How to Wear It

I like to think of us as the self-help generation. From business books like "In Search of Excellence" to Dr. Spock's parenting books – with plenty of Oprah thrown in-between – we've had great self-help resources to turn to when it comes to most of life's questions.

And like it or not, fashion after 40 is full of questions.

So, here, for those of you who want to have an easy guide to how to wear key pieces without looking foolish, is a guide on How to Wear It:

• Boots — I probably have a boot fetish, because that's the one thing I buy lots of, from furry slip-ons to cowboy boots. Most boots work for our age, except for the floral-dress-and-cowboy-boot look that Taylor Swift has popularized (I don't care if Christie Brinkley wears it, it's still too young.) 
• Fur Vests — Have you been avoiding fur or fake fur because you weren't sure how to pull it off? It's an inexpensive way to recharge your casual pieces and elevate your look. Just make sure you only wear one piece of fur at a time or you'll risk looking like a grizzly bear.
• Belt  — From skinny little belts to wide leather belts, this simple accessory can alter everything from your waistline to the proportion of your entire outfit. You can even make a short-waisted torso look longer with a hip belt or create an hourglass figure by simply wearing a belt.
• Hats  —I've been thinking about the power of a great hat ever since Aretha Franklin wore that bow hat almost two years ago to the inauguration. Since then, the whole world's gone fedora-crazy. Almost any hat works for us. Almost.
• Longer skirts - You might be tempted to think that longer skirts make everything easier, but the truth is we've all become accustomed to wearing our skirts at or above our knees so everything – from tops to shoes – reflects that. But with a few adjustments, you can incorporate longer skirts into your closet, too.
• Sunglasses — You would think something innocuous as sunglasses would be simple to carry off. Why, then, do so many older people wear crazy-looking shades? Sylvester Stallone wears purple shades, Sissy Spacek wears old-fashioned round rims and Nic Cage wears mirrored sunglasses. Ick. But there are plenty of Dos to learn from as well.
• Menswear  — Menswear is trendy right now, but the truth is it's a classic way to look strong and sophisticated. White shirts, vests, camel and boy blazers are some of the pieces you can mix into your over 40 wardrobe with ease. My favorite menswear piece right now are oxfords (although I don't wear them with socks showing like the youngsters.)
• Layers — Do your layering efforts make you look more like a marshmallow than a model? It could be that you aren't layering in a way that's modern – or more important – flattering. Keep it tonal and lightweight and you'll pull it off with ease.
• Long scarf — I'm crazy for long scarves because they look so chic when you add them to any outfit. And, since they are removable, they make great practical sense for those of us who are freezing one minute, then hot flashing the next.