Photograph by Jeff Elkins. Photograph of Kennedy by Art Rickerby/Getty Images.
1. Silky Smooth: Black Fleece silk dolman blouse and skirt, at Brooks Brothers, $650 and $550.
2. Hats Off: "Bruxelles" black felt hat with feathers, at Proper Topper (1350 Connecticut Ave., NW; 202-842-3055), $42.
3. Set in Stone: Fluorite earring by Gerard Yosca,at Sassanova (7134 Bethesda La., Bethesda; 301-654-7403), $105.
4. Go for the Gold: Bangle bracelet (top) by Asha by ADM, at the Shoe Hive; pavé link bracelet, at Ginger, $295 and $88.
5. A Tough Shell: "Nina" patent-leather clutch in tortoise shell by L.K. Bennett, at Bishop Boutique, $310.
6. On the Dot: "Jennifer" slingback pumps by Isaac Mizrahi, at Bishop Boutique, $140.
Photograph by Jeff Elkins. Photograph of Kennedy by George Elam/Alamy.
1. Cape Crusade: Luii houndstooth capelet, at the Lucky Knot,$169.
2. Sunny Skies: Prada sunglasses, at nordstrom.com, $290.
3. Black and White: "Kiera" clutch by Milly, at Bishop Boutique (815-B King St., Alexandria; 571-312-0042), $335.
4. Link Love: Hammered-link bracelet, at Ginger, $24.
5. Green Scene: Sleeveless organza damask jacquard top by Tibi, at Horse Boutique (1910 Towne Center Blvd., Annapolis; 410-626-9726), $298.
6. Pencil It In: "Smitty" skirt by Trina Turk, at Ginger (7114 Bethesda La., Bethesda; 301-664-9242), $228.
7. Need for Tweed: "Holly" tweed flats by L.K. Bennett, at Bishop Boutique, $275.
Photograph by Jeff Elkins. Photograph of Kennedy by Keystone Pressedienst/Zuma Press.
1. Into the Blue: Loren Hope earrings, at lorenhope.com, $48.
2. Pearl Two: Double-strand faux-pearl necklace, at the Lucky Knot (101 King St., Alexandria; 703-549-1797), $32.
3. Gloves Off: Leather gloves in palomino, at Talbots, $99.
4. Chic Shades: "Fairfax" sunglasses by Elizabeth and James, at the Shoe Hive (127 S. Fairfax St., Alexandria; 703-548-7105), $185.
Photograph by Jeff Elkins. Photograph of Kennedy by AP Images.
1. Lady in Red: "Gia" dress by Shoshanna, at Urban Chic (1626 Wisconsin Ave., NW; 202-338-5398), $350.
2. In the Shade: "Liv" sunglasses in greystone, at warbyparker.com, $95.
3. Something Blue: "Give It a Swirl" necklace by Kate Spade, at Sassanova, $98.
4. Arm Candy: Bangles with cabochon, at Bishop Boutique, $60 each.
5. White On: Loren Hope white-and-gold earrings, at Periwinkle (1557 Potomac Greens Dr., Alexandria; 703-519-5242), $48.
6. Seeing Spots: "Lauraly" pointed-toe calf-hair flats by Ivanka Trump, at Bishop Boutique, $130.
7. Keep It Brief: Quilted leather bag, at C. Wonder (Pentagon City; 703-413-7046), $248.
Photograph by Jeff Elkins. Photograph of Kennedy by Marka/Alamy.
1. Top It Off: "Ferris" hat by Genie by Eugenia Kim, at Wink (3109 M St., NW; 202-338-9465), $80.
2. Animal Attraction: Wool faux-leopard coat, at Ann Taylor, $278.
3. Aubergine Dream: Scoop-back dress by Contrarian New York Sade, at Zoe Boutique (130 S. Union St., Alexandria; 571-970-6324), $290.
4. Emerald Pretty: Diane von Furstenberg lizard-embossed envelope clutch, at the Shoe Hive, $195.
5. Shine On: Teatro Moderne bijou pyramid clip earrings by Alexis Bittar, at the Shoe Hive, $295.
6. Tiny Baubles: Faux-pearl-and-crystal stud necklace by R.J. Graziano, at the Shoe Hive, $55.
7. Pumped Up: "Pacey" stacked-heel pumps by Tory Burch, at the Shoe Hive, $295.
Photograph by Jeff Elkins. Photograph of Kennedy by John F. Kennedy Library/Zuma Press.
1. Check Mate: Peter Millar shirt, at the Lucky Knot Men's Store (103 King St., Alexandria; 703-549-1044), $115.
2. True Blue: Holebrook sweater, at the Lucky Knot Men's Store, $218.
3. Ship Shape: "Preston" sunglasses in whiskey tortoise, at warbyparker.com, $95.
4. Beat the Chill: Herringbone-and-stripe wool scarf, at Massimo Dutti (1220 Wisconsin Ave., NW; 202-944-8780), $69.50.
5. On Deck: "Cordones" sneakers by Toms, at the Lucky Knot Men's Store, $69.
6. Autumn Colors: Burnt-orange pleated-front chinos, at Brooks Brothers (3077 M St., NW; 202-298-8797), $99.
Photograph by Jeff Elkins. Photograph of Kennedys by Bettman/Corbis.
1. Well Suited: Milano sport coat and dress trousers, at Brooks Brothers, $750.
2. Fit to Be Tied: Navy tie with green dots by Collared Greens, at the Lucky Knot Men's Store, $85.
3. Pocket Flair: Rep slim tie, used as a pocket square, at Brooks Brothers, $80.
4. Cool and Crisp: Supima-cotton Ainsley French-cuff dress shirt, at Brooks Brothers, $92.
5. Buckle Up: Leather belt, at Suitsupply (2828 Pennsylvania Ave., NW; 202-800-7800), $59.
6. Head to Toe: Cotton dress socks, at Suitsupply, $16.50.
7. Oxford Blues: Peal & Co. medallion cap-toe shoes, at Brooks Brothers, $648.
This article appears in the November 2013 issue of Washingtonian.