Dressing for Cheltenham Festival and the Race Season 2020

Brown Tweed Suit Cheltenham Races

Suits for Cheltenham Races

March sees the return of one of the highlights of the British social season, Cheltenham Festival. The race results are not the only high stakes considerations for racegoers, Cheltenham festival is known for its fashion exhibition almost as much as its equestrian delights. 

As one of England’s premier sporting and social occasions with spectators coming from far and wide to enjoy the excitement, we would be remiss to not think about the attire for such an occasion.

Cheltenham Races

Image Credit: Racing tips

With The Henley House situated just 34 miles from the racecourse and in the heart of Warwickshire, we have been dressing spectators of the races for many years - as well attending on the odd occasion ourselves for a cheeky flutter! 

With four days of racing taking place between Tuesday 10th and Friday 13th March, regular and first-time racegoers are in for some extraordinary racing as well as incredible hospitality, shopping and entertainment! Cheltenham Festival is a unique experience among race meetings, especially because it has no formal dress code and yet the consensus is always to impress! 

Pete Wicks and Adam Cullord at Cheltenham Festival

'Pirate' Pete Wicks (TOWIE) & Adam Cullord (Love Island) - dressed to impress at Cheltenham Festival Photo Credit: The Jockey Club

Being mindful of the unpredictable British weather, dressing for Cheltenham races can be somewhat challenging, but it need not be! Not only does Cheltenham Festival present the finest in the equestrian world, but also the best in fashion and style can be seen across the four days - particularly on Ladies day. So, how can you stand out in the crowds of thousands? What should you wear to fit in with the best of British? How can you bend the rules of traditional racing fashion without going so far as to be escorted from the premises? Stick with us, The Henley House has the styling and fashion advice to see you looking your best, from the enclosures to the bars and back again!

lilac three piece suit

Above: Miami Lilac Slim Fit Three Piece Suit

Whether you are in the Best Mate enclosure, Tattersalls, a private box or you have splashed out for one of the Orchard Pods, which are new to Cheltenham Festival for 2020, The Henley House can help you dress for the occasion. The only thing you have to worry about is whether your Trixie is coming in and how many flurries you can have whilst leaving enough in the kitty for a jolly in the Magners and Guinness tents!

Lets jump in (pun intended!)...

jumps at Cheltenham Races

Image Credit: The Jockey Club

Is there a dress code for the Cheltenham Festival?

Officially no, but if you are holding tickets for the more exclusive enclosures there may be specific requirements. Although there is no formal dress code it is something of an unwritten rule that smart attire is preferable, particularly during Ladies Day and the Gold Cup final day. That being said, smart doesn't have to mean stuffy!

The Henley House at Cheltenham Races

For a chic look with a difference, why not mix-and-match pieces? We love the pairing of a bold coloured chino or suit trouser with a textured jacket and statement coat. The key for this look is to have a focal piece and the rest of your look should draw on the same colour palette. An elegant dress scarf is a great way to add some personality to your look whilst also keeping the sharp chill off your neck!

Tweed is King at Cheltenham Races!

When we think of horse racing fashion we think tweed...and for good reason! Not only is tweed a nod to British heritage and country attire, but it also has practical applications! I know, I know… when it comes to fashion no-one cares about the practicalities,  but considering the British weather in March you may be thankful of the warmth of tweed and the propensity for tweed to be worn in layers, meaning whilst at the post you will stay warm but when you're at the bar you can remain looking dapper without getting a sweat on! Leave that for when your horse is ‘going to the knackers’ or when you've called a blinder but can't find your slip!

Above: Albert Brown Tweed Suit

Speaking of ‘blinders’, the brummy troublemakers have given a new lease of life to men's tailoring, especially of the tweed and heritage variety! Making ‘peaky blinders’ styling not only on-trend, but also a genius blend of traditional sartorial tweed with a modern twist. With updated tweed colour and patterns with contemporary cuts mixed with the right accessories you can achieve a look sure to be sported by the Shelby boys whilst watching Monaghans Boy! 

Above: Connall Navy Tweed Check Suit

Above: Albert Grey Check Tweed Suit

There is a huge array of tweed available, here's but a few to whet your whistle:

Barleycorn - This is a fun approach to tweed, typically a course weave which creates the effect of barley heads when viewed up close.

Checked - This is a very popular tweed which is fairly self-explanatory. For a modern take on checked tween opt for a larger overcheck in a different colour to the base tone. 

Houndstooth - sometimes called dogtooth, this print is a classic and is said to resemble Rex's back teeth!


Plaids & Tartans - For those of Gaelic origin this can be a nice nod to your heritage.

Herringbone - Another design with animal origins, Herringbone resembles fish bones as you may have ascertained from the name. Herringbone tweed is created with multi-directional weaves creating a V shape. This is one of the most popular tweed styles along with checked tweed.

Twill -  This is a simple diagonal weave which creates an attractive texture and pattern to the cloth.

Overcheck Herringbone - This consists of herringbone weaving overlaid with a contrasting check and is a traditional Estate Tweed. Fancy! 

Overcheck Twill - Basically as above but with twill as the foundational pattern. 

Striped - Again, the name kind of gives this one away. Striped tweed is made up of vertical strips in various sizes to create the striped design.

All patterns have their own statement look and characteristics but ultimately are created using tweed fabric. The choice of pattern is dependent on the look you wish to achieve. Tweed is a staple in anyone's wardrobe, year in and year out and is a classic look for the races. Modern twists on tweed are ever popular and you are sure to find a tweed suit that works for you with The Henley House.

Find a Winning Look - Men's Race Day Attire

If tweed isn't your thing, there are plenty of other options available! Go fully suited and booted in the best of 2020 styling or mix and match pieces to create your race day look! 

Above: Sky Blue Double Breasted Slim Suit

Double breasted suiting is going to be huge in 2020, like this stunning blue three piece with double breasted waistcoat. 

Whether in attendance for the Champion Hurdle and opening day delights, The Queen Mother Champion Race and the competition to crown Miss Cheltenham on Ladies Day, the craic of day three and the Stayers Hurdle, or the pinnacle of Jump racing with Gold Cup day held on Friday 13th March 2020 (unlucky for some!), there’s a look for all and sundry! 

Above: Seeba Navy Three Piece Suit

Go sleek and chic like a thoroughbred with a simple two-piece styled with a statement turtleneck and subtle pocket square.

Ladies Day isn't just for the fillies and there's no need to rein in your sartorial prowess. So go big with a bold, statement piece or step out in a stunning three piece fully decked out with ’on-brand’ accessories.

Above: Callie Grey Check Slim Suit

Unleash your inner stallion with a statement print and pop of colour, layered with a neutral overcoat and Chelsea boots! The double breasted scoop waistcoat is a statement in and of itself, and will ensure that you continue to pack a sartorial punch way into the after-party!

Get the Local Look

With a strong equestrian identity in and around Cheltenham, with huge names in the game training and riding locally, take a leaf out of the books of Jonjo O’Neill (all about that fedora and wax jacket!), Nigel Twiston-Davies (a sucker for a great coat and layers) and Fergal O’Brien (rarely seen without his trademark tweed flat cap) and take country attire to the next level!

The Henley House can kit you out from Hoof to Forelock...

Cheltenham shoes

Left to Right 

1. Mandu Tan Casual Brogue

2. Sherlock Navy Lace Up Boots

3. Horatio Brown Tweed Brogue Shoes

4. Westland Tan Chelsea Boots

Accessorise like a boss with a range of shoes, boots, hats and coats and keep your look fresh whilst remaining comfortable and warm throughout the whole of the Cheltenham Festival. 

 Cheltenham hats

Left to Right

1. Blue Herringbone Peaky Blinder Hat

2. Albert Brown Check Flat Cap

3. Olive Peaky Blinder Hat

Look good, feel great, win big and experience all the fun and sense of occasion that the Cheltenham Festival brings! When else can you pull out your inner country gentleman, get dapper 'peaky blinder' style, or dress to impress whilst popping a few bob on the Geegee's?

Whether you feel the 'need for tweed' or are chomping at the bit for a three piece, The Henley House is the place to visit ahead of Cheltenham Festival and the start of the race season!