pointed chin and her heart-shaped face. Jennifer Aniston’s would work too, but the brim is competing with the top of her glasses.image010

Cowboy hats usually require a broader head. The turned up sides would just elongate a face that is already long. Anne Hathaway’s rock festival-like floppy straw version with smaller brim is a good compromise for someone who wants the style but not the exaggerated silhouette. And speaking of straw – just about anyone can wear straw and many styles are available in straw.


image012And almost everyone has at least one baseball cap in their closet. (Well, maybe not the Queen…) Pay attention to the shape and the width of the brim. A curved brim is more flattering on almost any face than a flat one, particularly for someone with a longer or narrow face. If you have any kind of a poufy hairdo your hair may stick out from the sides of the cap, making you look a little bozo-like. Your hat should be a thoughtful accessory that adds to your cache, your mystique…and not the image that goes viral on your teenager’s Instagram feed.


[If you want to learn more about your personal style, Andrea’s book Shopping for the Real You is now 40% off from now through Dec 10 on her website. Enter coupon code: 40now.]

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