Winter is easy. Throw on a coat and a jacket and at least you can layer and lie your way to a look. Come summer, the artifice has to go.

But how do you keep cool without dressing like an overgrown teenager?

Short Sleeve it.
Let’s start with an easy one: the short sleeve shirt. I’ve never been a fan and have often suggested you skip it altogether in the past, but recently I have been giving it a rethink.

The truth of the matter is, short sleeve shirts that look like you’ve just finished your shift at the Queensland Department of Parks and Recreation circa 1974 and simply have no place on the street. They’re dowdy, degrading and instantly suggest, ‘I don’t know about much’. Add a sweater vest and you’re running for Republican Governor. If that doesn’t shake your desire, then God (will) be with you.

What then? Wear a short sleeve shirt with gusto. Fine and small pattern repeats give the look embellishment and personal touch. Make sure the sleeve (and body) is slim and a little short, you could even roll it up a hem or two; make it about the length of the sleeve of a T-shirt. Give it some attitude by wearing raw denim or some faded out, loved jeans. Think ‘50s American workwear or English mod. It can be done.

Try a hat.
Fashion is about looking like you know what you’re doing. Good fashion is making it appear like you don’t care how. This is where confidence is key. Throwing a hat into the mix can make or break you. You can look savvy and nonchalant at the same time by: 1) avoiding a fit like a pillbox, even jumping a centimetre in size to get a cool dropped-down look, and: 2) getting a light-coloured straw or panama with a medium brim for casual sophistication. Too small will evoke Tommy Lee levels of douche-baggery and too big and the hat’s wearing you.

Check out Smart Alec in Melbourne for a great summer selection and great help. Henry Bucks and Strand Hatters know their chapeau business like the back of their hand too.

Slim soles
Ditch the heavy soles for summer, but don’t stop wearing shoes. And by shoes I mean grown-up, now-you’re-a-big-boy shoes. You want the day to continue into night? Then wear the right shoes.

Go for a slimmer sole, a gentle lace-up or even a loafer (which work well with shorts) and subvert the conservative lean with colour and consideration. Leather’s not your only option; canvas has an F. Scott Fitzgerald ‘old sport’ appropriateness about it too. The colour doesn’t have to blow minds – maybe navy with a white or clay sole, or a natural linen colour with off-white laces. Lose the socks too and imagine the Mediterranean breeze hitting the shore and your ankles.

Church's, Loake, McNairy and Common Projects will have you stepping in the right direction. Beggar Man Thief is a great, knowledgeable stop for any shoe requirements. Also consider 124 Shoes on Russell Place for lightweight, well put-together shoes you won’t see anywhere else and Harrold’s for beautiful high-end examples.

Strike the balance.
Wear long sleeve shirts with shorts. This, for me, really isn’t an option – it’s a rule. The shirt need not be slim (though not tent-like), but avoid anything remotely business-like in weight, texture or look. So instead of sturdy poplin, a soft, visible weave with equally soft collar is your goal. Roll up the sleeve, un-tuck and let summer come to you.

Shorts for occasions (almost an oxymoron) should be trouser-like in finish and know that shorter is better than longer. If they have to be tailored, then do so. Look for established brands, such as Country Road or APC. Slowear is an amazing Italian brand famous for their approach to clothing, treating it the same way the slow food movement does good grub.

Fashion shorts are very, very dangerous and should be treated with caution. When it comes to the beach, if you want to rise above the fray, look to Orlebar Brown, sophisticated trunks suitable for both swimming and peacocking, most recently seen on the backside of Daniel Craig in the latest Bond.

Hot legs.
Except for the hottest of days, denim is great, but avoid looking out of place and get some grey jeans to replace your blacks and indigos. Make them light too. Stewing in a prison of denim is all too common, uncomfortable and avoidable.

The answer you’re looking for is chinos. Like the sweater vest, chinos in the wrong hands are a crime against rational thought and reason. Fight back with chino-weight cloth, but made in reputation-saving jean-style cut. APC do this extraordinarily well, and you can find them at Incu. Alternatives include Noir’s grey and khaki jeans in a great cut at Up There Store.

Linen is bold, too bold in fact, and Australia has neither the history nor the wherewithal to pull it off. We simply don’t understand it like the Europeans or South Americans do. The creases are the charm if you want to know.

So instead, stick to cotton. Yes, it will crease too, but that will keep the fear of looking too neat at bay. Don a blazer or suit with seasonal aplomb; for work or after work, a crisp white shirt under a steel coloured suit is the business, but lose the tie in summer (as soon as you can) and wear with a couple of buttons undone. Patrick Johnson will sort out a made to measure suit in weather appropriate cloth and even take care of complimenting shirts in comfortable weights to complete the wardrobe.

You should have it covered now. Keep it light, fresh and flexible. If you’re thinking you look too casual, you probably are. Shorts are for hot days, not every day, and shoes maketh the man.