Do you have a desire to wear leggings, but you’re unsure how to style them?

“Fashion is about dressing according to what’s fashionable. Style is more about being yourself.” — Coco Chanel

Let’s talk about how women “of a certain age” can wear leggings in a sophisticated, stylish way and still be themselves. Leggings have a place in our lives because they’re versatile, comfortable, and fit into a busy lifestyle. I’ve seen controversial articles about how older women shouldn’t attempt to wear leggings — nonsense! My advice? Go for quality legging fabrics and use layering techniques to reduce the chance of looking like a student wearing an over-sized sweater.

Here are some examples of how to wear leggings like a lady:

I am wearing TART leggings with a beautiful goldenrod Equipment Femme blouse, silk scarf and chunky gold necklace. Badgley Mischka handbag and Diane Von Furstenberg boots.

While setting up the photo shoot, our good friend, Ruby Raymond, stepped into Finders Keepers, looking absolutely gorgeous in her Ralph Lauren skinny jeans (which could easily be leggings), Alberto Fermani boots, and Johnny Was blouse. I asked her if she’d let us include her in this style post, and she said yes!

Leggings take on elegance with a crisp, tailored Chicos blouse, relaxed linen jacket with sleeves pushed up, and a silk scarf serving as an artsy belt. Add an Arcadia Italian handbag, Diane Von Furstenberg boots, multi-strand silver and pearl necklace, and I’m ready for a day of shopping in SLO or lunch with the CEO.


Look who I’m going to lunch with! My good friend, Helen Anderson (jewelry designer extraordinaire). Helen is the perfect woman to model leggings because she wears them almost daily in different ways, always looking beautiful and put-together. Here she’s wearing Renaur leggings with a teal Free People tunic and her own jewelry creations.

As you’ve seen, leggings can look elegantly French chic when styling with a crisp blouse and jacket. They can be casually classy with a relaxed tunic top in a great color, fabulous necklace or two, and flat loafers or strappy sandals.

Where can you find leggings? Here are a few suggestions to get you started:

  • Finders Keepers is bringing in a special line of leggings that offer structure.
  • Lysse has different legging styles for all sorts of body shapes.
  • Spanx has a line of leggings that offer structure and control.

Do you wear leggings? How do you style leggings? Please share your thoughts below.