Cheltenham (fashion) tips from a filly who knows her stuff

Lucy is a professional stylist from Bristol and avid racer goer, attending Cheltenham every year. Day to day not only is she a mother of two she  helps her clients create timeless looks by using Colour Analysis, Wardrobe Consultation and Personal Shopping. So I thought who better to ask for some tips on what (and not) to wear for The Cheltenham Festival…

So Lucy, you’re a regular at The Cheltenham Festival every year, for you what is a well dressed man at the races? What should a bloke be looking to wear?

The best dressed men are the dapper (usually older) winter racegoers. The regulars of the track seem to have the best style and know how to incorporate tweed into their outfit with a twist. Guys should look to them for inspiration and check out the parade ring and winners enclosure not just for a closer look of the horses but to see what the owners and trainers are wearing. Everyone makes more of an effort for the special meetings.

And where do you think a lot of guys go wrong? What are absolute horror shows in your eyes?

Fancy Dress! It’s funny for the first 5 mins on the train with your mates but then you are stuck looking like a twat all day. You also need to be mindful of the dress code of your enclosure.

Have you noticed any particular trends amongst what men wear to Cheltenham, and do you think it has changed over the years.

It’s usually a sea of grey blazers and dark jeans. I’ve definitely noticed guys making more of an effort which I applaud as the Festival is a special event.

What are your feelings on the “Peaky Blinders” look which I see a lot at courses and probably fall foul of myself!

The flat cap and three piece suit is good racing attire but it has become a bit of a uniform which is fine if you want to blend in but I like to see a man who is confident with his own style. I would love to see a bit more originality from the punters and adding some colour in your outfits.

And loafers with no socks, you see a lot of that. Yes or No?

I would say No for Cheltenham, it’s a cold day for bare ankles!

Any examples of stuff you might have seen in menswear departments that would be worth me considering wearing for the day?
There’s a lot of checks on the high street at the moment which would be an easy trend to wear to Winter races and an affordable way to update your race day look and wear beyond that into Spring too. My top tip would be to look at vintage and charity shops. It’s a more affordable way to get a class jacket that no-one else will have and you can get it tailored to fit you perfectly for less than you would pay on the high street meaning more betting spends! I found by chance my Ralph Lauren tweed jacket a week before Cheltenham Festival last year for a bargain price in St Peter’s Hospice charity shop. Of you’re looking for a new suit for the day you can’t go wrong with REISS or Ben Sherman are really making a come back with their classic mod look.
Cotton and Silk Blend Blazer from REISS
And for the ladies, do you think it is a bit of a cliche that they put a lot more effort and thought into their outfits or is it actually the case?

Going to the races is often just a once a year event for many women so of course they should see it as a special occasion and want to make an effort. It’s a fun outing so we want to look our best!

How do you tend to approach your outfit?

I’m ahead of the game for my clients but not much of a planner of my own outfit. I attend a few winter race meetings a year so I’ve got plenty in my wardrobe to choose from but the weather has a lot to do with what I eventually decide to wear. We’ve been pretty lucky in recent years and I’ve usually had a few from the Moet bar & Guinness Village to keep me warm but as I like to be where the action is I always layer up. For me it’s a great occasion to wear a hat so I visit Ani Stafford-Townsend of the Milliners’ Guild for inspiration and usually come up with an outfit around the hat. She has a great selection of men’s hats too and as I’ve got quite a big head I’ve donned some men’s’ trilbies and fedoras in the past too.

And again, what are the big dos and don’ts for girls.

Do think of the weather in March. I’ve seen girls freezing in mini skirts and bare legs so dress for the races in Winter and not your night out after.

Cheltenham is different to dressing up for Royal Ascot so unless you are trying to stand out to win a prize on Ladies Day stick to formal country attire like tweed, tailoring, knit dresses, leather trousers. I tell my clients to make a statement with their coat or outerwear as unless you are staying inside at a table or box your coat is what everyone will see or go for a plainer luxe coat and add interest with faux fur or feather accessories.

I always stick to comfy heels. To get the best from the races you want to be wandering about and getting where the action is so being on your feet for most of the day you need a chunky heel for comfort and to avoid sinking into the grass if the ground is soft.

Finally, the racing itself, what day are you going and do you have any particular fancies at this stage?

I’ve been going to Cheltenham Festival for years so have tried different days and different enclosures. You can’t beat the atmosphere of St Paddy’s Day on Thursday and I think Tatterstalls is the best value for a great day out. I’ve not planned my outfit yet let alone look at the horses but I had a few winners at Wincanton earlier this season I’ll be backing those jockeys and trainers again.

Thanks Lucy and enjoy the festival! To find out more about Lucy and the stylist services she offers visit her website and follow her on Instagram. 

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