08 Oct 2018


Written by Luc Wiesman, originally published on dmarge.com 

For some, spring racing is Christmas come early – a chance to get the guys together, suit up, and knock off some lukewarm beer in plastic cups on company dime. It’s the only time of the year where you can get completely rinsed in a marquee tent and look like someone your grandmother might respect in the process.

Year round, most of us are restricted to the simple sartorial palate of corporate life. During racing season, not so much. Between Stakes Day, Caulfield Cup, and the venerable Derby Day, there’s opportunity to wear the stuff that’s been burning a hole in your wardrobe since you bought it after Friday drinks three months ago and never got the chance to wear it.

With that in mind, we’ve partnered with Calibre to bring you enough sartorial inspiration to see you through Spring Racing with your sense of style (if not your wallet) intact.

The Fundamentals

Acing the racing season is about more than just getting your boss to cover the expenses on the day and ensuring you don’t fall face-first into the grass before you’ve won your money back.

Your Suit Choice Is Everything

Men's Slim Mid Blue Suit   Men's Raceday Suits

If there was only one non-negotiable for racing season, it’s finding the right suit. The classics – navy and grey – are reliable options and if you’re hitting multiple days on the track, you should set one aside for a classic two-piece. That being said, the more casual end of the spectrum – Caulfield and Stakes – is more forgiving on tonal variants like khaki, beige, and cream.

As with your work suits, synthetic materials are for suckers. The races aren’t for throwback master-fit tailoring, but that’s not to say your suit should be tailored to resemble compression wear. Keep it slim (not snug) and you’ll look your best.

Shop Suits

Wearing What’s Known As ‘Separates’

We (more or less) lied, it’s no longer expressly mandatory to suit up at the races. Separates can be worn on Stakes Day and some braver gents will give it a crack at Melbourne Cup. Use a dedicated blazer for the occasion (and not one of your suit jackets). Cotton and linen are great alternatives to wool, and with less focus on tradition you can experiment with different colours – beige, salmon – if navy and grey isn’t your cuppa.  

A Perfect Shirt Is Everything

Gone are the days where a crisp white shirt was mandatory for entry to the races. With the exception of Derby Day (which we’ll get to later) you’ve got way more to choose from. If it’s a white shirt, go for a cutaway or spread collar and a bit of texture to differentiate it from your work stuff. Patterns – florals, checks, and geometry – used to cop a bit of heat but can (and should) be done. Make sure it’s tastefully coordinated with your tie, and don’t go for a pattern salad.

Shop Shirts

Shop Men's Shirts for Spring Racing Carnival  Shop Men's Shirts  Shop the Raceday Look

Choose Your Footwear Wisely

Even if you end up losing them on the night, you’ll never make a good entrance to the races without solid footwear. Here we break down the classics and the upstarts that might be better options.


Calibre Dress Shoes

And their close relative the Derby shoe, will be your bread and butter for the season. They should be leather, not purchased from the bottom of a clearance bin, and polished before the day.

Shop Oxfords


Shop Men's Calibre Loafers

On the other hand, are the next best thing (and twice as comfortable). Suede, horsebit loafers or even driving shoes add a rakish, dressed-down element to the pomp of the day.

Shop Loafers

Only The Best Accessories

Everyone seems to enjoy a good accessory binge during racing season. And while we acknowledge there might be a peacock hiding inside every solemn corporate gent, there are rules about when and when not to deck yourself out in every piece of shiny treasure under the sun.

The Perfect Tie

Knitted or grenadine – are a must (you’re not going to Friday knock-offs after all). Keep the colours simple and make sure you don’t overload the look with patterns. Avoid anything Wall Street shiny or wide, and don’t layer a patterned tie over a patterned shirt – thick plain tie, patterned shirt, or vice versa.

Shop Ties

Expert Tie Tip

Tie knots are the next key thing: unless you fancy resembling our recently-knifed ex-PM, stay away from the ugly and pomous Windsor knot and think about a more rakish alternative, like the double four-in-hand (sorry, Malc).

Shoe Men's Ties

Lapel Pins

These are a staple, but can be tricky: too much colour coordination looks like you hired a personal stylist (no good) but if if you’re not going bling-heavy elsewhere, just make sure it compliments your outfit’s primary colour.

Tie Bars

Another popular accessory but again, the wrong one will scream ‘corporate’ in an environment where everyone is trying to forget about Microsoft Excel for a day. A slim silver bar with mild detailing is all you should need.

Pocket Hankies

Shop Calibre Pocket Squares

Following ties,the pocket square  is a mandatory feature on your outfit. And the only real rule is to never, ever match the hankie to your tie, unless ‘budget wedding package’ is the theme of the day (which it never is). Otherwise, go your hardest with colours, patterns, and so on.

Shop Men's Race Day Accessories


Every man should own a good pair of cufflinks. Make sure they match the colour of the rest of your jewellery (i.e. don’t mix gold with silver) and there’s nothing wrong with a subtle novelty piece – plain cufflinks have been done ad nauseam before.


Another area where you can add some colour – but avoid the pull of being the ‘funny socks guy’. Alternatively, feel free to bin standard socks entirely and wear invisible socks. #FreetheMankle


This is governed by the style norms you’d see anywhere else: when in doubt, less is more. Resist the urge to deck yourself out in six wristbands and a ring-per-finger like an extra in a pirate movie.

Caulfield Cup

At Caulfield Cup on October 20, aim to look smart, not slick. A jacket and tie is still mandatory, but there’s no pressing requirement to wear a matching suit. Chinos and a jacket are acceptable (but you’d be pushing it with jeans). Every other bloke will be wearing a navy blazer and white shirt, so don’t be afraid to change things up with a floral shirt and plain tie combo. Caulfield is a more relaxed affair, so dress accordingly.

Shop Caulfield Cup Looks  Shop Caulfield Cup Looks

Derby Day

Racing season overall has moved with the times, but Derby Day hasn’t quite (yet). Derby Day is all about convention, and it’s a day of sartorial sobriety that’ll always be anchored in subdued, classic style; which means black, white, and (maybe) a little bit of grey. But that’s no reason to say you have to look like you’re heading to a wake: a contrasting double-breasted waistcoat can do wonders to lift a black suit out of funeral territory and patterns, if they fit into the colour triad, are another solid pathway out of dull-and-staid.

View all Derby Day Looks

Shop Calibre Derby Day Look   Shop Calibre Derby Day Looks

Melbourne Cup

Melbourne Cup is still governed by the requirements of a suit, tie, and leather shoes, but in 2018 you have a bit more scope to bend (but not break) the rules. It’s spring, so incorporate lighter tonal variants of navy, beige, and charcoal, and use soft texturing to dress your look down. The sockless suit trend has gained a bit of momentum in recent years, as have knitted ties, loafers, and other more casual pieces to replace the classics.

View All Melbourne Cup Looks

Shop Calibre Melbourne Cup Look   Shop Melbourne Cup Look by Calibre

Oaks Day

Shop Oaks Day Look by Calibre  Shop Men's Oaks Day Look

Known as Ladies Day, Oaks Day is a fun, not-too-serious event traditionally associated with pastels, spring themes, and silly hats. It’s a solid opportunity to unleash your prized statement piece(s) that have been collecting dust – a double-breasted jacket, bold tie, or loafers – or a casual, deconstructed suit. No one likes a hardass, so don’t be afraid of a pattern or soft pastel, and remind yourself not to take the day (or yourself) too seriously.

View Oaks Day Lookbook

Stakes Day

Shop Calibre Men's Stakes Day Look   Shop Men's Stakes Day Look

For the races on November 10, the sartorial stakes aren’t very high (sorry). On Stakes Day, tailored separates will dominate the sea of mid-rank white collar professionals. There’s still the expectation to dress like you’re respectable, but feel free to experiment – separates in tonal colours, sneakers with your suit, or a knitted tie to substitute the more formal fare you’d see on Derby Day or Melbourne Cup.

View Stakes Day Lookbook

Related Article

The Ultimate Men’s Shoe Guide

The Ultimate Men’s Shoe Guide

A man’s shoes speak volumes and no closet is complete without a collection of shoe styles to see the discerning gentleman through the week.

Read More
The Finer Details: Suit Accessories

The Finer Details: Suit Accessories

The suit’s symbolic status as being a corporate uniform is being ditched. Fewer of us are wearing suits because we have to and more because we want to. So, w...

Read More
The Calibre Man’s Guide to Leather Jackets

The Calibre Man’s Guide to Leather Jackets

A leather jacket might just be the most satisfying garment a man can own. It lasts a lifetime, has timeless appeal and looks better with age.

Read More