A Day at the Races: a complete shoe guide for three racing events
If you’re planning a day at the races but are not sure what to wear, we have curated the ultimate guide. Let us help you to avoid any fashion disasters and look the part ready for race day.
Horse racing is the perfect opportunity to show off your personality through fashion, add style and colour to your outfit, and is a great excuse to get dressed up. So whether you’re attending Ascot, galloping to the Grand National or darting to Cheltenham, here at Cheaney, we’ve picked out our best shoes to pair with your men’s races outfit that’ll have you winning the style stakes.
Table of contents
- What shoes should men wear to races?
- The Grand National dress code
- Royal Ascot dress code
- Cheltenham dress code
What shoes should men wear to races?
Your horse race day shoes will depend on a few factors; the weather, the dress code and comfort. Firstly, your comfort is paramount. A day at the races is long, and you want to ensure your feet aren’t blistered and sore by the end. Make sure you wear-in any new shoes before race day.
Secondly, when choosing your race day shoes, consider all weather outcomes. You can opt for a monk shoe for spring. But when it comes to summer events, you can swap them for a more open loafer.
Lastly, different race events require varying dress codes. For example, The Cheltenham Festival has no official dress code, meaning you could wear trainers and joggers, as there is no limit. However, an event like Royal Ascot has strict dress codes, so ensure you read these carefully before turning up or risk not getting in.
The Grand National dress code
With the next Grand National race happening on the 15th of April, 2024, this springtime racing event is a fantastic opportunity to wear bright and bold spring colours. Wear a bright suit; or a plain suit with a jazzy tie to stand out. Race day is a great way to get creative with formal wear, injecting fun into your everyday office suit.
With no strict official dress code, The Grand National gives you a perfect chance to mix and match. Try switching around your jacket and trouser colour combinations to create that modern race-day feeling. A few variations could be a navy tweed jacket with grey, beige or tan trousers. Alternatively, a jacket in a light shade of cream or beige with navy blue trousers or vice versa. Complete your outfit with a pair of penny loafers, a classic choice for spring/summer to help you achieve that effortlessly elegant look. Don’t forget to add something extra-special for race day, like novelty cufflinks or a colourful tie.
The shades of your attire will determine which colour to opt for shoe-wise. Using the colour scheme below as an example, we recommend pairing various beige shades and pastel tones with the Hadley Penny Loafer in Burnished Dark Leaf Calf Leather. This colour combination isn’t classically matched but creates a bolder statement for something different.
If you’ve chosen a grey check suit, don’t play it safe with a pair of black or brown Oxfords. Stand out from the crowd and inject colour into your outfit with York, capped Oxford in Burgundy Calf. Add the finishing touch and tie the outfit together by ensuring your tie matches your shoes.
Royal Ascot dress code
With the next Royal Ascot just around the corner on the 18th-22th of June 2024, you have plenty of time to decide what you’re wearing. The Royal Ascot dress code is strict because of its prestige and royal associations. Furthermore, there are four enclosures, each with a different dress code.
If you are in the Royal Enclosure, you must stick to a traditional morning suit in either grey, navy or black. You can only wear black shoes, but any of our black Oxford shoes are perfect for this occasion. Our Oxford styles are available with a Dainite sole. Instead of traditional leather soles, it features a subtle rubber base to help keep your footing.


Bring your A-game to the Queen Anne Encloser by opting for a navy suit; stylish and versatile. A blue slim-fit suit is a winning outfit. In this enclosure, you must wear a formal day-wear two or three-piece suit with all matching materials and colours.
Navy suits coordinate well with most shoe colours. However, in our view, we think they go best with a darker shade of brown, and our Tudor Double Buckle Monk Shoes in Espresso Calf are the perfect match.
The Village enclosure is a lot more relaxed. You can choose a suit or blazer, trousers or chinos, with mix and match colours. Why not pair your mix-and-match ensemble with a two-tone brogue? Our Edwin Two-Tone Oxford Brogue in Chestnut Calf and Navy Suede would pair well with a mixture of browns and blues in your outfit. These offer the perfect combination of formal dress and creative personality.
The Windsor enclosure, like the Cheltenham and Grand National, does not have an official dress code, but they encourage you to dress smart. The Windsor enclosure gives you the opportunity to be creative and branch out with colours, textures and styles. Wear something out-of-the-ordinary and make a bold statement with a bright suit and our Carlton Derby Brogue in Rosewood Rub off Leather.
Cheltenham dress code
The Cheltenham Festival is next occurring on the 12th-14th of March 2024, so you have plenty of time to curate your outfit. Recently, the Cheltenham Festival organisers ditched the traditional formal dress code to make the festival more inclusive. Although, they state that it is the “perfect occasion to wear your best outfits and favourite accessories.”
If you’re a stickler for tradition, you won’t be alone in still sporting a three-piece suit at the Cheltenham Festival next March. As the Festival is in March, the weather can be unpredictable. So, we recommend something warmer, like a green tweed suit with a matching tweed flat cap.


Set in the idyllic Gloucestershire countryside, now is the perfect time to get out your country-style formal shoes and matching tweed suit. Anything from our Country/ Leisure collection will work perfectly. But, our personal favourite shoes to pair with a tweed suit are the Avon Derby Brogue in Almond Grain Leather or Tenterden Derby Sem-Brogue in Mahogany Grain Leather. The decorative broguing, grain leather and derby style provide a more causal feel to your outfit while remaining formal for the racing event. The earthy tones of these two styles will pair perfectly with your green tweed suit.
The derby style shoe is well known as a more casual style than the Oxford, so this style perfectly caters to the updated Cheltenham dress code while still looking dressed up. You will also find these shoes provide more wiggle room for comfortable all-day wear.
Horse race day shoes at Cheaney Shoes
Whatever horse racing festival you intend to attend in the next 12 months, you won’t have to worry about footwear here at Cheaney. With hundreds of styles, designs and colours of men’s shoes, you have many choices for your formal dress. Our men’s shoes are the perfect horse race day shoes for any strict or smart-casual outfit. Why not browse our men’s shoe collection today? Don’t forget to add the finishing touch to your attire with our range of matching belts, all handmade in England.
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