gold jacket

Ben Goldstein/Studio D

A Golden Opportunity
"This could work if I lose a few pounds."
— Gayle King

"This could work if you vacation in Colonial Williamsburg."
— Adam Glassman
jean skirt

Ben Goldstein/Studio D

Forever in Blue Jeans
"Every woman should have a denim skirt...yes?"
— Gayle King

"Let me see how best to put this...NOOOO!!!!"
— Adam Glassman
flowered suit

Ben Goldstein/Studio D

Not Suitable
"How can you say this Richard Tyler look is dated?"
— Gayle King

"Oh, I don't know; the shoulders, the skirt length, the fact that I saw it on a rerun of Ally McBeal."
— Adam Glassman
yellow skirt

Ben Goldstein/Studio D

They Call Me Mellow Yellow
"This skirt was once very cute."
— Gayle King

"This skirt was once curtains in John Quincy Adams's bedroom."
— Adam Glassman

Keep Reading: Inside Gayle King's Closet Makeover