When I came to Chicago in 1966, television reporters like me were second-class citizens. People were still reading the paper to find out what was news. I kept hearing about this dive called the Billy Goat where all the print guys would go. So I’d stop in once in a while to rub elbows with “real” reporters. Now the tourists come in because they’ve seen the place on television, but if you go at the right times, it still feels like a local headquarters, like ground zero. Plus, it’s cozy and subterranean. Pretty good cheeseburgers, too.

Billy Goat with Bill Kristol
Giamba sequined cotton sweatshirt, $475, and Maticevski polyester skirt, $1,395, Chalk Boutique, 337 Park Ave., Glencoe. Tomas Maier leather belt, $290, Neapolitan Collection, 560 Chestnut St., Winnetka.Leather sandals, $1,545, Christian Louboutin, 58 E. Oak St.Photos: T. Harrison Hillman; Styling: Jessica Moazami
Billy Goat with Bill Kristol
Left: Jacquard jacket, $7,500, and pants, $2,200, Gucci, 900 N. Michigan Ave. Earrings, $99, Swarovski, 845 N. Michigan Ave. Right: Totême silk dress, $460, Chalk Boutique. Gucci fur capelet, $18,000, Ikram, 15 E. Huron St. Earrings, $60, Ann Taylor, 600 N. Michigan Ave. Satin sandals, $995, Jimmy Choo, 114 E. Oak St.
Billy Goat with Bill Kristol
Left: 18-karat gold and pavé diamond ring, $11,900, Lester Lampert, 7 E. Huron St. Dior gold ring, $500, Neapolitan Collection. Ring, $199, Swarovski. 18-karat gold and diamond bracelet, $19,800, Lester Lampert. Right: White gold and diamond ring, $39,000, Van Cleef & Arpels, 933 N. Michigan Ave. Midi ring, $10 for set of 10, Charming Charlie, 520 N. Michigan Ave. 18-karat gold, ruby, and diamond ring, $62,500, Lester Lampert. Elizabeth and James topaz ring, $85, Nordstrom, 55 E. Grand Ave. Rose crystal cuff, $69, Swarovski. Dior painted gold-plated cuff, $1,200, Neapolitan Collection.

Behind the Scenes of the Fashion Shoot