What to Wear to the Cheltenham Races

I went to a superb point-to-point last weekend, which put me in the right frame of mind for the Cheltenham Festival. Resulting from extensive conjecture, I now have my fancies for sporting wagers during the festival. The wagers will include straightforward place bets, but introduce a strategic full cover bet for Gold Cup day. I will undoubtedly change my mind about my picks on the day.

Circle your winners
A sporting country look is the order of the day at Cheltenham (as opposed to, say, toppers at Royal Ascot). Something like the external rig below will see you right. Just add a tweed suit, decent binoculars for race viewing, a copy of the Racing Post and a Conway Stewart fountain pen to circle your winners, and you're good to go.

Racing Green Trilby

Gotcha! You fully expected a brown trilby for race day. Let's mix it up with this lovely medium-brimmed fur felt trilby from Christys' in British racing green. Wear the brim up at the front or snap it down, depending on your mood and the outcome of your bets — often related.

Nice enamel race badges
You may wish to tuck the race meeting badge in the hat band. I saw some old enamel race badges for sale recently. They are so much nicer than the cardboard type. I should have bought them, thinking about it.

Double-Breasted Tweed Overcoat

Sporting tradition from Oliver Brown in the form of fully-lined double-breasted tweed overcoat with gauntlet cuffs and flapped patch pockets. Picture yourself drinking a pint of stout in this coat. We're approaching some kind of telos, right?

Green Suede Loafer

You may have to put a request in with Cheaney to resurrect the Hubert loafer in green suede, but I was determined to put you in green top and tail. A lovely handmade pair of Northampton's finest. Have something in grain leather as backup in case the going gets extremely soft, if you get my drift.


  1. Sound sartorial advice as ever tweedy!
    Cant make Cheltenham,see you at Wincanton,april 17th.
    keep up the good work.

    1. Thanks Anon. Nice little course at Wincanton. Best wishes, Tweedy


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