Where to Shop: Kentucky Derby Weekend

Peacock Boutique

The city's purveyor of trend-conscious labels—Helmut Lang, Notte by Marchesa, Derek Lam, Missoni—is the place to go to graduate from the predictably fanciful Derby hat to statement-making "fascinator," the ornate head-piece made popular by Kate and Pippa Middleton. In the weeks leading up to the races, the shop carries Philip Treacy (a favorite of celebs and the royal family), and Katerina Miaoulis of Australian-based MemSahib Couture is in the store taking custom "fascinator" orders that start around $265. shopthepeacock.com

Elizabeth's Timeless Attire

Elizabeth Schaaf's prices are as retro as the Geoffrey Beene shifts and 1920s pearls in her shop—she has kept rates low since she opened 25 years ago. The dainty enclave feels like a time capsule with its collection of true vintage from the 1870s to 1970s and its Édith Piaf soundtrack. We walked out with a floor-sweeping jockey-printed dress ($79) and a 1960s wicker purse adorned with a race-track scene ($50). "All the old families make Louisville a great town for vintage," Elizabeth says. elizabethstimelessattire.com

Circe

A beauty bar carrying Paul & Joe Beaute powders, BECCA lip tints, and Tom Ford perfumes sets Circe apart. A makeup artist is on-site five days a week to translate beauty trends, and the shop's stock of DVF, Tracy Reese, and Tibi makes this a one-stop shop for head-to-toe Derby primping. shopcirce.com

Clodhoppers

A mainstay in women's wear since 1993, this shop made its mark carrying then-trendy Dr. Martens. Evolving its style with the times, it's now the place for a Derby sundress with one of the best selections in town of Milly, Trina Turk, and alice + olivia. Leading up to the Derby, it hosts eight trunk shows with swingy shifts and beaded necklaces from brands such as Elva Fields. clodhoppers.com

The Nitty Gritty

Peruse two floors of 1940s through 1960s-style dresses, hats, shoes, and accessories for playful Derby attire. Upstairs, grab costume three-piece suits and toppers for your guy. Or head to the kitchen section for the Derby party accessory: a vintage traveling bar with a shaker, stirrers, and a radio in a stylish suitcase ($20-$40; contents vary). nittygrittyvintage.com

Cellar Door Chocolates

Erika Chavez-Graziano's horseshoe-shaped chocolates and flavored bourbon balls make her the ideal chocolate sponsor for this year's Kentucky Derby Festival. Her limited-time collection of 16 bourbon balls are all variations of her original recipe. Pick them up at the original Butchertown Market spot, where you can spend the afternoon shopping at the other four retailers that share the space, such as Canoe and Work the Metal. cellardoorchocolates.com

Hillbilly Tea

Twenty-plus organic teas star at this farmhouse-hip eatery where tea pairings replace wine for special events. The food is Appalachian influenced with a healthful twist: Think Scotch eggs over kale for breakfast ($12) and palm-size duck burgers on focaccia ($10) for lunch. Everything is sourced from local farmers and served on Grandma's china. hillbillytea.com

Evolve

Men frequent this well-curated showroom for secondhand Prada sportcoats, Coach briefcases, and Brooks Brothers shirts at 60% off. "The Derby is the one time of the year where guys are willing to step outside their box, and they don't want to spend $1,500 for a suit they're going to wear only one time," says owner Gerry Mattingly. Send your guy here for J. Crew seersucker suits ($99), J. Press bow ties ($9), and Allen Edmonds leather shoes ($29). evolveconsignments.com

Scout

A modern aesthetic presides at this home-and-gift store where Hobo Bags are displayed on Mitchell Gold + Bob Williams cocktail tables. Since its 2004 opening, Scout has been an anchor in the East Market District's revitalization and a go-to for sleek sofas, local jewels, and fun gifts (such as cardboard versions of mounted trophy deer). Complete your Derby look with a colorful three-strand necklace from local designer W&M Custom Jewelry. scoutonmarket.com

The Crazy Daisy

This 20,000-square-foot antiques mall is where stylish shop owners go for furnishings and table-toppers to decorate their retail spots and homes. You'll find anything from mid-century chaises and Art Deco consoles to vintage train sets. Splurge on sterling silver mint julep cups, or get the race's annual glassware, a popular collectors' item for Derby fans since the 1940s. crazydaisyantiquemall.com

The Silver Dollar

This new saloon in an old firehouse on Frankfort Avenue is modeled after an Okie honky tonk, with a drink menu ruled by Kentucky whiskeys and Mexican tequilas and a record player cranking Merle Haggard and Buck Owens. The fried chicken livers ($8) and chicken and waffles ($17) are a good complement, but most people find it hard to leave the 42-foot bar, where the signature drink is An Old One & A Cold One: a shot of Old Grand-dad whiskey and Lonestar beer ($6). whiskeybythedrink.com