And two people who have spent a lot of time thinking about how to dress for that outdoor event, which will be May 3, are race director Jill Abbott of Centreville, and her daughter, Mikki, who at the age of 13 is a lifelong attendee.
Jill's tips for picking an outfit for the event, which can be hot or cold, dry or rainy, or some of all of that in one day, include wearing hats, sunglasses and sunblock. She says she's seen a lot of Monday morning raccoon eyes from people who forgot their sunblock, or forgot to re-apply during the day.
She also recommends that people think about their footwear. Sandals are a great choice for many, but she doesn't like to wear flats and always has some kind of heel. However, heels can play havoc with the grass at Winterthur and be treacherous to walk in unless you choose the right kind of chunky heel or wedge.
She recommends women consider equestrian tailgate chic and wear riding or hunter boots with dresses and hats. They also may want to consider bringing a light sweater or wrap, as well as a wristlet to carry ID and a cell phone.
She suggests men consider wearing khakis with polo shirts or button-down shirts. Tie one on with a bow tie, she says. Plaids are always great, she says.
Here's a look at how Jill and Mikki will dress, and what they think about fashion every day.
Her style
Jill: "I have always dressed conservatively, tailored and a little preppy. My mother worked at Talbots for 25 years and she knows what looks nice so I let her style me. Those styles also fit my body type and petite build at 5-foot-3."
Mikki: Preppy chic.
Wearing, at the stable of Duncan and Beatrice Patterson in Rockland
Jill's first outfit: Trina Turk navy blue paisley dress from Ellie in Greenville; hot pink Point-to-Point color wide-brim hat from That's Hats in Chadds Ford; Talbots tan mid-calf western boots; accessories from Wilmington Country Store in Greenville.
Mikki's first outfit: Lilly Pulitzer magenta lace dress from Wilmington Country Store in Greenville; Lucky Brand gold ballet flats; white "Kardashian" mid-brim hat from That's Hats Accessories Boutique in Chadds Ford.
Jill's second outfit: Trina Turk multicolor dress from Ellie; Helen Kaminski Villa6 Point-to-Point hat, open-toe wedge sandals by Coclico.
Mikki's second outfit: 4Collective pink dress from entreDonovan in Wilmington; tan fascinator from That's Hats in Chadds Ford; Vince Camuto copper St. Tropez sandals.
Jill's third outfit: Hot pink jacquard dress from J McLaughlin in Greenville; black small-brim hat from That's Hats; Vaneli chunky tan leather sandals from entreDonovan in Wilmington.
Mikki's third outfit: Lilly Pulitzer turquoise dress from Wilmington Country Store; Vince Camuto sandals; white organza hat with turquoise flower accent from That's' Hats.
Where she shops
Jill: She enjoys shopping at local boutiques, including Peter Kate, Ellie, Wilmington Country Store and J. McLaughlin in Greenville. Online, she's fan of Rue La La.
Mikki: Pink by Victoria's Secret, Abercrombie and Fitch, Hollister.
Fashion icon
Jill: Diane Von Furstenberg.
Mikki: Lilly Pulitzer, whose colorful, springy, ladylike designs are ideal for Point-to-Point.
Favorite designer:
Jill: Trina Turk, Diane von Furstenberg, Nicole Miller, JBrand and AG Jeans.
Mikki: Lilly Pulitzer. Who else?
Indispensable wardrobe item:
Jill: Her suede jacket by Ecru.
Mikki: She finds herself reaching again and again for her grey Ralph Lauren polo shirt.
Most recent purchase
Jill: The Helen Kaminsi Villa6 hat she will wear for both Point-to-Point and to the beach this summer.
Mikki: Vineyard Vines pullover.
Oldest item in her closet
Jill: Overcoats. "Not a big fan of purchasing those."
Best foot forward
Jill: "If I could wear boots year round I would. All colors, heels, styles and heights." Her favorite brands are Aquatalia and Paul Green.
Mikki: Her footwear faves are Trina Turk flip flops, Tory Burch flip flops, Hunter boots and UGG boots.
Favorite color
Jill: Red and blue.
Mikki: Pink.
Favorite fragrance
Jill: She has two, Dolce Gabbana Light Blue and Clinque Happy.
Mikki: Warm and Cozy by Victoria's Secret.
Go-to outfit on a saturday night
Mikki: Leggings and a polo shirt.
Go-to outfit
Jill: "I am a dress girl, any dress in my closet. I wear them every day. I prefer dresses made from wash-and-wear stretchy material like J McLaughlin, Nicole Miller and Trina Turk. These dresses are comfortable, don't wrinkle, keep their shape and always look good."
The great pantyhose debate
Jill: "No debate, no hose. Instead, I use Neutrogena Sunless Tanning Spray year-round."
Mikki: "I'm against pantyhose."
Fashion inspiration
Jill: Diane Von Furstenberg.
Mikki: "My mom."
Ace accessory
Jill: "Sunglasses, wear them all the time, usually on the top of my head keeping my hair back."
Mikki: "My monogram necklace."
Worth the splurge
Jill: Daily facial cleaning regime and good moisturizer. "I use Roden & Fields. I am also a fan of Natura Bisse sheer moisturizer on days I need extra coverage or spot attention."
Mane, makeup and manicure
Jill: For hair, Lorrie Doyle of Currie, Hair and Nails West Chester; she buys her makeup at Houpette in Greenville. She relies on Polished Salon in Trolley Square for her manicure.
Mikki: "For my hair, I go to Brian at Sherif Zaki" in Greenville. Like her mom, she has her nails done at Polished Salon.
Skirts or pants?
Jill: Skirts.
Mikki: Skirts.
Flats or heels?
Jill: "Heels always, I don't wear flats, I'm too short."
Mikki: Flats.
Diamonds or pearls?
Jill: Diamonds.
Mikki: Pearls.
Why fashion is important
Jill: "It is your image to the rest of the world. People make first impressions and remember you by what you wear and how you present yourself publicly. It's important to dress well and feel good about yourself."
Mikki: "Fashion is important to me because it's a great way to express yourself and show off all the great things about yourself. You can express yourself with all kinds of different clothes. I think that fashion – the clothes, jewelry, and shoes you choose – is a great way for people to get to know you."
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