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The Everygirl’s Guide to Must Have Hats

The Everygirl’s Guide to Must Have Hats

Y'all, I'm so relieved that First Lady Melania Trump and Meghan Markle (a.k.a. Duchess of Sussex) received my memo about hats being the new "it" accessory!  (Ok maybe I exaggerate...)

But I am glad to see these high-profile fashionistas embrace the topper trend, because the right hat is like the duck tape of style:  it holds everything together, serves a multitude of useful purposes and won't break the bank!

Hat Tricks

A good hat frames your face, shields you from the sun, adds a touch of panache to your outfit, and BEST OF ALL - it saves you the time and fuss of trying to make something decent of your hair.  For girls like me (all thumbs on both left hands) this last one's a game-changer.  I'm all about the ponytail-and-forget-it approach to hairstyling. A hat takes my laziness and makes it look polished, and dare I say, even stylish!  I'm sold.  So, yes, I'm hat-obsessed this season, and I think you should be, too!  Here are a few of my favs, tips and tricks!

What is your face shape? 

Of course, you can wear any ole hat you like.  But, just like the cut of a pair of jeans and the drape of a dress...what you put on top of your head will accentuate (or downplay) what's underneath.  


 If you're of the cherubic round-faced variety,  (full cheeks, face about as wide as it is long), try a hat that's got a taller crown.  It will slenderize those adorable cheeks and give a touch of sophistication.

  • Cloches are clever, & fedoras are your friend. Two great ways to style your fedora: with skinny jeans and a tunic, or a flirty dress. Here's a great fedora for under $30 from Target!

  • To balance out the roundness, try wearing your hat at an angle, so the brim doesn't cut a horizontal line across your forehead and accentuate the width of your face.


If your face is long, and pretty straight from your forehead to your jaw, go for:

  • a wider brim

  • a hat that sits lower on your forehead, to soften the length of your face.

Try a hat with a deep crown that cuts across your forehead and balances the length of your face. Or, go for a beanie or beret with a slouchy fit - the curves will balance your angles. Another great choice: a ballcap that rides lower over your forehead.  Ballcaps look great with casual dresses and jeans.  And beanies look super cute with bulky sweaters - Amazon has a cute selection here.


If you have a wide forehead and cheekbones and a strong jawline, you can soften things up a bit with hats that have rounded crowns; floppy hats work well for you.

The goal is to create softness that counter-balances your strong facial structure.  Fedoras might be tough for you to pull off because of their strong, angular lines, but a Panama or hat with some curve to the brim may be perfect!  Here's a cute plaid one from Anthropologie.


If you have a wide forehead that tapers to a pointy chin, avoid wide, round brims, which will accentuate your forehead.  Instead, head over to the fedora department. 

  • A tapered fedora or trilby (basically a fedora with a narrower brim) will balance the upper and lower parts of your face. Here’s a women’s trilby in classic black that will take you through Fall and winter in style!

The above are guidelines, of course.  Honestly, just try out some different looks!  Here are my go-to's:


My hubby says his all-time fave look for me is when I'm wearing a ballcap...sort of that all-American girl thing. (I'd really hoped he'd choose diamond tiara but alas, that option didn't even get a mention...)  In any case, I love to wear ball caps in interesting fabrics; it just takes the casualness of this style up a notch.  I have a burnout velvet, a pink tweed and a neutral green velvet ball cap, all purchased on sale from Anthropologie, and I throw these on when the OOTD is street-chic (e.g. I didn't wash my hair that morning.) Looks great, and the frizzy mess underneath is my little secret - Shh!

Another fav is the classic cowboy (cowgirl?) hat.  Looks equally great with sundresses and swimsuits.  Throw on a pair of hoop earrings and aviator sunnies and you're done. 

The floppy hat:

If you’re headed someplace warm and beachy, you need this style.  It practically comes with a mimosa and sunscreen built-in!  And, I personally love the current trend of adorning oversized floppy hats with pompoms, ribbon or scripted sayings - the whole point of this style is to accessorize you vacay!  You can get extra-creative and customize your own with this Etsy shop (cool gift idea, too!) 

The Grand Finale

My last and best hat style is the LBD of all hats (drumroll...)  The Panama Hat.  This style looks great on every face shape and can take your jeans, maxidress or shorts and sandals to the next level, fashionably speaking. There are loads of different versions of the panama hat, but most are made of straw (or a synthetic variant on the texture) and many are packable for travelers. 

Voilá! I hope you find a style or two (or more!) to have fun with this season. They’ll add interest and intention to your outfit — meanwhile, “hats off” to you, for being fabulous!

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