For Tom Riley, head tailor at P. Johnson Tailors in Windsor, dressing well for the races is not about the outfit that turns heads – it’s the one that gets a second look, the one you can’t quite put your finger on why it looks so good. Most men have mastered the day-to-day business suit, but dressing for the Spring Races can be a much harder look to pull off. Some guys, excited by the opportunity to play outside of the grey scale, opt for bright colours or busy patterns – perhaps even both. It’s a look, Reilly says, more often than not misses the mark. “There are lot of guys that I think go a bit too caricature, it looks a bit comical—a bit twee,” he says.

The key is to aim for elegance but to go for a fresher, more leisurely style. “You lift it up a bit but you don’t go crazy, otherwise it looks cheap,” he says. Linens, cottons and other lightweight fabrics are better for warm weather and they also give suits a softer, more relaxed silhouette. Being out of the office and on the field also means there is a lot more scope to play around with colour – just remember to tone it back. “We sometimes make guys oatmeal coloured linen suits, or punchier colour cotton suits like a really strong blue or caramel or a sage green or something like that,” Riley says. “We’ve also been doing a bit of army green, which looks amazing. It’s really cool because it’s quite a masculine colour and looks interesting but is still easy to dress.”

Shirts are best treated as a background, says Riley (“If, say, you have a blue suit you might go for a slightly stronger blue shirt”), while you can have a bit more fun with ties. “You might go for a bit more of a saturated colour – rather than the muted darker tones – and maybe with some motifs on them so the look’s not too muddied and drab,” he says. “Going for a raw silk or linen tie can be amazing because then you get this beautiful soft, summery texture, which steers away from a business look.”

There are ways to add flourishes but Riley stresses that they should always be done in consideration of the entire look rather than just for the sake of it. “You might put in a pocket square—a pochette,” he says. “They can be your potent punch of colour. It’s a nice excuse to add a bit of asymmetry because sometimes if you look a bit plain and tidy it all looks a bit dull.” Popping a flower (each event has an official flower: a yellow rose for Melbourne Cup, a cornflower for Derby Day and a pink rose for Oaks Day) in your buttonhole is a nice touch and also shows respect for racing tradition.

Some guys might want to go for separates rather than a suit, which is a great look when done well, says Riley. “[Separates] traditionally suit an older guy but there are ways you can make it look sporty and fresh for a younger guy,” he says. His suggestion? Go for a really dark navy trouser and pair it with a light grey jacket and a middle-blue tie.

Adding different details can be tempting but Riley says things like cufflinks are hard to pull off. “Event or not, we view cufflinks as something you’ve got to earn,” he says. “We tend to think they look better on older guys who can manage more detail because of their face or hair or complexion.” The same goes for bow ties: “They draw attention to the face,” he says, “and suit the rounder face you get when you’re older.”

One of Riley’s major grievances is when guys leave shoes as an after thought. “Time and time again there’s too many bad shoes,” he says. “There’s no point having a lovely suit and ruining it with a pair of junky shoes.” Consider suede rather than polished black leather. A chocolate-brown, khaki, navy or snuff suede can all look great paired with the right outfit, he says.

There are some things that Riley says should never enter the racecourse. Bad sunglasses, ill-fitting suits (tight or baggy), overly structured jackets with thick shoulder pads, and coloured shoelaces are among his biggest gripes. “The key is to look at ease – you only pull it off if you look comfortable. It’s about harmonising all of the elements. If it’s not going to work, the trick is to not do it.”

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