How to dress warm and stylish at the Cheltenham Festival

There’s an art to looking smart and stylish without seeming like you’ve tried too hard. The Cheltenham Festival is the perfect occasion to show off how adept you are at styling sleek winter outfits that won’t leave you blue with cold.

There are a couple of points to remember. The first, according to Lady Alice Manners – a stylist and the daughter of the Duke of Rutland – is to steer clear of spindly heels or court shoes prone to sinking in the mud; the second is to avoid all things glossy. “You really don’t want anything too shiny or too perfect,” she says. “I love a fedora, for example, but it needs to be worn in. Some of the best-dressed women arrive in these tailored coats you can see they’ve owned for years. Personally, I think that looks much better than anything box-fresh.”

Of course, not everyone has a wardrobe filled with beautiful pieces on just the right side of worn, but Cheltenham is a great opportunity to build a stylish outfit from the coat up. Hence why the Royals – with their legions of occasion coats – are usually the stars of Cheltenham.

Jade Holland, founder of Holland Cooper says “Oh, it’s much more interesting than Ascot fashion-wise,”  “Cheltenham fashion is a fusion of fantastic cuts, great tailoring and heritage checks.

More than any other item, your coat is the showpiece of your outfit.

At this time of year, when most attendees are unlikely to take coats off during the day, it should be chosen with the same care that you might take when selecting a dress for Royal Ascot. The silhouette depends on your body shape and the style in which you feel most comfortable, but a caped style, or the kind of double-breasted, tailored coats favoured by the Duchess of Cambridge are always an elegant, timeless choice. Prints should be of the classic heritage variety – think prince-of-wales-check, tartan, or houndstooth. When it comes to colour, steer clear of black, which is a tad sombre for the occasion. Go for something bolder instead, like emerald green or true blue. If you’re more comfortable in neutrals, consider muted shades of brown, khaki, and you can’t go wrong with caramel. 

The Winter Occasion Dress

When we think of smart dresses, we tend to picture silk numbers or floral floaty pieces. Cheltenham, however, is a great opportunity to wear long-sleeved designs in thick velvet or fine knits that don’t usually get a starring role outside of Christmas. “If you’re in a box or are invited to a lunch, you’ll need a lovely dress or jumpsuit so don’t make the mistake of thinking it’s all about the coat, I love ankle-length knit dresses with a knee-high boot underneath.

The Not Too Formal Hat
Gillian Gilbourne wearing a stunning creation by Marc Millinery Marcmillinery

There isn’t a formal dress code for the Cheltenham Festival, so if you’re eager to wear something in a bold colour or with a sculptural brim, Ladies’ Day is the time to do it. There is a millinery middle ground though, which is celebratory, yet doesn’t look too try-hard, and that comes in the form of a felt beret – which both the Duchess of Cambridge and Zara Tindall have worn in previous years – I think a fedora or pillbox is a very chic option too.

If you need my help getting your wardrobe ready for spring and to face the world again, get in touch today to book your first personal Make Up Lessons and Private Consultations in Cork.

Leave a Comment

Your email address will not be published. Required fields are marked *