Skip links


What men wear to the Cheltenham races enclosures

The Cheltenham Gold cup races is one of the Premier horse racing events of the year, also well known for its more trendy dress code, so it’s really the time for you Gents to let your style shine. I’m always encouraging Men to be much more experimental with their clothing and events like these are such a great time to just go for it with wild abandon and with no fear of judgement.

Officially, unlike  Ascot there is no strict dress code for Men apart from an absolute no to jeans. However, within enclosures, smart attire must be worn. With the event taking place in March, the weather can very much dictate what you wear on the day, so you may like to consider a few options for last minute weather changes.

Fancy dress is a no no if you’re within the enclosure but you will see some life size leprechauns walking about outside of the enclosures, but we know our super stylish customers won’t be adoring giant, green costumes and will be suitably stylish.

Over the years, Men have been trading the classic suit for a more country inspired look. Think tweeds in plain or bold checks, brushed cotton shirts and cravats for those wishing to go all out.The show peaky blinders has been a huge source of inspiration to Cheltenham goers for the past couple of years, with flat caps and baker boy caps, three piece suits with peak lapels. If you love a tweed suit, now is the time to go for it! You really can go all out, there’s really no limit, particularly if its a chilly March day.

Here are some ideas for inspiration for you:


Tweeds have really got more exciting over the years, with bolder checks, wilder colours and lighter weights, so if you like to layer but fear being absolutely boiled, lightweight lambswools are a really great choice.


Going to Cheltenham means you can wear something out of the norm. If you’ve always wanted to dress like a country gent, this is the few days where its formally accepted. So whether you go for ready to wear or made to measure, let your imagination run wild. Just always make sure that everything fits beautifully.

Choose chunky tweeds for sports jackets and heavier twills, cottons, moleskins for your trousers.


As the weather tends to be unpredictable at the time Cheltenham comes around, you may be wise to prepare your outerwear and at AW, we love an overcoat. Classic Crombies and Chesterfields are the norm. Why not have one made and choose your own fabulous colour and contrast collar. An overcoat always helps  to keep your look in line with the Cheltenham feel, all whilst staying suitably warm.


Whether you’re opting for a classic look or a more country feel, always add a clashing tie and pocket square to create a more trendy look. You want to look like you’ve tried but not tried too hard by being all matchy matchy!


Let’s not let the final element of your look down with poor footwear. Choose a pair of chocolate brown, Chelsea boots if opting for a sports jacket/twill trouser combination. Alternatively, why not choose some brogues to match that classic gent look? If you’re wearing tweed and earthy colours (Think brown, beige etc..) opt for brown footwear. If you’ve decided upon wearing more of a classic suit choose black for a more formal look.

Here’s our quick,  go to list:

  • Tweed jackets
  • Twill trousers
  • Tweed three piece suits
  • Brushed cotton shirts
  • Flat caps
  • Contrast waistcoat
  • Wool or silk tie in warm colours
  • Take a Brolly (for the rain or for style, we don’t care!)


We have some great options in store or if you’re in time, made to measure to really set heads turning. Contact us here if you’re needing a little extra guidance.

View more case studies…

Need some style inspiration?




Made to Measure

Free Guide

Retirement Advice?


Download your free eBook with advice from our experts.