The Spring Racing Carnival offers an annual excuse to a) tackle the unfamiliar and uncertain minefield of “a bit dressy” dressing, and b) have an inaugural blow-out. So how does one meet it in the middle? Pleasantly uninhibited, yet fedora-free.

Let us rejoice in the growing movement back towards a more comfortable, languid and leisurely way of suiting – something that saw its extremes in the ’80s and ’90s. The corporate suit, as it’s worn in the business workplace, is waning. And, not surprisingly – that’s what happens when comfort is forsaken for a misunderstanding about what best flatters your figure: suits that are too fitted. To be comfortable is to be yourself, and that rarely involves “skinny” suits or anything that’s tightly tailored.

To see someone who has dressed for ease is both comforting and appealing: looking comfortable is the basis of style. It generates a feeling and an attitude rather than just a look. A lot of tailoring can look aggressive, or cold. [At P Johnson], we believe suiting can be softer and even have a slight edge of femininity to give the suit a natural appearance akin to what we saw with Armani in the early ’90s, when there was a generosity to the clothing that gave it a luxurious sensation. Wear your races suit like pyjamas. It’s very hard to look luxurious when something is very skinny.

As far as suiting goes, soft-tailored lines, pleats, draping materials and clean-but-natural shoulder expressions deliver a handsome, comfortable and elegant “attitude” in a look. The tonality, warmth and richness of human-scale colours including terracotta or denim-blue (as opposed to harsh or hard colours like fire-engine red or cobalt) result in the focus being on someone’s face and personality, not on a cloth-anguished figure with garish distractions. Bold prints can offer sophisticated and playful humour at the races without a sense of affectation, keeping the light-hearted spirit in good taste. This isn’t work –  it’s play. So a silk tie over a linen suit with a linen pocket square adds swagger and charm.

For shoes I like Driving Shoes – they’re a really nice soft-casual shoe. I like the way they dress with a suit and calm it down a bit. Or you could go for a Mountain Boot. I find chocolate brown goes with everything.

If all that’s too scary then consider the virtues of navy and grey mixtures handled minimally. Spend for a future wardrobe here, not just the season. And there’s no need to add perverse adjuncts – crazy socks, misused trimmings, pipings on jackets, unnecessary hats or lapel pins – they don’t make it “a bit dressy”. And finally, a haircut and some elegant sunglasses can ice a plain cake. Have a pleasantly boisterous and comfortable carnival season.

Tom Riley is the Australian director of custom-tailoring and lifestyle brand P Johnson Tailors – which has appointment-only showrooms in Sydney, Melbourne, New York and London – and he knows how to put together a suit better than most. The Principles is a monthly menswear series about timeliness style and nailing fashion essentials.