Cheltenham 2020 – Tips for your wardrobe and wallet.

As in now tradition, I’ll be off to Cheltenham this Friday, for what is undoubtedly the greatest day of the racing calendar. I’ll be honest, my interest in racing has waned slightly over the last year… but with the festival round the corner, it doesn’t take much for me to be picking up The Racing Post again.

A day at the races is a good opportunity to not just watch some first class racing and a few beers with your mates but also to look your best. So this year I’ve put together another blog with my thoughts on what to wear at the festival. Like anything, horse racing suffers from cliches and the popularity of Peaky Blinders. At race courses over over the land you’ll now be hard pushed to find a lad who isn’t wearing a flat cap or baker boy. You’ll be equally hard pushed to find a pair of socks on display.

So with that in mind, I thought I’d try take look at some options to help you stand out a little bit whilst still in keeping with tradition and practicality.


If you want to really go all out and ensure you look the part in the Champagne bar, whatever you have in your pocket, then you’ll probably be plumping for a suit. Despite the signs of Spring being here, Cheltenham is nortoriously cold and windy so I would go for a good quality wool suit. If you have the budget, this Windowpane Check wool suit from Hackett is perfect.

Or for a slightly smaller budget this cashmere wool Milan suit from Reiss, in grey would do the trick.

Smart Casual

If you feel like a suit is a bit much, which I do, then you’ll want to look smart but a bit more casual. My advice here would be to not go over the top, classic is the key. A nice pair of smart trousers, and you can’t go wrong with a pair of classic Farah chinos.

Farah Chinos

Then you’ll be looking for a smart shirt. My preference is always for a classic Perry, of which I have many, and for some reason I tend to favour a check for Cheltenham. But a classic Oxford will do the trick if you want something a bit lighter on the wallet, from ASOS or Original Penguin.

As I touched on, despite it being mid March, it’s often pretty chilly at Cheltenham so with a smart shirt you’ll want a nice jumper. I tend to go for a nice half zip. Something from Ralph Lauren is perfect, or for a cheaper option Burton does the job.

Alternatively you could fall in line with the country gent look and go for a gilet. I personally have always steered clear of “the farmer’s vest.” There are too many connotations of Rugby and London Pride farts for my liking. But if you avoid Cotton Trader, there are options out there from the menswear stores who know the score, like Hip Store.


The rise of the loafer and no sock brigade has not exactly been welcomed at race courses round the country over the last few years. Don’t get me wrong, there is a time and a place for a nice loafer and a bare ankle, namely with a pair of tailored shorts on strolling down a promenade or sat with an sipping an espresso observing a beautiful piazza.

Cheltenham however, is not the place. Weather is often not great and just making it through the car park would ruin a pair of Topman tassles. So if you have plumped for a suit then a decent hard wearing brogue is probably your best mate. Or if you have gone a bit more casual, a smart Chelsea boot or something similar.

For something a bit different but stylish and durable, try something like a Red Wing boot from the likes of Hip Store.

Coats & Hats

A decent overcoat is essential and it’s best to go with something warm and smart, like this wool blend overcoat from REISS.

In terms of head wear, despite my love of Peaky Blinders the TV program but hatred for what it has done for the flat cap, they happen to suit me and I maintain I have been wearing one well before Tommy Shelby appeared on our screens and will be long after he has gone. So I’m sticking with it. ASOS have a decent enough range.

Tips For Your Wallet

I am by no means a horse racing expert and would never claim to be a “tipster” but here are a few of the horses I might have a couple of quid on at the festival. Gamble responsibly!

Tuesday: 2:10 Arkle – Cash Back.

On Friday: 1:30 Triumph Hurdle – A Wave of the Sea. 2:50 Albet Barlett – The Cashel Man (EW) 3:30 Gold Cup – Presenting Percy. 4:10 Foxhunter – Minella Rocco

See you in the Champagne bar…

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