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How to Dress For Cheltenham – Men’s Guide
It’s one of the biggest events in the horse racing calendar, and that’s why you’ll want to ensure your outfit for Cheltenham is a winner. One of the most important…
Mar 6, 2018
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It’s one of the biggest events in the horse racing calendar, and that’s why you’ll want to ensure your outfit for Cheltenham is a winner.

One of the most important events in the horseracing calendar, the annual Cheltenham Festival (13-16 March) is looming large on the horizon. The three-day event is as renowned for its fashion as its fillies, so for those attending, it’s important not to let the sartorial side down.

As with any race meet, Cheltenham presents the perfect opportunity for men to showcase their personal style, whether it be discreet or daring. Thankfully, there are no hard and fast rules to men’s racing fashion, but it’s a given that those attending will make an effort. And that’s why it’s important to get your outfit right and look your best, even if your horse comes in last.

Whether it’s a natty blazer-and-trousers combo, a razor-sharp contemporary suit or something in the more traditional tweed (the fabric most commonly associated with racing), there’s a wealth of choice for the style-savvy man. Whatever your preference, though, it’s important to get the basics right. The following tips will ensure that, regardless of whether you go traditional or contemporary, you pick a winner – every time.

CHELTENHAM CLASSIC SUIT

If in doubt as to what to wear, you’ll not go far wrong with a classic suit. It’s a failsafe option that works for men of all shapes and sizes, and it won’t require much if any, additional expenditure.

However, while your basic business suit-and-tie combination will be perfectly adequate, it’s not exactly going to mark you out as a man of style. Work suits tend to be slightly dull and, most likely, dark, so you’ll blend in the crowd, rather than stand out.

Colour-wise, a deep blue or navy suit will take you anywhere, whether it’s the VIP tent or the queue for the bookies; and is a resoundingly safe yet stylish choice. Its versatile shade and clean finish mean it can be dressed up and down, depending on your mood, giving you a look that’s elegant but not overpowering.

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CHELTENHAM THREE-PIECE SUIT

For a more dapper alternative, without venturing too far from your style comfort zone, it’s hard to look beyond a three-piece suit. The addition of a waistcoat adds a subtle sartorial flourish as well as a handy extra layer for insulation (Cheltenham is not exactly known for its balmy weather, so any extra padding is always welcome). And should you remove your jacket, it will ensure that you still look smart in your shirt.

If you decide that three really is the magic number, you can go as bold or simplistic as you want, opting for a busy patterned suit or, conversely, a plain coloured one. Just take care to ensure the waistcoat is as well fitted as your suit, that it is long enough to cover your waist, and, crucially, that you always leave the last button undone.

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CHELTENHAM PATTERNED SUIT

For something distinctly different and, possibly, daring, a patterned suit will tick all the boxes for racecourse style. From windowpane check to classic houndstooth, there’s a wealth of choice, whatever your budget, making the patterned suit a great choice for the modern dandy.

Worn well, a patterned suit can look peerless. The scope for error, though, is enormous. Unlike its plain counterpart, the key when wearing a patterned suit is to keep the focus on the suit itself, rather than visually complicating the look with a bold shirt colour or a tie in a clashing print.

Instead, keep it simple and stick with a classic white or blue shirt, which won’t reduce the impact of the suit, but will ensure that you don’t detract from its pattern. Race fashion is, of course, all about being different and creating a look that is stylish yet personal – but you want to stand out for the right reasons.

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CHELTENHAM TWEED

Don’t dismiss tweed as a drab choice – the classic fabric has been reinvigorated by some of the best men’s fashion designers and can really look the part, especially at Cheltenham.

While a tweed suit is typically associated with the classic country gent, there’s a great selection of designs with a contemporary slim-fit that look the business, particularly when styled and accessorised correctly.

The classic tweed is, of course, a variation on the distinctive patterned squares and green colouring; but today’s tweed comes in a number of shades, colours and patterns. If green holds little appeal, why not consider a stylish grey?

Whatever colour tweed you opt for, be sure to personalise the look with a shot or two of colour via your tie and pocket square.

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CHELTENHAM SMART TROUSERS & BLAZER

So long as they’re smart and immaculately fitting, teaming smart trousers with a blazer is a perfectly acceptable dress code for Cheltenham, or indeed any racing event. It’s worth making a bit of an effort, though; so if you decide the venture down the blazer-and-trouser route, why not try wearing something a little different to your usual style?

A double-breasted blazer makes a stylish and elegant alternative to the more conventional single-breasted designs, which will be ten a penny at Cheltenham. Cashmere, tweed or heavy cotton will all give you a distinguished look.

More conventional but still classy is a plain navy blue blazer, ideally with brass buttons - a classic look that never dates. It can be worn with or without a tie, although for Cheltenham we’d always recommend the former.

Regardless of whether you go for a single- or double-breasted blazer, your choice of trousers is key to the look. Smartly pressed, slim-fit chinos (cream is a safe choice, while red is distinctly dandy) with a low rise are hard to beat. Alternatives include moleskins, cords or flannels, all of which are, if you’ll pardon the pun, safe bets. Just make sure that your trousers are an obviously different colour to your blazer to avoid looking a mis-matched suit.

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CHELTENHAM OVERCOATS

The weather at the Cheltenham Festival tends to be cold, damp and unpredictable, so an overcoat can be a smart choice. While function is paramount, this should not be at the expense of form, so make sure your coat complements the rest of your outfit.

Classic styles such as a Chesterfield or a Covert will always look the part, ensuring your look is still smart while also keeping you warm. For a more contemporary alternative, consider a trench coat, which is wonderfully versatile and will sit perfectly over a suit or blazer.

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CHELTENHAM ACCESSORIES

Even if you’ve got an ultra-sharp suit, there’s no reason that it can’t be improved with a few well-chosen pieces. At Cheltenham, men typically go traditional with their accessories (remember: less is more) and restrict them to items such as pocket squares, bow-ties and, less commonly, tie or lapel pins.

If you’re planning on wearing a plain suit, there’s more scope to play with your accessories – you can be more adventurous with the colour and print of your tie (or bow-tie) and pocket square. If your suit is patterned, though, don’t over-complicate the visuals: keep the accessories as simple as possible, ideally in neutral colours to avoid any unsightly clashes.

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CHELTENHAM FOOTWEAR

If you’re going to the trouble of sourcing the perfect race outfit, it’s vital that your footwear doesn’t let the side down.

Acceptable footwear comes in various forms, depending on your personal style and your outfit on the day. It should be smart, however, so that rules out trainers, even if they’re trendy black leather.

In terms of shoe colour and style, aim to match your footwear with the rest of your outfit. If you’re going for a suit, consider a classic and conservative option such as Derbies or a pair of plain black (or brown, if you’re wearing navy) Oxfords. Brogues and wingtips are two alternatives, both of which will ensure you keep the tone of the outfit smart yet slick.

If you plan on wearing a blazer and trousers, there’s a little more leeway in terms of choice. Penny or tasselled loafers are a great smart-casual option, while suede brogues will add a rakish touch.

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So there you have it. Whether you’re a straight-up suit-and-tie man or a daring dandy that wants to flaunt his fashion feathers, dressing for the Cheltenham races is the perfect time to have some fun with your wardrobe and create a personal look that will raise glasses, rather than eyebrows.

Looking for more tips and advice? Check out the How-To and Style sections to keep up with the latest trends and improve your style game.

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