You might accurately describe Alyson Walsh as the Alexa Chung of her generation: She prefers wearing a good pair of jeans and a T-shirt over anything too fussy. She writes that she started her blog, That's Not My Age, with one mission: "I've always strongly believed that you don't have to have youth to have style, and I wanted to share ideas and celebrate inspirational women (and men) of all ages."
How to actually do it: "Figure out your go-to, foolproof looks," says designer Nanette Lepore, then seek out variations on that theme. Stumped? Picture the outfits that you feel most comfortable in. Or ask people close to you what you look best in. Once you've zeroed in on what works, find different takes. "I gravitate toward jackets, so I'll do a bomber style, then a silk version, or a denim jacket with leather sleeves," says Minkoff. "Whenever you feel the need to talk yourself into things, that's a red flag that you shouldn't buy them," says Minkoff. If you have doubts in the dressing room, it may help to take a photo of yourself in the item, suggests Aerin Lauder, the founder and creative director of the lifestyle brand Aerin. "It's much more accurate than looking in the mirror."