When it comes to Kentucky Derby style, the ultra-stylish Tootsies creative director, Fady Armanious, says it best: “The bigger the hat, the better.”

Once again, it’s time for little bit of sass, a lot of style, and, of course, two minutes of thrilling horse racing. Houstonians will be donning their best Southern genteel garb and elaborate, decorative hats — or fascinators — for the annual horse race and event held Saturday in May 1 at Churchill Downs in Louisville, Kentucky.

“Houstonians are ready to dress up and celebrate, especially after a tough year,” Armanious tells CultureMap.

When selecting an outfit for one of the hottest social events of spring, opt for a lighter color palette. Rarely are pant suits worn, sometimes jumpsuits, but mostly knee-length or longer dresses, Armanious shares. “You’ll see long-sleeve sheer, off the shoulder, and a lot of floral.”

Personal stylist and owner of Trending Style Houston, Elisabeth Webb, tells CultureMap that women can't go wrong with a crisp, voluminous, mid-length dress in Pantone's trendiest color. “The chicest Derby looks are the simplest," she notes. "Monochromatic is always a stand out look.”

Webb’s go-to brands for dressing the part, ranging from low to high, are STAUD, Alexis, Zimmermann, Johanna Ortiz, Texas-native Brandon Maxwell, and KHAITE.

For men, Armanious suggests lighter, more comfortable fabrics and colors. With the event being outdoors, keeping cool is a must in the Houston heat. “Linen is a go-to because it’s breathable,” he says.

“Stay away from darker hues like black and go for white or pastel tones,” Armanious advises. “Seersucker, pinstripes, and checkered suits are popular with men. If pastels aren’t for you, go for navy or khaki.”

Houston’s top restaurants and bars are hosting Kentucky Derby-themed parties with contests, live music, great food, and Derby-inspired style contests. May the best hat win!

Look to these 10 spots to celebrate the Kentucky Derby in style.

Hats, Hearts & Horseshoes
Where: Benefitting Bo’s Place, the annual event, previously hosted at the home of Paige and Tilman Fertitta, is at the Houston Polo Club this year. To purchase a table, visit this site. 4-6 pm, 8552 Memorial Dr.

Talk Derby To Me
Where: The Rustic is hosting an all-day affair, beginning with its Jam & Toast Brunch from 10 am-3 pm. Listen to live music by Remy Reilly and come dressed to impress for a chance to win in three best dressed contests.

The best-dressed couple, best-dressed male, and best-dressed female will each win a $100 gift card to The Rustic. Sip on Mint Juleps, made with Woodford Reserve Bourbon, and snack on Derby-inspired culinary features like Triple Crown Sliders, made with fried green tomatoes, hot chicken, and pulled pork. 1121 Uptown Park Blvd. and 1836 Polk St.

Keep your friends close and your mint juleps closer
Where: Alba Huerta’s Washington Avenue cocktail bar, Julep, reopens this Saturday, May 1 with a COVID-conscious version of their annual Derby Day Party. From noon-6 pm, guests can enjoy four satellite bars, two main bars, mint julep carts, a spirit-free cocktail bar, and the JulepToGo truck.

Expect BBQ and smoked oysters by Blood Brothers BBQ and Feges BBQ, boozy popsicles, a Topo Chico station, lawn games, a live DJ set, a T-shirt pop up by Vinyl Ranch, and of course, a live stream of the race. Tickets are available here. 1919 Washington Ave.

Run with the Romas
Where: Valobra Master Jewelers and Ferrari of Houston are hosting a pre-party from noon - 5 pm. Test drive the 2021 Ferrari Roma and watch the race in your Derby looks.

The latest ride share service, Alto, is transporting party-goers using Valobra’s promo code, which is good for $25 off. 2150 Westheimer Rd.

Patio Party
Where: BB Lemon’s Kentucky Derby patio party will feature DJ Mohawk Steve, a hat contest with prizes, Derby-inspired cocktails by Four Roses Bourbon, and more. Reservations are recommended. Call 713-554-1809 to book. 1809 Washington Ave., 2-6 pm.

Derby Day Party
Where: Swing by Chapman & Kirby’s celebration from noon-8 pm for live music, hookah, gift bags, and more. 2118 Lamar St., Suite 100

Off to the Races
Where: Backstreet Cafe is celebrating the crown jewel of horseracing with all-day drink specials featuring Maker’s Mark, an optional tasting menu with decadent food and cocktails, take-home julep kits, and prizes for the best hats.

The julep and snack kits are available Friday, April 30 and Saturday, May 1 for $60 and include six servings of Backstreet Cafe’s batched Maker’s Mark Mint Julep with fresh mint and crushed ice; two keepsake Julep cups and a Maker’s Mark insulated cooler bag; and bacon deviled eggs, grilled peach salad, and shrimp and pimento cheese grits.

For those dining in, enjoy the Maker’s Mark three-course brunch cocktail-paired menu for $45, available Saturday, May 1 from 10 am - 4 pm. Call 713-521-2239 for reservations. Maker’s Mark cocktail/flight specials are also available for $10, dine-in or to-go. 1103 S. Shepherd Dr.

Big Hat Weekend
Where: The all-day affair is taking place at Loch Bar in River Oaks District. The seafood tavern will come to life with a best hat contest and several bourbon-inspired cocktail specials, benefitting local nonprofit, Bo’s Place.

Spirits include a Maker’s Mark Flight with Maker’s Mark, Maker’s 46, Maker’s Loch Bar Private Select, and Maker’s Cask Strength ($22); Loch Bar’s rendition of a Mint Julep and a Maker’s Gold Rush cocktail with an edible gold leaf. The eatery will also offer Kentucky Hot Brown Sliders served open face ($16). 4444 Westheimer Rd., Unit G110

Let the Race Begin
Where: From noon-7 pm, William Price Distilling Co. is hosting its inaugural Derby Party featuring DJ Matthew Dunn. Enjoy the cocktail lounge and bites from Zach Cooks BBQ. Tickets are available here. 970 Wakefield Dr.

Gettin’ Down and Derby
Where: Houston’s whiskey destination, Permission Whiskey, is joining forces with Maker’s Mark this Derby Day. Expect a mobile bar, Maker’s Mark glass dipping station, and style prizes with local judge Danielle Dubois, also known as Hangry Houstonian. For reservations, direct message Permission Whiskey on Instagram.

Megan Cushing and Caroline Walter donned their Southern best.

Photo by Daniel Ortiz

Megan Cushing and Caroline Walter donned their Southern best.