How To Pick the Right Hat

During a recent Facebook conversation, I had a request from Bethan – a lovely long-time client of mine, residing in Canada. She wrote “I currently have a choice between a baseball cap (which I think is great when I actually go to the baseball, otherwise not so much) and a wide-brim floppy hat that just doesn’t flop ‘right’. How do you look stylish while protecting from the sun?”  And it seems Nicole from Brisbane concurs… “I love Bethan’s idea, how can we be sun-smart & look good?”

I don’t wear many hats myself, except at the beach. I have a fear of hat-hair and a preference for sunscreen & mineral makeup is my personal solution. But with so many styles to choose from, it can be difficult for us to know what to wear, where and when. So here I’ve put together some of the more popular or wearable styles and my suggestions of how to wear them. I’ve also added some pics for further inspiration…

The Cloche

Also pictured above on the gorgeous Hilary Swank in P.S I Love You, the Cloche is one of my favourites. And it would seem Gerard Butler is quite partial to them too! It’s a stylish, classic, vintage style which looks exceptionally lovely in winter (usually made of felt or boiled wool). Wear it with a trench coat and boots, or a knitted shift dress, opaques and flats.   The Cloche can also be worn in summer, (often called a bucket hat and less structured) but be sure to go for a lighter fabrics, even crocheted or straw.

The Wide-brimmed Floppy (aka “Sun Hat”!)

The key to nailing this look is all about “the fall” of the brim.  If the brim is too stiff and structured, it changes everything. The only way to get this right is to try on as many as you can before you buy. Remember though, hats will soften and mould to your head over time, so even if it’s a little bit stiff to begin with, all is not lost. My tip is to go for the most neutral shade you can (as pictured here) and to add your own touch of colour via a ribbon or trim around the crown. Best worn in Summer with lightweight fabrics and pretty summer frocks.


The Trilby & The Fedora

The Trilby is just a type of Fedora. The key difference between the two lies in the brim. The Fedora is usually wider-brimmed. The Trilby generally is upturned at the back, and has a shorter brim. These are both the embodiment of cool and sophistication – somewhat masculine in their styling. This is one type of hat that I really think has to match the personality. I would argue that it almost takes a little more confidence to wear this type of hat, but I really can’t put my finger on why! Perhaps it’s because I think of them on suave, sophisticated Hollywood-style actors of yesteryear, and we also don’t generally see them on shy, retiring types?   The Trilby (pictured above on Jessica Alba – photo credit Splash News) looks great, but really does very little in terms of sun-protection. The Fedora (pictured above on Harrison Ford aka “Indian Jones”) does a lot more in terms of sun-smartness and is generally a little more casual too. The choice is yours really!


The Baseball Cap

A classic. A favourite. A universally stylish hat to wear when walking, exercising, at the park, at the Baseball (daah!), at any sporting event really. Casual yet simple and classy, I usually like to go for something simple – in a colour that complements the outfit (of course!). I love the simplicity of a plain Polo Ralph Lauren version for everyday outdoor activities, and for specifically sporty pursuits, a more sporty logo’d style is great too. Really there are no rules – where whatever you like to any of these pursuits…as long as you feel good!

The Trucker’s Cap

Hmm…I gotta say, this would have to be my least favourite. The very history of the cap itself plays a big part in why the cap is often considered “bogan”.  To quote Wikipedia’s definition, “It is also sometimes known as a “gimme [as in ‘give me’] cap” or a “feed cap” because this style of hat originated as a promotional give-away from feed or farming supply companies to farmers, truck drivers, or other rural workers. Trucker-style hats can now be found with other pictures, logos, flags, camouflage, or humorous sayings on the front. Trucker hats are still available as promotional items.”  The main difference between this and a baseball cap is the high crown. The baseball cap hugs the forehead in a natural curve, whereas the trucker’s cap tends to sit high on the crown, made of foam at the front and generally mesh at the back.  The choice is yours…both styles will keep the sun off – it’s just a case of which style you like best, I guess!?



The Cowboy Hat

Think Molly Meldrum. The Akubra. Man From Snowy River. Love ’em or hate ’em, the iconic Cowboy hat has been (and will be) around forever. If you live on the land, live in your RM Williams, then clearly this style has “you” written all over it.  But what if you live in the city? Can you wear one and not look silly? Yes, of course! But only if this is a style that suits you and your personality that is! Try a straw version with a floral sundress in summer. Or jeans and a tank for a truly casual country feel. Whichever you choose, carry it off with confidence and style – and girls, preferably wear your hair long, loose and natural to really wear it well.

In summary…

This is by no means a full glossary of all the hats available. I haven’t even mentioned the pillbox, the top hat, the beanie, the beret, the flat cap, the bowler, the fez, the Panama,  the hard-hat, the Stetson, the turban and countless others!  There really is no right or wrong. You just choose whatever style suits the occasion, your personality, lifestyle and the climate. Much like most considerations when it comes to style really! You have to kiss a few frogs before you find your handsome prince. And choosing the right hat is much the same! I hope this has helped you decide which is right for you…or at least “what to wear where, when and how”!

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