Casual Holiday Outfits With Velvet Leggings

Many of us may be celebrating our holidays quite differently this year, but that doesn’t mean we can’t wear things that make us feel special. Let’s face it, 2020 has been the pits in so many ways, we need to wear clothes that make us feel good about ourselves.

Whether you’re seeing friends, staying home with close family, or spending the holidays alone, a comfy outfit in a luxe fabric feels festive and just right for the season. I’m back today with my stylish friend Cindy, for our monthly fashion edit over 50 to give you some outfit inspiration.

This month we’re stying these velvet ankle leggings. Leggings aren’t every woman’s cup of tea but I believe they can be worn in a classy way by following a few guidelines. Here are my style tips for how to wear leggings – The Modern Way To Wear Leggings After 50


fashion blogger jennifer of a well styled life wearing white tunic and velvet leggings

These Eileen Fisher velvet leggings are a nice soft fabric at a great price! Plus here. They have plenty of spandex so will snap back after sitting and bending. The website says they’re re oversized by design so I went down to an XS which is perfect (I usually wear S in their stretch pants).

The leggings are made using recycled polyester which just feels right in this day and age of conscious consumerism. They have a nice high rise which I always appreciate because it helps keep the muffin top under control.

Here I’m styling them with a crisp white tunic, a vintage velvet scarf, and some open toe shooties., (a bootie/shoe hybrid). I added gold tone Labradorite earrings and a statement necklace to dress them up a bit. I would wear this look to someone’s house for dinner…if we were going anywhere.


over 50 fashion blogger wearing dean davidson earrings and necklace with white shirt

I don’t see velvet scarves that often so cherish the few I have. They’re soft around the neck and add a luxe feel to anything you’re wearing. BTW, a reader suggested I try Kosas lipstick and I’m hooked! This Rosewater color is the perfect everyday shade and the formula is incredibly moisturizing…without being goopy! I love it.

Dressed Down

I dressed the velvet leggings down here with my version of the popular combat boot and a tunic sweater. I don’t go full-on combat boots because they just feel too “tough” for my style. Plus, I wear a size 9 1/2 shoe which at 5’4″ makes them feel too large for my body. This pair feels just right to me and has been a workhorse in my wardrobe two years running now. Here’s a more budget-friendly pair of combat boots “lite”.
relaxed holiday outfit with velvet leggings, tunic sweater and plaid scarf on jennifer connolly of a well styled life

I added a vintage pin (similar) to give a bit of sparkle plus it helps to keep my scarf from shifting around. I read the other day that brooches were out of style. Bunk! If that’s true, I’d like to know why so many brands are carrying them;). Vintage and unique pins are a great way to add a personal spin to your outfit. They’re one of my favorite things to dig around for at flea markets etc.
fashion blogger jennifer connolly of a well styled life wearing blue sweater tunic, plaid scarf and snowflake pin


No matter where you are or aren’t going this season, a pair of velvet leggings are a great option. You can dress them up or down plus they feel cozy just for hanging at home.

Now let’s head over to Cindy Hattersley Design and see what magic she worked with velvet leggings! I know I am always inspired by how she puts her looks together.

Do you have velvet leggings?


This post may contain affiliate links which won’t change your price but will share some commission.


  1. Debbie
    November 15, 2020 / 5:27 am

    Assembling a festive, yet comfie outfit for Christmas holidays is something I love doing as well. If we end up home with fewer family around us, the FaceTime look will be important too.
    I have chosen an outfit the reverse, though not opposite to yours. It includes a black velvet tunic hoodie that I picked upon sale last year and haven’t worn, and patterned bottom- either my Roots flannel black & ivory check pj pants, or a pair of dress pants in a black glen check in the shape of track pants with an elastic waist. Ballet slippers or my cozy suede moccasins will keep me standing when clean up time comes. Now all I need is a black or classy apron- something I too often forget.
    Let’s not forget at least a serum and tinted CC cream, if not full makeup too. Cameras abound and hopefully children, grandchildren or close friends will too, if we lock down Nov/Dec.

  2. Joan
    November 11, 2020 / 3:57 pm

    A very timely article! I just purchased velvet leggings from Chico’s. They fit great but I’m debating whether to keep them. Styling them for more casual looks is where I’m challenged. No combat boots for this Florida girl. I understand that leggings require long tunics. Using a long ruana or sweater over a shorter top is impractical for an at home look. Actually wearing “nice” clothes of any type while cooking dinner would be uncomfortable and runs the risk of spills, etc. Any tips about how/when to wear nice clothes at home? Are you wearing them while still doing household tasks?

  3. Sandra Sallin
    November 11, 2020 / 3:44 pm

    I wear leggings all the time. I love them paired with a long tunic. My closest thing to velvet is pair with a tuxedo stripe up the side of the leg. I wear them dressy and casual. So I’m right there with you.

  4. Lisa
    November 11, 2020 / 2:09 pm

    I love the look with the combat boots, thank you. I have very skinny legs and chunky boots make me look (and feel) ridiculous. That pair are a great option. I’m writing from Australia and love waking up to my morning post of what will be in for us next season. Those velvet leggings look lovely. And comfy.

  5. cindy
    November 11, 2020 / 1:23 pm

    I cannot believe you wear a 9 1/2 shoe and you are so tiny! You really look great in blue.I really like those boots. Do they have plenty of room in the toebox? I would love to try them if so. This was fun. It is always a challenge trying something new.

  6. Joanna
    November 11, 2020 / 9:37 am

    I occasionally wear leggings with a long top around the house. It’s rare for me to wear them outside unless I pair them with tall boots and a long coat. I’m more of a jean kinda girl.
    Those velvet leggings are perfect for feeling a little dressed up while celebrating the season at home. Blue is definitely your colour, Jennifer. You look radiant!

  7. Claudette
    November 11, 2020 / 9:04 am

    I enjoyed the way you showed the white blouse and blue sweater with the accessories. I live in rain country and so appreciated the various boots you featured. I love slip on shoes so when fall/winter comes it is hard for me to find comfortable shoes that work well with rainy days.

  8. diane
    November 11, 2020 / 8:54 am

    As one of your “older” followers, I’m hesitant to try leggings, but velvet intrigues me. And the blue sweater with the lovely blue plaid scarf is striking. I love how you “finish” with look with a pin, a necklace or the right earrings.

    You always inspire me to dress well instead of the “sloppiy, just going to the post office” style that abounds. And I’m off to shop the lipstick brand you mentioned.

  9. Jacki
    November 11, 2020 / 8:49 am

    I am personally not a fan of the leggings look at this age (and I look good in them) for anywhere other than the gym, around the house or occasionally for a quick trip to the grocery store. Reminds me of what my late mother wore– I didn’t like the look on her and I don’t like it on me. Slim fitting casual pants–absolutely– but leggings might as well be opaque tights.

  10. Jane
    November 11, 2020 / 7:33 am

    I don’t have velvet leggings but I did buy faux suede slim pants. They serve the same purpose but I can still balance my shape with a little extra fabric in the leg. I love using your pictures and suggestions as a starting point to dressing myself in affordable clothing that I can source locally.

    • Jennifer
      November 11, 2020 / 8:22 am

      I have some faux suede leggings that I adore. I’m thrilled you interpret my ideas and make them work for you. Bravo!

  11. MP
    November 11, 2020 / 6:42 am

    I like the look but the price $138?

    • Lorie
      November 11, 2020 / 7:30 am

      Anyone else having difficulty seeing Cindy Hattersley’s site? It is blocked by an overlay.

      • Jennifer
        November 11, 2020 / 8:21 am

        I didn’t have a problem. Let me check on my laptop.

    • Jennifer
      November 11, 2020 / 8:20 am

      The widget has other options for you.

  12. Gail Baldree
    November 11, 2020 / 6:36 am

    Broaches are back! During Covid with all the Zoom meetings a beautiful broach or necklace makes a statement!

    • Jennifer
      November 11, 2020 / 8:19 am

      Yes!! I couldn’t love them more.

    • Debbie
      November 15, 2020 / 5:15 am

      Thanks for the reminder!

  13. Diane B
    November 11, 2020 / 6:21 am

    I love the look of the velvet leggings on you. That blue sweater is divine and with the scarf….. I for one don’t think broaches will ever be out of style, maybe out of ‘fad’ but style is how you wear them. I cannot have velvet anything in out house as we have 3 cats and one of them is white. There are lint rollers all over the house and in the car just in case. We are not going anywhere for Christmas this year due to restrictions for household only, so plan on making it a cosy one for two of us.

    • Jennifer
      November 11, 2020 / 8:19 am

      A white cat would mean my entire wardrobe would be beige and white 🙂 Vanessa has a beige pug who sheds so much I need to live with a lint rolled in my back pocket.

  14. Paulette Levy
    November 11, 2020 / 5:47 am

    I really like the velvet leggings with your gorgeous blue sweater and scarf, boot and sunglasses. You look stunning!
    I’m sure those leggings are if the highest quality which makes sense for we over 50/60 women. Thanks for sharing!

    • Jennifer
      November 11, 2020 / 8:17 am

      Thank you, Paulette :). I love these blues.

  15. Gayle Murphy
    November 11, 2020 / 5:43 am

    You mention “whether you’re seeing friends, staying home with close family, or spending the holidays alone,”. I live in Toronto Canada. Population nearly 3M in the city, (over 6 M in the greater Toronto area.) We in Toronto have just been told to socialize with no one outside of the people you live with, so, no seeing friends, and no close family. Don’t go to anyone else’s home, and don’t have them come to yours. So, it’s good that we can dress up for ourselves, to help make where we live festive and joyful.

    • Jennifer
      November 11, 2020 / 8:16 am

      Yes!! I need to dress up for myself. My mental health is definitely boosted when I dress up a bit. Stay safe, Gayle.

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