💥🐎 Are you ready, for the Cheltenham ROAR?! 🐎💥

With the Cheltenham Festival under 4 weeks away (I can’t believe Gold Cup Day is 4 weeks today!) – I thought now was the perfect time to cover the ultimate racing footwear blog – with a little help from my favourite footwear brand – Fairfax & Favor!

There really is something for everyone in this blog. So whether you’re searching high and low to treat yourself to the perfect pair of boots, or looking to pair an outfit with the boots you already have – whatever your situation, this blog has you covered!

Cheltenham Festival doesn’t have a set dress code, however, most people opt to dress up in smart Country clothing. The beauty of Cheltenham is that you can dress in what you feel most comfortable in. Something important to bear in mind though, it is usually C-O-L-D at the racecourse! Even on those days which may feel a little milder, Cheltenham still has its own weather – so do keep this in mind when you’re planning your perfect outfits.

If you want to have a look at outfit ideas – check out my racing page from my blog homepage, which will link you to all of my previous racing blogs! There is a lot of inspo already on there!

When it comes to your footwear choices, keeping the weather in mind is also key! Unlike the Grand National and Royal Ascot, you don’t really need to wear heels, unless you want to! Most people will be seen in boots – suitable for tackling wet grass and muddy walkways. Comfort is key for a day at the races too – you are likely to be on your feet most of the day, and there is nothing worse than a pair of shoes pinching or rubbing – it’s all you can think about and it has the potential to spoil your day!

A couple of top tips – take plasters anyway, hopefully you won’t need them, but your friend might! If you’re opting for a new pair of shoes or boots, break them in before hand so it isn’t the first time you’re wearing them on the day! ALWAYS protect your leather and suede boots before wearing, I keep saying it, but at Cheltenham it is likely to rain or at least be muddy at some point, and you don’t want to risk spoiling your footwear. Know your plan for the day, if you’re planning on walking around and standing all day, make sure you wear footwear suitable for this. And lastly – wear something you love – this is one of the most amazing days/weeks and you want to enjoy it, wearing something you feel comfortable and confident in!

I’ve said it before on my blog, and I’ll continue to say it again, one of the best things you can invest in within your wardrobe, is your footwear!

So, let’s get into this blog!

– Tall Boots –

The most perfect place to start when it comes to racing footwear. The classic, timeless elegance of a tall boot makes for perfect racing attire, and is versatile enough to go with any style of outfit you choose. With both leather and suede options available, you can be covered whatever the weather! Tall boots have an innate ability to transform outfits, they are the confidence giver of footwear, and usually comfortable and easy to break in! They pair well with absolutely everything, so whether you’re opting for your favourite dress, a new skirt, or a trusty pair of comfortable trousers, tall boots are a fail safe option to go for!

The Regina

The iconic Regina, how could this not be first up! A racing staple and the official ‘uniform’ of Cheltenham Racing outfits is it not?! The Regina covers all bases that you could want from a boot. Whether a slight heel is your style, or you want something leather and practical, the Regina is the go to boot of all Cheltenham outfits.

The Regina comes in suede or leather so you can opt for whichever option works best for you, the good thing about both is that they break in very easily, so if you have a new pair they are not likely to need much wearing in prior to the day.

One of the most easily recognisable characteristics of the Regina, are of course the interchangeable tassels. This can make a considerable difference to your outfit, and nothing beats the confidence that comes with that tassel swish. There is such a vast range of tassels available, and you can pair these to match a statement or main colour of your outfit. Another great way to tie your tassels into your outfit is to pick out one of the more subtle colours in your outfit, and match a pair of tassels to this colour. This will help to pick up that colour in your outfit, and make it a subtle focus!

Available in a wide variety of colours; Flat, Heeled and High Heeled options; and narrow, Regular and Sporting Fit calves.

CCL recommends wearing with: absolutely anything!!! Why not team with jeans, a simple roll neck, a jacket and fedora for an iconic country style, a dress and long time jacket with a fascinator for Ladies Day, or team with a matching skirt and jacket combination for Gold Cup day! The options are endless!

Find the Regina boots here.

The Upton

Brand new for Autumn/Winter 21/22, the Upton is both practical and stylish – the best of both worlds for Cheltenham. I think this boot has a really simple, but obvious, Country elegance to it.

Featuring a 7cm block heel, The Upton gives you an elegant lift, whilst still being comfortable and practical for a full day on your feet. Full leather is a great option for unpredictable weather days as they clean up well. Don’t forget Cheltenham can get muddy and grass is almost unavoidable!

I have actually tried the Upton at a trip to F&F HQ and I couldn’t believe how comfortable the boot was. Out of all of the collection, I think this is the boot where I physically remember going immediately ‘Wow they are SO comfortable’! I don’t know if I was expecting them to be a little more stiff being leather – but if you would have thought the same, I can comfirm they feel butter soft when you slide your foot in!

Available in Mahogany and Black Leather

CCL recommends wearing with: classic green tweeds! The Upton is the ultimate leather boot to dress up any outfit. Team with a green tweed skirt or jacket, and natural earthy tones for the perfect Country elegant look.

Find the Upton boots here.

The Soho

Another new item from Fairfax & Favor for A/W 21/22, and this is a really special one! The sublime elegance of the Soho is something else. With a slightly higher 8.5cm heel compared to the other boots, the Soho elevates and flatters, but comfortably, with the memory foam insole making these boots wearable all day. I would say, the Soho does feel high compared to other F&F boots if you’re like me and not used to wearing heels much! They are comfortable and supportive though and do feel really special with that increased heel height!

Cutting off at the knee, and with a pointed toe, the Soho offers a modern take on a classic day to night boot, perfect for a day at the races, followed by drinks in Cheltenham town itself. The full zip at the back has interchangeable tassels, perfect for adding the finishing touch to your outfit. This is a subtle way to compliment colours throughout your outfit, in a classy way.

The Soho is the perfect boot to take your outfits from casual weekend to Cheltenham ready. This has become one of my favourite boots, and with the classic colour way options, these will easily pair with a variety of outfits!

Available in two staple colours – Black & Tan.

CCL recommends wearing with: your favourite dress or skirt, opt for neutral tights if you wear the tan, and black tights if you’re wearing the black boot.

Find the Soho boots here.

The Belgravia

The Belgravia knee high has been curated as a ‘go-to’, easy to style, and easy to wear boot. Crafted from soft stretch suede, the Belgravia will streamline your outfit, creating a sleek finish to your look. Without bulk, the Belgravia offers a close fit, which is both smart and elegant when paired with dresses and skirts, or trousers.

The classic colour ways available make the Belgravia an easy choice for any race day outfit. Boots which have a close fit work well with trousers for a well put together, smart look. When paired with a dress or tights, the Belgravia will instantly lift your outfit in elegance. For close fit boots like the Belgraiva, opt for tights which match the colour of your boots. This helps to continue to streamline your outfit, without colour separation.

A 6cm cuban heel offers an elegant lift, without the difficulty of navigating a heel all day, perfect for the races!

Available in Tan, Chocolate, Black and Navy.

CCL recommends wearing with: a fit and flare dress for Ladies Day elegance, or trousers and a long line fitted jacket for a classic country style.

Find the Belgravia boots here.

– Over the Knee Boots –

An easy way to elevate your outfit is to go for an over the knee boot. This is so commonly my choice of boot for a day at the races, they look smart, are comfortable enough to wear all day, and the F&F over the knee boots all come in really easy, practical colours. Adding a long silhouette to your outfit, over the knee boots are a really easy way to dress up any trousers, skirts or dresses.

The Amira

The Amira still holds one of the top spots for me in my favourite F&F boots. Whilst a practical boot, the Amira is classically F&F, with its tasteful shape and iconic interchangeable tassels. There is something sassy about the Amira, I feel like I strut, not walk, when I wear them. They give off a confidence to an outfit which makes you feel like a queen.

This style of boot is a great option for the races, whether you decide to pair with trousers or a skirt or dress. If you’re opting for the black boots, use black or darker colours as a theme to tie in to the rest of your outfit, and if you opt for Tan, use more neutral tones for the theme of your outfit. With your over the knee boots being a large part of your outfit, this helps to tie your outfit together seamlessly!

With a flat option as well as a 7cm heeled option, there is something suitable for every style.

Available in Black and Tan, with heeled and flat options.

CCL recommends wearing with: a tweed skirt, dress or full length trench coat. The Amira was born to be shown off. Teaming with a dress or skirt allows the Amira to speak for itself, whilst teaming with a trench coat, you opt for complete elegance within an outfit.

Find the Amira boots here.

The Brompton

A slightly different take on the over the knee boot to the Amira. The Bromptons ooze an understated elegance, perfect for subtly elevating your outfit – F&F style! Similar to the Belgravia, the Bromptons create a sleek silhouette, which works particularly well if you are wanting to opt for trousers or jeans, without too much of a dressed down feel.

Designed with a heel, but with the help of the classic F&F comfort insole, the Bromptons allow you to experience the lift you gain with a small heel added to your outfit, without the discomfort or difficulty or enduring a day in heels.

CCL recommends wearing with: white or black jeans, a roll beck jumper, your favourite long line jacket and a fedora with statement hatpin.

Available in Black or Tan.

Find the Brompton boots here.

– Ankle Boots –

The Kensington

The OG when it comes to F&F ankle boots, the Kensington combines both suede and leather to create a country chic boot.

With a 7cm heel, the Kensington sits nicely between the range of F&F heel heights, offering a comfortable lift. The memory foam comfort insole ensures these boots remain comfortable all day.

The Kensington was my go to ankle boot for many years, being both comfortable enough to wear all day, whilst adding a smart casual option to your outfit. With the 3 classic colour options, you can easily pair these boots with your favourite dress for Ladies Day, or why not try with a green tweed for a classic Country look.

Available in Black, Tan or Chocolate.

CCL recommends wearing with: a midi dress for Ladies Day or teamed with jeans or a skirt for a classic Country look.

Find the Kensington boots here.

The Ankle Regina

My favourite ankle foot from the F&F collection, there is something so regal about the Ankle Regina! With a pointed toe, arched heel and scalloped edging, the Ankle Regina offers a smart, tasteful short boot alternative for your race day styles.

Easily paired with all styles of outfit, the Ankle Regina will finish off any look with its understated beauty, subtly nodding towards its older sister in the iconic F&F Regina boot.

Available in Tan, Black, Navy or Chocolate.

CCL recommends wearing with: black or white jeans, a longer line jacket in the same colour as the boots, and a matching fedora.

Find the Ankle Regina boots here.

The Belgravia Ankle Boot

The little sister to the Knee High Belgravia, the Belgravia Ankle boot offers the same soft stretch suede, which forms to your leg, creating a beautifully tailored look. This design is for you if you find that ankle boots can often look a little clumpy at the end of your outfit, or a little out of place.

With the taller design of the Belgravia Ankle Boot, these run seamlessly into your leg, creating an effortless silhouette, to maintain this with skirt and dress outfits, utilise tights in the same colour as your footwear.

The Belgravia Ankle boot does feature an 8.5cm block heel. Whilst this is a little higher than most of the other boots, this lift can be just the hybrid between boot and heels you may be looking for for your race day look. A block heel is a great option for the races, not only for ease and comfort, but also for walking on grass!!!

Available in Black or Tan.

CCL recommends wearing with: a full length trench coat, or a skirt or dress outfit!

Find the Belgravia Ankle boots here.

– Shoes & Loafers –

For those of you wanting to opt for a loafer or high heel instead, well, we have you covered there too! Whilst Cheltenham has no set dress code, and you certainly won’t look out of place without heels to your dress, it is an occasion to dress up, and for many, pairing your outfit with a pair of heels is that final finishing touch.

The Apsley

The Apsley are a stylish, smart take on a loafer – perfect for the races when you may not want to wear boots, but want to opt for a smart shoe. Loafers are considered a staple in the Country wardrobe, and certainly won’t look out of place at the races.

Just like the F&F boots, these loafers come with a comfort insole, perfect for being on your feet all day.

I highly recommend with loafers that you match your tights colour to your footwear when wearing a dress or skirt. To elongate your legs, and help with a seamless, effortless silhouette, keep your tights natural if wearing Tan, Black when wearing Black, and Navy when opting for Navy footwear. If you wear black tights with tan shoes for example, you begin to break up the outfit, causing blocks of colour to segregate your final outfit.

Available in Tan, Navy and Black.

CCL recommends wearing with: a dress for skirt on Ladies Day for a practical alternative to a pair of heels. Or team with black or white jeans, tweed blazer, shirt and fedora for an effortless Country style

Find the Aspley loafers here.

The Daisy

Whilst Cheltenham Festival doesn’t have quite the same dress code as the likes of Royal Ascot, or The Grand National, Ladies Day is a great opportunity to grab a dress, and dress up! I have to add a warning with heels when it comes to Cheltenham. Don’t forget we are in Winter months, and usually the ground will be damp and muddy – this is pretty much unavoidable at the racecourse. If you are in hospitality, a box, or not planning on straying too far from the bar, heels are likely to be a more achievable option, than if you are wanting to walk around all day, and be up close to the action.

The Daisy is the perfect heel for the races due to its block heel and ankle strap, offering good support compared to a stiletto heel.

These are so beautiful, I really wish I had a pair of these for Ladies Day this year!! They would have been my choice!

Available in two classic colour ways – Tan/Navy and Navy/Red.

CCL recommends wearing with: a dress and long coat for Ladies Day. Team with a fascinator in matching colour way for a flawless, elegant outfit with the wow factor!

Find the Daisy heels here.

– Gallery –

There’s still lots of racing content to come on my blog, Instagram, and social media channels, so make sure you stay tuned in the lead up to The Festival.

I am also currently running a series of giveaways over on Instagram, to win pieces I use to create my dream outfit! Every Monday in February I am launching a brand new giveaway, and I have the most dreamy pieces that you can win, there’s one running at the moment – head over to Instagram to enter! Ps… If you enjoyed this blog – you may want to check out my giveaway live at the end of this month (hint hint!!).

If you don’t want to miss any of my upcoming blog posts – don’t forget to subscribe below!

See you next time my darlings 🤍

Lots of love, Lucinda xo

“You can never take too much care over the choice of your shoes. Too many women think that they are unimportant, but the real proof of an elegant woman is what is on her feet.”
— Christian Dior.

Please note I do have an ongoing working relationship with Fairfax & Favor, but this specific blog was not produced as part of a collaboration. All information was correct at the time of publishing. No links within this blog post are affiliate links.