Denim Dilemma: "Comfort is the most important thing," says Deborah. "I have one pair of skinny jeans that are so tight I can't get out of them by myself—my husband has to help me!"
The Solution: Eileen Fisher jeans that are extrasoft and have a higher rise.
Jeans, Eileen Fisher, $178. Sweater, Equipment, $338. Shirt, NYDJ, $98. Earrings, Dina Mackney Designs. Scarf, Luxe Rachel Zoe for QVC. Necklace and ring, Sequin. Boots, Cole Haan.