How to Wear Leggings Like a Lady

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.

2017-05-25T16:36:41+00:00 February 16th, 2015|14 Comments

14 Comments

  1. Sooz Weissberg February 16, 2015 at 3:13 pm - Reply

    I love my leggings. I like the long leggings best with knee boots and a tunic length top, but I really enjoyed the idea in your photo of wearing a belted blouse with them, under a jacket with the sleeves pushed up. I think they look great with a tunic top or dress and dresst sandals with a heel, Mostly I would wear black leggings with things, but while traveling to a hip place last year, two pair of patterned leggings “spoke” to me and I brought them home. One is dark-colored, like a chocolate batik print, and the other is white and black WILD graphic. I must admit, I’m not sure if I have ever worn either of these out in public, but I enjoy wearing them to the gym with a long t-shirt, and livening up the navy blue-black crowd there (wink).

    • Linda Waldon February 16, 2015 at 6:20 pm - Reply

      Sooz, I love the idea of wearing a wild legging to the gym! But if you’re feeling sassy, try wearing the patterned leggings with a blouse, jacket, and a scarf to give them a more conservative, put-together look.

  2. pattiw February 16, 2015 at 3:18 pm - Reply

    Yes to leggings. At 50+, my legs are about the only body part left I have to show off!

  3. EZRA February 16, 2015 at 4:18 pm - Reply

    Leggings in the 80’s until now! Not many things work for thirty years. For me my legs are my best asset and I will wear them with anything that covers the nether regions {:) : tall boots, short boots, flashy sandals, high tops, mini skirt, shorts and even heavy socks for a throwback flash dance effect, jacket, shirt etc etc.

  4. Susan February 16, 2015 at 4:21 pm - Reply

    I guess I still think you have to be very brave to wear leggings—and I’m not that brave!

  5. Jo Strausz Rosen February 16, 2015 at 4:28 pm - Reply

    Leggings are a great layering piece under multiple tunic lengths.. add a leather vest and chunky silver jewelry or a longish colorful scarf or sweater coats . Easy for weekend wear or night on the town with boots and B.May bag. Enjoying your systematic beautification of the world. XO

    • Linda Waldon February 17, 2015 at 3:04 pm - Reply

      Jo, those combos sound fantastic! Thanks for the suggestions!

  6. Linda Waldon February 16, 2015 at 6:07 pm - Reply

    Here’s what a reader sent to me via email. She would love to wear leggings, but she has to wear support hose and shoes with orthodics, which leaves out most boots and ALL heels. Does anyone have a solution for her?

    “I love leggings and have a very nice pair with a pleated rib front and back which makes them look like very fitted slacks. Here is the problem I currently have that makes wearing them none glamourous for me(the same problem I now have with all my cloths). I have to wear support hose and orthodics. I am supposed to wear athletic shoes with both. All the cool boots you show your models wearing with leggings are out for me and the leggings crawl up the support hose. The athletic shoes had lurid colors and logos everywhere and make your feet look huge like Minnie Mouse. Any solutions?”

  7. Linda Waldon February 17, 2015 at 8:39 am - Reply

    Susan Bailey wrote: Linda, I LOVE leggings, first they are SO comfortable, beats feeling like you’ve wrapped yourself in duct tape when you sit down with skinny jeans or the like. I have lots of tops that are fun, more dressy or tailored and mid thigh so the best part of your legs are accented. No matter the season, they go with many shoes, sandles, boots, ankle boots and I love all the boot toppers/socks that give you a new look each time, for the boot and/or legging. Also, if I don’t go with a mid thigh top, I throw on a short jean skirt over the leggings and a shirt or vest that goes to waist. I’m just 60 too and it’s fun to get compliments on the combinations that I put together, feel a little sassy and classy and stretches the wardrobe as well. Enjoy your leggings ladies!!!

  8. KC February 17, 2015 at 9:32 am - Reply

    Love the examples you’ve shown in your photos! For a dressier look I also like leggings paired with a softer tunic top and ballet flats!

    • Linda Waldon February 17, 2015 at 3:03 pm - Reply

      Thanks, KC! I love the idea of dressing up leggings with a soft tunic top, great jewelry, and ballet flats.

  9. Anonymous February 17, 2015 at 12:44 pm - Reply

    I’m only 5’1″ and most of the time when I wear a longer top I feel like I look even shorter. How can I wear comfy leggings without feeling like my top looks way too long and my legs look way too short?

    • Linda Waldon February 17, 2015 at 3:02 pm - Reply

      Great question, Anonymous! First, I would shop for Petite/Ankle Length leggings, which will fit you better. Here’s a Style&Co brand from Macys, http://www1.macys.com/shop/product/style-co.-petite-ankle-length-leggings?ID=1011222. For the top, choose a loose-fitting, but not too bulky top, with a v-neck to elongate your top half. Choosing monochromatic colors gives you a longer look, too. If you’re concerned that the top doesn’t have enough definition, add a belt. The shorter ankle-length legging will look good with a flat or low heel shoe. Avoid the shiny leggings, and go for a legging with more structure that don’t show bulges. Have fun and let us know how they work out!

  10. Linda Waldon February 18, 2015 at 7:54 am - Reply

    I wanted to add one more suggestion. If you are not comfortable wearing leggings, consider a straight-leg or skinny pant (like the white jeans Ruby is wearing above). They give you the same silhouette as leggings without the revealing aspect.

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