1. Seaweed and Stone Create a Soulful Setting
—and a subtle palette. According to our roving fashion editors, the temperature drops at night even in Cape Town, South Africa, where this story was shot, so a thin cotton and linen hoodie and linen and silk mesh tank (Eileen Fisher, $109 and $158) are indispensable. We love mixing a romantic satin organza skirt (Vera Wang, $975) with a streetwise top.
2. Try speaking Trench
—in a sleeveless navy dress (Teri Jon, $295), you'll never look less than smashing. A handsome tricolored tote (Yves Saint Laurent) can handle any buying spree, including the one-of-a-kind beaded crafts made by disadvantaged Cape Town women for Monkeybiz, a vibrant nonprofit shop (Mathapelo Ngaka, right, is one of the owners). Earrings, By Boe. Beaded necklace, Shirley Fintz for Monkeybiz. Link necklace, O Oscar. Shoes, Marc by Marc Jacobs.
3. Who Needs Dinner
...when there's high tea? British traditions and a brilliant jacquard shift (Piazza Sempione, $965) make for a sophisticated afternoon. The opulent Victorian setting of Cape Town's gracious Table Bay Hotel—marble fireplaces, gilt mirrors, old-school ship paintings—demands a dress; like this one, shaped enough to be stylish but sufficiently loose to permit an extra cream puff. Earrings, By Boe. Bracelet, O Oscar. Sandals, Anya Hindmarch.
4. A Place in the Sun
A plate of warm scones and a flirty yellow dress (J.Crew, $265), are a fine way to begin a visit to one of South Africa's oldest wine farms. Then we added vivid touches like a red cardigan (Gap, $40), coral-colored choker (Roxanne Assoulin for Lee Angel), and green patent leather heels (D&G). Because the colors are of equal intensity, the combo doesn't look as if you had one vintage too many. Photographed at the Jonkershuis Restaurant at the Groot Constantia Wine Estate.
5. Cosmopolitan Buzz
Lawn-partying at the 17th-century Castle of Good Hope, the nation's oldest building. Blouse, O Oscar, $99. Pants, Tevrow+Chase, $195. Sunglasses, Valentino. Shoes, Marc by Marc Jacobs.
6. Out for a Drink
Chef Bruce Robertson at his hip Showroom Restaurant. Dress, Rebecca Taylor, $320. Cashmere cardigan, Ralph Lauren Black Label, $598. Earrings, Melinda Maria. Cuff, Kara by Kara Ross. Belt, Pelle Melle.
7. Flowy Slacks for a Day on the Water
Zipping around the waterfront in an Adrenalin speedboat. Tee, Three Dots, $88. Pants, Nicole Miller, $235. Sunglasses, Valentino. Bracelet, O Oscar. Sandals, Lambertson Truex.
8. Natural Beauty
Scenic viewing courtesy of the Table Mountain Cableway. Left: Blazer, Philosophy di Alberta Ferretti, $915. Shirt, Gap, $45. Pants, Vince, $220. Ring, Ippolita. Bracelet, Roxanne Assoulin for Lee Angel. Thongs, Christian Louboutin. Right: Cardigan and polo shirt, Tory Burch, $235 and $150. Skirt, Ann Taylor, $98. Bracelet, Roxanne Assoulin for Lee Angel. Flats, Belle by Sigerson Morrison.
9. On the Move in Dressed-Up Denim
Dress up your denim with white jeans rather than blue (Lacoste, $140). Pink and red stripes (tee, Charles Nolan, $188) make a classic navy blazer pop (Rag & Bone, $550). Straw hat bought locally. Watch, Fossil. Belt, Pelle Melle.
10. See the Sights in a Flattering Shape
This dusty rose dress (Derercuny, $850) is so alluring, you need a naval escort just to go shopping—maybe for unusual edibles at Gogo's delicatessen in Simon's Town. Earrings, Julie Sandlau. Belt, Nine West. Bag, Hollywould. Sandals, Stuart Weitzman.
11. Skirts that Move
A rose-print A-line (Liz Claiborne, $128) and poplin top (GinnyH by Ginny Hilfiger, $250) are great for tasting the grapes at Groot Constantia Wine Estate. Belt, Kristin Kahle. Bangles, Roxanne Assoulin for Lee Angel. Shoes, Sigerson Morrison.
12. Bold and Bright for a Leisurely Walk
A swingy 1950's-style skirt (Marni, $1,260) looks surprisingly sporty when matched with a laid-back polo (L.A.M.B., $245). Citrus-colored flats (Belle by Sigerson Morrison)—a smart choice for long, exploratory walks—complement the feel-good mood of the top's bold stripes. Sunglasses, Tommy Bahama. Straw bag bought locally.
13. Take the Preppiness Out of a Twinset
Unmatched (but color-compatible) silk knits (Pringle of Scotland, $950 and $750) are terrific with slim Bermuda shorts (Pollini, $335). To look the part in a foreign place, pick up native products (like this Panama hat) and make friends with locals (like the neighborhood kids at the colorful cabanas on St. James beach). Earrings, Laura J Designs. International flights courtesy of South African Airways.