We love an excuse to wear a hat and the races are particularly fun: there are no brides to accidentally upstage and you can be as daring as you like, particularly on Ladies’ Day.
The headpieces on this list should cover all the bases. Most are by independent milliners, with a couple of high-street options in the mix.
Not sure what shape will suit? Then try these simple tricks. If you have a long face, balance out length by wearing a hat that sits to the side, while wide-shaped faces should avoid anything too narrow. A squarer face shape is often softened by rounded styles or veils, and asymmetric shapes tend to suit everything.
If you’re off to Royal Ascot and are in the Royal Enclosure make sure your hat meets the dress code. There, any headpieces must have a solid base of at least 10cm and fascinators are a no-go.
Also, be sure to check how long your hat will take to arrive before your buy as bespoke pieces can take a few weeks and milliners are particular busy in the summer season.
1. Rachel Black La Boo Disc: £285, Rachel Black Millinery
The elaborate bow atop this by north London milliner Rachel Black elevates the classic disc into Ladies’ Day-worthy territory. At 28cm, it will work for the Royal Enclosure and comes in this versatile ivory or teal. It’s secured with a wire headband, which you can get to match your hair colour.
2. Philip Treacy, Pillbox Embellished Veiled Headpiece: £1,485, Net-a-Porter
One of Britain’s best known milliners, Philip Treacy’s creations have adorned the heads of royalty and A-Listers alike (yes, he was the man behind Princes Beatrice’s “pretzel” hat at the Duke and Duchess of Cambridge’s wedding). Elegant but eye-catching, this pillbox hat is perhaps one of his most wearable designs and will be useful way beyond the race course. On an ivory glazed paper base, there’s a bouquet of faux flowers in pretty blue, pink and yellow pastels, amped up by a sculptural scroll with black patent leather running down the middle. The veil adds to the dramatic feel and the slim velvet band means it fits securely without pinching. Yes, this one is expensive, but you’re investing in your own piece of British millinery history.
3. Rosie Olivia Millinery Basilica: £425, Rosie Olivia Millinery
Don’t do florals? Then this red felt design by Brit milliner Rosie Olivia could be the one for you. Rosie trained under Philip Treacy and Stephen Jones and like their pieces, hers make an impact. The twisted bow in phone box red makes for a dramatic but wearable look. It’s designed to be worn on the left side of your head and is secured with clear elastic. If red doesn’t work with your race-day outfit, it can be made in other colours.
4. Emily London, Richmond Couture Pillbox Hat: £665, Harvey Nichols
Hats are really works of art and this ready-to-wear number by British designer Emily Baxendale is a case in point. The chartreuse and hot pink silk loops give it height and add drama but it’s really wearable. The hat is designed to sit to the right side of the head at an angle, a style that will suit most face shapes. There’s a fine wire headband and hidden elastic, making it feel secure if you get a little too enthusiastic cheering on your steed.
5. Marell Kull Maiko Straw Boater: £345, Marell Kull
London-based Estonian model Marell Kull has been training as a milliner in-between shoots. We love the classic-with-an-edge vibe of her hats. Think discs, buttons and boaters with leather detailing. This two-tone straw boater with hand-crafted leather roses and band is a toughend-up take on florals and ribbons. It’s held on with a headband. It’s made to order and takes two-three weeks and can be made in other colours on request.
6. Awon Golding, Modern Boater with Ombre Crinoline Trim: £445, Love Hats
What better way to style-out the races than with a hat that celebrates the British summer? By award-winning London-based milliner Awon Golding, this is a playful take on a straw boater. We love the lavender pompom on both sides of the brim that conjures up flowers in full bloom, and the two little beaded bumblebees that make this one a conversation starter for sure. The crown is 10cm and the brim measures 26cm, so this is one that would pass muster in the Royal enclosure.
7. Laura Apsit Livens Bay Straw Beret: £720, Laura Apsit Livens
From Paloma Faith to Princess Beatrice, Laura Apsit Livens’ designs have adorned some very well-known heads – and her pieces feel super-modern yet always elegant. This cornflower blue and golden yellow combination from her latest collection is very striking and easier to pull off, for us at least, than some of her boater and trilby styles. The straw beret’s kept on with a slim band that you can choose to match your hair colour. As it’s made to order, make sure you allow up to two weeks for delivery.
8. Clare Faux Pearl Down Brim Disc Hat: £95, John Lewis
For something a bit more understated, this from the high street is a good choice. The ivory hue and round crown promise to compliment most outfits while the addition of iridescent pearls and two quills give it a little oomph. We’d style this with a sleek up-do or chic loose waves.
9. Sahar Millinery Straw Red Button Fascinator: £280, Sahar Millinery
If you like the look of a button-style hat but want height, try this by London milliner Sahar Freemantle. the base and abstract flower in the same straw gives this one a contemporary but very wearable look. It’s held on with elastic and can be made in other colours if this doesn’t work. Her latest collection also includes a very of-the-moment cherry blossom creation from the latest collection.
10. Clea Broad Anna Headband: £115, Clea Broad
Not a hat person? Then try a floral headpiece. As a trained costume designer and milliner, Broad’s piece are gloriously theatrical and we think a bit of flower power will also go down well at the races. The Anna features yellow peonies and purple hydrangeas on a pretty ivory silk and gold lace-covered headband. At 4cm thick at it’s widest point, the band feels very secure. Clea can also create bespoke pieces to order.
The Verdict: Hats for the races
For an easy-to-wear style by an independent designer that will work way beyond race day, try Rachel Black’s versatile La Boo Disk. If you’re looking for something a little more playful, we love Awon Golding’s bumblebee creation. And where budget permits, we recommend investing in Philip Treacy’s Pillbox design for your own little piece of millinery history.
IndyBest product reviews are unbiased, independent advice you can trust. On some occasions, we earn revenue if you click the links and buy the products, but we never allow this to bias our coverage. The reviews are compiled through a mix of expert opinion and real-world testing.