RELATED: Behind the scenes at the photo shoot »

MARC JACOBS dress, JEMMA WYNNE bangle, pendants, and chain, SHOUROUK bag, and JIMMY CHOO sandals

MARC JACOBS dress ($1,900), at Macy’s 28 Shop, 111 N. State St. JEMMA WYNNE bangle ($4,000), pendants ($8,650), and chain ($2,700), at Ikram, 873 N. Rush St. SHOUROUK bag ($905), at shourouk.fr. JIMMY CHOO sandals ($395), at Jimmy Choo, 63 E. Oak St.

 

 

THAKOON vest, ALTUZARRA pants, HERMÈS scarf, TED ROSSI bangles, and JIMMY CHOO shoes

THAKOON vest ($1,175), at Ikram. ALTUZARRA pants, collection available at Barneys New York, 15 E. Oak St. HERMÈS scarf ($375), at Hermès, 25 E. Oak St. TED ROSSI bangles ($64 to $118), at She Boutique, 483 Central Ave., Highland Park. JIMMY CHOO shoes ($595), at Jimmy Choo.

 

Photography: Sean Kennedy Santos; Producer: Gabrielle Fitzgerald; Stylist: Stacey Jones; Hair: Seiji/The Wall Group; Makeup: Katey Denno/The Wall Group; Model: Lena Ashikhmina/Supreme; Styling Assistant: Stephanie Soong; Shot on location at Hotel El Convento (elconvento.com) and the streets of San Juan, Puerto Rico

 

RELATED: Behind the scenes at the photo shoot »

ANDREW GN blouse and skirt, SARAH CHLOE ring, and JIMMY CHOO sandals

ANDREW GN blouse (about $3,960) and skirt (about $3,120), at Neapolitan, 715 Elm St., Winnetka, and Nordstrom, 55 E. Grand Ave. SARAH CHLOE ring ($298), at Valentina, 566 Chestnut St., Winnetka. JIMMY CHOO sandals ($395), at Jimmy Choo.

 

 

MAISON RABIH KAYROUZ gown and TED ROSSI bangles

MAISON RABIH KAYROUZ gown ($2,415), at Ikram. TED ROSSI bangles ($68 to $118), at She Boutique.

 

Photography: Sean Kennedy Santos; Producer: Gabrielle Fitzgerald; Stylist: Stacey Jones; Hair: Seiji/The Wall Group; Makeup: Katey Denno/The Wall Group; Model: Lena Ashikhmina/Supreme; Styling Assistant: Stephanie Soong; Shot on location at Hotel El Convento (elconvento.com) and the streets of San Juan, Puerto Rico

 

RELATED: Behind the scenes at the photo shoot »

SALVATORE FERRAGAMO top, shorts, and belt, and KORA cuffs

SALVATORE FERRAGAMO top ($1,490), shorts ($1,390), and belt ($275), at Neapolitan; sandals ($550), at Salvatore Ferragamo, 645 N. Michigan Ave. KORA cuffs ($90 to $240), at Tangerine, 1719 N. Damen Ave.

 

 

CHRIS BENZ blouse, TORY BURCH belt, DEREK LAM trousers, TED ROSSI bangles, SARAH CHLOE ring, HERMÈS bag, and ROBERT CLERGERIE shoes

CHRIS BENZ blouse ($795), at Chalk Boutique, 2611 Prairie Ave., Evanston. TORY BURCH belt ($175), at Tory Burch, 66 E. Walton St. DEREK LAM trousers ($550), at Neapolitan. TED ROSSI bangles ($64 to $118), at She Boutique. SARAH CHLOE ring ($198), at Valentina. HERMÈS bag ($2,700), at Hermès. ROBERT CLERGERIE shoes ($595), at selected Neiman Marcus stores.

 

Photography: Sean Kennedy Santos; Producer: Gabrielle Fitzgerald; Stylist: Stacey Jones; Hair: Seiji/The Wall Group; Makeup: Katey Denno/The Wall Group; Model: Lena Ashikhmina/Supreme; Styling Assistant: Stephanie Soong; Shot on location at Hotel El Convento (elconvento.com) and the streets of San Juan, Puerto Rico

 

RELATED: Behind the scenes at the photo shoot »

MARNI top and skirt, TED ROSSI bangles, and TORY BURCH espadrilles

MARNI top ($705) and skirt ($975), at Blake, 212 W. Chicago Ave. TED ROSSI bangles ($74 to $118), at She Boutique. TORY BURCH espadrilles ($175), at Tory Burch.

 

 

MAXMARA body suit, pants, and belt, TED ROSSI bangles, PACO RABANNE bag, and JIMMY CHOO heels

MAXMARA body suit ($525), pants ($1,050), and belt ($175), at MaxMara, 900 N. Michigan Ave. TED ROSSI bangles ($64 to $118), at She Boutique. PACO RABANNE bag ($1,650), at Ikram. JIMMY CHOO heels ($695), at Jimmy Choo.

 

Photography: Sean Kennedy Santos; Producer: Gabrielle Fitzgerald; Stylist: Stacey Jones; Hair: Seiji/The Wall Group; Makeup: Katey Denno/The Wall Group; Model: Lena Ashikhmina/Supreme; Styling Assistant: Stephanie Soong; Shot on location at Hotel El Convento (elconvento.com) and the streets of San Juan, Puerto Rico