How to know if you can get away with wearing that hat

One of the most recognisable, yet hardly very fashionable, accessories doing the rounds at the moment would have the be Donald Trump's Make America Great Again red cap, made famous for all the wrong reasons.

At school, most of us were probably forced to wear a hat on the playground (no hat, no play as the saying goes) which meant for most of us, this was a wide brimmed, cotton hat with breathing holes and a string to keep it from blowing off our heads or leaving it behind.

Depending on where you went to school, you may have been lucky enough to wear a completely non-versatile straw version, or if you were like me, it was a baseball hat for high school with an embroidered school crest (style points with a matching blazer and your standard school shoe). 

So this begs the question, can you get away with a baseball cap if you're over 50? A bucket hat if I'm in my 30s (wait, scrap the bucket hat all together), or an Akubra hat at a festival with the wind blowing?

Let me break it down in this simple guide.

In your 20s

During this great ten years of your life you can probably experiment the most with fashion styles, but that doesn't mean there's an excuse an unfashionable or ill-fitting hat. For example, if you opt for a baseball cap, keep it simple. Black, or navy. Limited embroidery, absolutely no animal prints and categorically no fluro.

Tips: If you're going to wear a sports team baseball cap, ensure you know the difference between the Dodgers and the Yankees, and the code of sport you're supporting with it. In terms of care, limit the amount of sweat you produce wearing one. There's nothing more unsightly than visible sweat marks on a hat while you're eating your brunch.

Our pick: This great printed cotton-canvas cap from OFF-WHITE is the perfect millennial cap. Wear round the front, or backwards for a cool, New York street kinda vibe.

In your 30s

When it comes to this decade, there's a good chance you will mix between a decade past and a decade ahead.


One style of hat that seems to live in a safe space in this decade is an Akubra. Think less Mariachi band and more Pharrell Williams, this hat should be a statement piece which complements your entire outfit. Don't be a afraid to mix it up with light browns and sandy coloured hats, or even light grey.

Tips: Consider where you're wearing your hat before you wear it. Sure, it's a style piece, but no one wants to sit behind the Drover with his hat on whilst at the cinema (indoor, or outdoor). Clean it, and steam it. Keep your hat lint and crease free – it's a simple as that.

Our pick: The Bogart by Akubra is the classic fedora style, in black. You can't go wrong.

In your 40s

Here you need to keep it cool, and we mean literally. Afford yourself a classic Panama hat for the summer. An investment it is (between $800 and $1200 from Sydney's Strand Hatters), this type of head gear will set you apart from everyone else, and is actually a versatile summer wardrobe option.

Tips: Make sure you take the time to get the fit right – a Panama needs to fit perfectly. Oh, and please care for it properly. Get a hat box or wear it whilst travelling to avoid rolling into your carry on at all costs.

Our pick: This Kaminski Panama hat with blue grosgrain ribbon detail makes it the perfect addition to any summer wardrobe.

In your 50s

There probably aren't really any rules when it comes to this decade – you probably want comfort, and to protect what hair might be receding so really the choice is all yours. Something practical works well here, and again, like the 30s – you can really make each of the decades work for you in the best way possible.

This decade is really the opportunity to work more of a holiday mode (you deserve it) and opt for a nicely woven straw hat.

Chose tan or white in colour, and keep it simple. If golf is more your thing, add a flat cap for classic style that you can wear on and off the course.

Tips: Don't buy something you aren't comfortable with. Keep the colour selection tight. 

Our pick: The Lock & Co brand is almost as old as time itself and this wool and this Alpaca blend style not only looks good, but has internal ear flaps that can be folded down when its too cold not to.