PETER PILOTTO dress, K.AMATO necklace, DAVID YURMAN rings and bracelets, JIMMY CHOO bag, and NICHOLAS KIRKWOOD shoes

PETER PILOTTO dress ($1,870), at Neapolitan Collection, 715 Elm St., Winnetka. K.AMATO necklace ($74), at Tribeca Boutique, 1035 W. Madison St. DAVID YURMAN rings ($2,450–$6,300 each) and bracelets ($725–$12,500 each), at David Yurman, 40 E. Oak St. JIMMY CHOO bag ($2,150), at Jimmy Choo, 63 E. Oak St. NICHOLAS KIRKWOOD shoes ($875), collection available at Saks Fifth Avenue, 700 N. Michigan Ave.

 

Photograph: David Leslie Anthony; Stylist: Stacey Jones; Hair and Makeup: Angie Barton/Ford Beauty; Model: Simone Kerr/Ford Chicago; Styling Assistant: Stephanie Soong; shot on location in St. Lucia at Calabash Cove (calabashcove.com)

 

JASON WU dress, MAXMARA necklace, K.AMATO cuffs, MIRIAM HASKELL flower cuff, and NICHOLAS KIRKWOOD shoes

JASON WU dress ($1,995), at Ikram, 15 E. Huron St., and selected Neiman Marcus stores. MAXMARA necklace ($450), at MaxMara, 900 N. Michigan Ave. K.AMATO cuffs ($48 each), at k-amato.com. MIRIAM HASKELL flower cuff ($550), at Space519, 900 N. Michigan Ave. NICHOLAS KIRKWOOD shoes ($875), collection available at Saks Fifth Avenue.

 

Photograph: David Leslie Anthony; Stylist: Stacey Jones; Hair and Makeup: Angie Barton/Ford Beauty; Model: Simone Kerr/Ford Chicago; Styling Assistant: Stephanie Soong; shot on location in St. Lucia at Calabash Cove (calabashcove.com)

 

DIOR blouse, DIOR shorts, TORY BURCH jacket, ALEXIS BITTAR ring, MAXMARA bracelets and bag, and JIMMY CHOO shoes

DIOR blouse ($3,800), at Saks Fifth Avenue, 700 N. Michigan Ave. DIOR shorts ($1,400), similar styles at Neapolitan Collection. TORY BURCH jacket ($525), at Tory Burch, 45 E. Oak St. ALEXIS BITTAR ring ($355), at Alexis Bittar, 1710 N. Damen Ave. MAXMARA bracelets ($325 each) and bag ($1,095), at MaxMara. JIMMY CHOO shoes ($795), at Jimmy Choo.

 

Photograph: David Leslie Anthony; Stylist: Stacey Jones; Hair and Makeup: Angie Barton/Ford Beauty; Model: Simone Kerr/Ford Chicago; Styling Assistant: Stephanie Soong; shot on location in St. Lucia at Calabash Cove (calabashcove.com)

 

GUCCI blouse, RACHEL ROY suit, TRIBUNE STANDARD earrings and LOUIS VUITTON shoes

GUCCI blouse ($1,700), at Gucci, 900 N. Michigan Ave. RACHEL ROY suit (price on request), collection available at Neiman Marcus, 737 N. Michigan Ave. TRIBUNE STANDARD earrings ($150), at Ikram. LOUIS VUITTON shoes ($1,350), at Louis Vuitton, 919 N. Michigan Ave.

 

Photograph: David Leslie Anthony; Stylist: Stacey Jones; Hair and Makeup: Angie Barton/Ford Beauty; Model: Simone Kerr/Ford Chicago; Styling Assistant: Stephanie Soong; shot on location in St. Lucia at Calabash Cove (calabashcove.com)

 

TRIBUNE STANDARD dress, KENDRA SCOTT cuffs, and MULBERRY bag

TRIBUNE STANDARD dress ($650), at Ikram. KENDRA SCOTT cuffs ($145 each), similar styles at Nordstrom, 55 E. Grand Ave. MULBERRY bag ($1,100), similar styles available at Intermix, 1633 N. Damen Ave.

 

Photograph: David Leslie Anthony; Stylist: Stacey Jones; Hair and Makeup: Angie Barton/Ford Beauty; Model: Simone Kerr/Ford Chicago; Styling Assistant: Stephanie Soong; shot on location in St. Lucia at Calabash Cove (calabashcove.com)