MORE: How has your style evolved in the past 15 or so years?
VERONICA WEBB: My style tends to change focus to fit what I’m doing in my life. What stays the same, more or less, are the silhouettes and the quality of what I buy as well as the color palette. What’s changed is that my style is much more personal. I don’t shop the trends in the way I used to. I like to buy something that drives me wild because it’s so well made and so comfortable, and then I’ll wear it and wear it and wear it until it’s been worn so many ways it always seems new.
 
If your style is more distilled now—you know what works and what doesn’t—what are some of your rules when shopping? What do you look for, what do you always avoid, etc.?
I always look for things that can do double duty. Athletic wear that’s nice enough to use a cami under a cardi or a blazer, or performance tights that are pretty enough to use as leggings or stockings with a shift dress or a tunic. Whatever I buy, it has to "matter," and I think of things in suites, like a tote, clutch, sunglasses, scarf, earrings, belt, ballet flat. The real trick is finding fabric weights and colorways that cross easily from season to season. You can’t do it all at once. You have to remember what’s in your closet at all times when you’re buying new clothes and collect an accessories wardrobe over the years. I hope my kids will have the same philosophy about clothes. Considering what they’re going to inherit from me, they should!

Do you have a go-to uniform—a combination of things that just work for you, no matter what?
Madewell jeans—they fit my waist, cover my derriere, accommodate my thighs and look totally polished. And the bonus? The price is right! Also, A-line dresses and skirts are great with a scoop neck.

What are your most beloved items in your closet, the things you’ve worn for years and still love?
Anything and everything from Alaia and Mizrahi, who are like family to me.  My Levi 501s. Tuleh sweaters.

Any fashion rules for over-40 women?
You probably already know your style and have a lot of fabulous stuff in your closet. If you’re like me your body probably started to change in your thirties, and then once the kids came the uphill battle started to maintain the status quo. Because I have a tendency to gain weight, I make sure to drink a lot of water and try to be conscious not to gain more than five pounds before I take control of the situation, by adding a few more veggies and eating fewer carbs. For me, a wardrobe is an investment that pays off when I can get dressed in a few minutes without having to think about what fits and then go though my day feeling comfortable and confident.

What should women focus on and what should they ignore when dressing or shopping?  
Focus on what’s good first. Your legs, waist, shoulders, skin, whatever it is—dress and shop with highlighting your best features in mind. Avoid thinking about what’s wrong. Chances are you won’t be able to do much about it in the time you have to get dressed or pick out a dress in the store. In that case keep it simple: Get a shift dress and change it up with scarves and accessories; do something to get yourself out of that rut, like look at art or take a walk with a friend. As women, it’s really hard to remember sometimes we’re not the sum total of what we do for our families and what other people tell us we "should" look like.

Do you have any shortcuts to great style?
What’s your favorite color? Be daring and buy something unexpected in that color, like purple shoes or a yellow purse, and wear it a million different ways. Get three things that are cut perfectly for you—pants, a simple dress, a shirt in black, gray or navy—and let the tailoring be the background.  

What are the best cities to shop?
New York, Paris, Dallas, Miami, London.

The best places to find an inexpensive treasure?
Your own closet. Madewell.