Hats That Flatter Any Face

  • , by Alex Torres
  • 5 min reading time

Hats are powerful accessories. If you have ever tried one on, you know their trans-formative powers. Large and lovely or diminutive and daring, a hat can work with the shape and angles of your face, creating a striking effect. Even a woman who thinks she is definitely not a “hat person“ may find herself smiling back at her reflection when she puts on the right hat.

However, there's a flip side to hats as well. The wrong hat for your face can highlight or even exaggerate the features you least want to spotlight, accentuating your face in a most unfavorable way. No wonder the ladies avoid women hats!

So here's the key: Looking fabulous in hats is simply a matter of selecting the ones that complement your face. In fact, some hats are so versatile that they flatter virtually any face, practically guaranteeing that you will turn heads every time you step out of the door. Yes, indeed, these are powerful hats.

With all of this in mind, we showcase the five main face shapes, coordinating each with hats that show these faces to their best advantage. What makes each of these hats true standouts is that they also happen to flatter any face equally well.

Round-Shaped Face

Softly contoured, a round face exudes femininity, often giving a woman the benefit of an eternally youthful look. You can savor that girlishness with a fascinator hat, the small, often veiled hats made famous by Princess Kate's penchant for wearing them. Delicately accenting any face, and especially pretty atop a round face, our Jeanne Simmons Sinamay fascinator hats, for instance, are frothy confections of flowers, netting and a sprinkling of feathers, appealing to the woman who truly enjoys being a woman.

Then, for a more tailored look, consider a fedora hat. Traditionally a menswear item, this hat becomes an elegant finishing touch when partnered with flowing skirts or ruffly shirts, adding a chic edge to counterbalance the softness in both the clothing and a round face. Let the applause begin!

Square-Shaped Face

The angular bone structure of a square face often features a strong jawline and prominent cheekbones whose chiseled effect define this face beautifully. Highlight that beauty with a wide-brimmed hat whose dynamic interplay of shadows across your face gives it a glamorous, movie-star quality. Our Jeanne Simmons Toyo straw Bretton hat is the quintessential specimen, with its upturned brim that at once calls attention to the lovely geometry of your face while also softening it.

By contrast, a fitted hat like our Scala LW497 knit wool cloche hat, with a side flower, brings a square face into full and stunning view. Hearkening back to a gracious era when hats were part of every woman's daily attire - along with gloves as well as matching shoes and handbag - this hat's high crown and ridged detailing, along with its small brim, provide an elegant backdrop for a square face.

Heart-Shaped Face

A heart-shaped face graces a woman with an almost doll-like quality. It's the wider forehead, drawing attention to the eyes, coupled with a slender chin, that collectively lend this face its pretty, baby doll look. The bonus is that almost any medium-brim hat will work, enabling you to carry it off with soigné style. Take our Jeanne Simmons poly bucket hat 6454, for example. Its delightful, face-framing brim and airy ribbon-rose trim, enhance that becoming heart-shaped face.

Meanwhile, our Scala LC484 cotton medium-brim bucket hat is a pop of vibrant color in your wardrobe, a playful touch that lights up even your old standbys. It's the brim that makes all the difference. Sweetly accenting a heart-shaped face, the turned brim along with the array of hues bring out all your inner charm.

Long-Shaped Face

Long on beauty and not mere length, this face has the exquisite look of refinement. Adding to that polished countenance is the perfect hat. What better way to enhance a long face than with a beret? An unconstructed hat that is attractive on every shape of face, our beret 50 by Scala is particularly well paired with a long face. Worn on an angle, this hint of French style accentuates the leanness of your face, while minimizing its length.

Similarly, a wide-brimmed hat is a nod to the posh look of a long face. Our Jeanne Simmons nylon wide-brim hat offers Downton-Abbey style graciousness with its floral embellishments and soft brim, delicately surrounding your face. Meanwhile, our Jeanne Simmons ribbon wide-brim hat, with its bold stitching encircling the crown and brim, offers an aura of distinction. Both visually widen your face while their brims flutter around it daintily. Sometimes, being a woman is pure fun!

Oval-Shaped Face

Perfectly proportioned and almost flawlessly symmetrical, an oval face is the easiest for wearing hats. Of course, if this is your face shape, you probably already know how sensational you look in any hat you select. From the smallest chapeaus mentioned here, the fascinators, to the grandest in size and style, the wide-brimmed hats, oval faces have the decided advantage of looking beautiful in all hats. Why settle for a baseball cap, when you could have a hat collection with an assortment of transformative styles?

The right hat demonstrates the innate beauty of your face. Since there is no such thing as a bad facial shape, make the most of yours, wearing hats that flaunt your facial beauty.


New to these Hats? Read our Guide to Get you Started

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