My favorite Audrey Hepburn movie—and one of my favorite films overall—is My Fair Lady (1964). It was the fashion that drew me in and one of the film’s most fashionable scenes is the one at Ascot Racecourse, where Eliza Doolittle (Hepburn) dons a fabulous white gown and enormous hat while taking in the action.

After we moved to London, I immediately added Royal Ascot to my list of events I had to experience at least once. It’s a nearly weeklong race meeting full of pomp, glamour and people-watching. One of the biggest days is the third, which is commonly referred to as Ladies’ Day. It’s a day to show up and show out, so my friend and I decided to take in all the splendor from the Queen Anne Enclosure.

For this week’s edition, I decided to do something different. I thought I’d share more about what I wore to Ascot, because while it’s certainly an expensive day out, you don’t have to spend a fortune to create a memorable race day look.

Plus I’m already dreaming up what to wear next year …

1. Bowe Millinery Handmade Headpieces (£85 and up)

While my wardrobe is typically very heavy on neutrals like black, Ascot is all about color. I loved the golden yellow shade and statement-making shoulders of this dress from Anthropologie, which is now sadly sold out. Shopping for a hat was new territory for this American, so I went to Etsy and that’s where I found Anne-Marie Bowe, an Irish milliner based in Camberley, England. Her headpieces are chic and modern, with eye-catching sculptural details and vibrant colors. She matched my headband to my hair and that, plus the attached comb kept my hat (similar here) perfectly in place.

2. Pat McGrath MTHRSHP Velvet Liaison Palette (£64)

Wearing such bold colors, I wanted to keep my makeup look minimal and fresh. I originally snapped up this all-matte eye palette by legendary makeup artist Pat McGrath because I was looking for a dusty purple shade (and I had a coupon), but every hue is perfection. Her shadows are versatile and give great color payout. I used the bottom beige shade on my entire lid and the dark brown along my top and bottom lashes, creating a smokey look that made my eyes stand out under that big hat without being too dark for daytime. No matter how slick my skin got, nothing budged.

Another MIDDI pick I used to create this look was this amazing drugstore concealer.

3. Naturalizer Joy Dress Sandal (£130)

Ascot is a long day. Gates open at 10:30 am, the last race is at 6 pm and the official close is 8 pm. It’s also a lot of running around if you want to make bets, try different foods and catch the trophy ceremonies. I avoid removing my shoes at all costs, so I had to do the impossible: Find a comfortable pair of heels. Naturalizer’s shoes have come a long way since I last saw them in a mall. This pair has a classic style with a 3 3/4" block heel, 3/4" platform, wide front strap and a well-padded insole. This was my first time wearing them and I made it all day without any limping or blisters.

My other accessories included a floral Furla shoulder bag previously featured in this edition and a snake brooch I found in this Etsy shop.

How to make … a Pimm’s Cup

The unofficial drink of summer here in the UK is the Pimm’s Cup. Pimm’s is a gin-based liqueur that is most often mixed with lemonade or ginger ale. To make a classic, refreshing Pimm’s Cup, here’s what you’ll need, courtesy of BBC Good Food:

• 200 ml Pimm's No. 1

• 600 ml lemonade

• Sprigs of fresh mint

• Sliced cucumber, orange and strawberries

Fill a large jug with ice, then add the Pimm’s and lemonade and stir to combine. Mix in the mint, cucumber, orange and strawberries and serve. It’s impossible to mess up.

Last week on MIDDI …

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