Martin Grant jacket, bustier, jodhpurs, Lana Jewelry Sunrise hoops, Kara Ross square bangles, and Marni sandals

MARTIN GRANT jacket ($1,827), bustier ($740), and jodhpurs ($1,390), at Chalk Boutique, 2611 Prairie Avenue, Evanston; and Barneys New York, 15 East Oak Street. LANA JEWELRY Sunrise hoops ($856), at lanajewelry.com. KARA ROSS square bangles ($175 each), similar styles at Frances Heffernan, 810 Elm Street, Winnetka. MARNI sandals ($825), at Blake, 212 West Chicago Avenue; and Barneys New York.

 

Photograph: Brian Doben

Producer: Nancy Corbett
Stylist: Stacey Jones
Hair & Makeup: Cindy Adams/artists by Timothy Priano
Model: Edda Petursdottir/Supreme
Photography Assistant: Jesper Justesen
Styling Assistant: Stephanie Soong
SHOT ON LOCATION AT Paradisus Palma Real Resort, Punta Cana, Dominican Republic, paradisus.com.

 

Michael Kors asymmetric zipper shift dress and sandals

MICHAEL KORS asymmetric zipper shift dress ($2,995) and sandals ($685), all at Michael Kors, 900 North Michigan Avenue.

 

Photograph: Brian Doben

Producer: Nancy Corbett
Stylist: Stacey Jones
Hair & Makeup: Cindy Adams/artists by Timothy Priano
Model: Edda Petursdottir/Supreme
Photography Assistant: Jesper Justesen
Styling Assistant: Stephanie Soong
SHOT ON LOCATION AT Paradisus Palma Real Resort, Punta Cana, Dominican Republic, paradisus.com.

 

Lana Jewelry Sunrise hoops, Thakoon Armor dress, Adidas Candy watch

LANA JEWELRY Sunrise hoops. THAKOON Armor dress ($1,890), at Ikram, 873 North Rush Street. ADIDAS Candy watch ($60), at Macy’s, 111 North State Street and other locations.

 

Photograph: Brian Doben

Producer: Nancy Corbett
Stylist: Stacey Jones
Hair & Makeup: Cindy Adams/artists by Timothy Priano
Model: Edda Petursdottir/Supreme
Photography Assistant: Jesper Justesen
Styling Assistant: Stephanie Soong
SHOT ON LOCATION AT Paradisus Palma Real Resort, Punta Cana, Dominican Republic, paradisus.com.

 
Lana Jewelry Sunrise hoops, Adidas Wooster watch, Narciso Rodriguez dress

LANA JEWELRY Sunrise hoops. ADIDAS Wooster watch ($60), at Macy’s. NARCISO RODRIGUEZ dress ($1,750), at Ikram; Chalk Boutique; and Barneys New York.

 

Photograph: Brian Doben

Producer: Nancy Corbett
Stylist: Stacey Jones
Hair & Makeup: Cindy Adams/artists by Timothy Priano
Model: Edda Petursdottir/Supreme
Photography Assistant: Jesper Justesen
Styling Assistant: Stephanie Soong
SHOT ON LOCATION AT Paradisus Palma Real Resort, Punta Cana, Dominican Republic, paradisus.com.

 

Prada button-down top with veiled back, at Prada, open-back top and briefs, Loro Piana Eloee wedges, Lana Jewelry Sunrise hoops

PRADA button-down top with veiled back ($670), at Prada, 30 East Oak Street; open-back top ($1,360) and briefs ($260), similar styles available at Prada. LORO PIANA Eloee wedges ($1,295), at Loro Piana, 45 East Oak Street. LANA JEWELRY Sunrise hoops.

 

Photograph: Brian Doben

Producer: Nancy Corbett
Stylist: Stacey Jones
Hair & Makeup: Cindy Adams/artists by Timothy Priano
Model: Edda Petursdottir/Supreme
Photography Assistant: Jesper Justesen
Styling Assistant: Stephanie Soong
SHOT ON LOCATION AT Paradisus Palma Real Resort, Punta Cana, Dominican Republic, paradisus.com.

 

DKNY blazer, Lacoste cardigan, IZOD polo shirt, Marni striped pants, Maria Sharapova by Cole Haan Air Gwaltney OT pumps, Tod’s wrap bracelet and Pashmy Tracolla bag

DKNY blazer ($395), at Macy’s. LACOSTE cardigan ($145), at Lacoste, 835 North Michigan Avenue. IZOD polo shirt ($34), at Carson Pirie Scott, Edens Plaza, 3200 Lake Avenue, Wilmette. MARNI striped pants ($630), at Blake; and Barneys New York. MARIA SHARAPOVA BY COLE HAAN Air Gwaltney OT pumps ($198), at Cole Haan, 673 North Michigan Avenue. TOD’S wrap bracelet ($1,095) and Pashmy Tracolla bag ($1,095), all at Tod’s, 121 East Oak Street.

 

Photograph: Brian Doben

Producer: Nancy Corbett
Stylist: Stacey Jones
Hair & Makeup: Cindy Adams/artists by Timothy Priano
Model: Edda Petursdottir/Supreme
Photography Assistant: Jesper Justesen
Styling Assistant: Stephanie Soong
SHOT ON LOCATION AT Paradisus Palma Real Resort, Punta Cana, Dominican Republic, paradisus.com.

 

Bottega Veneta tunic, pants, and hairband, Lana Jewelry Sunrise hoops, Adidas Wooster watch, Pour La Victoire shoes

BOTTEGA VENETA tunic ($1,250), pants ($980), and hairband ($120), all at Bottega Veneta, 800 North Michigan Avenue; and Ikram. LANA JEWELRY Sunrise hoops. ADIDAS Wooster watch ($60), at Macy’s. POUR LA VICTOIRE shoes ($280), at Veruca Salt, 521 North Kingsbury Street and 1921 North Damen Avenue.

 

Photograph: Brian Doben

Producer: Nancy Corbett
Stylist: Stacey Jones
Hair & Makeup: Cindy Adams/artists by Timothy Priano
Model: Edda Petursdottir/Supreme
Photography Assistant: Jesper Justesen
Styling Assistant: Stephanie Soong
SHOT ON LOCATION AT Paradisus Palma Real Resort, Punta Cana, Dominican Republic, paradisus.com.

 

Chris Benz Rangoon cargo dress, Nicole Miller Collection dress, Ralph Lauren Black Label Evelyn pants, Kenneth Cole New York High Patential bag, Kara BY Kara Ross cuff, Tod's lace-up heels

CHRIS BENZ Rangoon cargo dress ($1,495), at Chalk Boutique. NICOLE MILLER COLLECTION dress ($245), at Nicole Miller, 1419 North Wells Street. RALPH LAUREN BLACK LABEL Evelyn pants ($1,798), at Ralph Lauren, 750 North Michigan Avenue. KENNETH COLE NEW YORK High Patential bag ($269), at Kenneth Cole New York, 540 North Michigan Avenue. KARA BY KARA ROSS cuff ($295), similar styles at Frances Heffernan. TOD’S lace-up heels ($725), at Tod’s.

 

Photograph: Brian Doben

Producer: Nancy Corbett
Stylist: Stacey Jones
Hair & Makeup: Cindy Adams/artists by Timothy Priano
Model: Edda Petursdottir/Supreme
Photography Assistant: Jesper Justesen
Styling Assistant: Stephanie Soong
SHOT ON LOCATION AT Paradisus Palma Real Resort, Punta Cana, Dominican Republic, paradisus.com.