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How to Rock Creative Holiday Looks after 50

Today I am joining my friends Jennifer from A Well Styled Life and Tania from 50 isn’t Old. We are talking about Holiday Fashion. Will you be dressing up for the Holidays?

Now that we’re in our 50’s 60s (and beyond), we have the confidence and freedom that comes from not being a slave to fashion and being comfortable in our own skin. How to dress for the Holidays? I believe the Holidays will be different than last year, but still like years past (whatever the new normal may be). Many of our holiday celebrations will still be small and casual. I thought I would feature a few casual looks and a couple of fun ones.  I don’t know about you but I won’t be attending any formal events (wait did I ever?).  Let’s take a look at How to Rock Creative Holiday Looks after 50.

how to rock creative holiday looks for women after 50

I wore this skirt that I purchased while in Florida from a small boutique Nicole Paloma Designs. I personally would not wear this skirt without either leggings like I am showing here ( or with boots like I showed you here ) unless it was longer in the front. I am sure you can order a custom length if you contact Nicole. I wore it for Mary Ann’s birthday party with my new comfy combat boots (that you guys love haha). I am wearing it with a necklace from Love Heals (an anniversary gift several years ago from Steve), velvet birdies, and a BR turtleneck.

cindy hattersley in nicole paloma skirt


I featured this J Jill Sweater in my outfit of the week a couple weeks ago and it has been a favorite with all of you for good reason. I have ordered the plum and the green. This is my absolute favorite sweater this season. I am wearing a Small. The petite was too short for me. I like the length for coverage. I am wearing it with faux leather pants from WHBM, my new Rocki Gorman earrings (an early b-day present from Steve). Rocki’s shop is located in the beautiful La Fonda Hotel in Santa Fe. She is also having a 15% off sale right now. These earrings make a statement so I just added a couple of my Native American bracelets and called it good. The boots are from Gentle Souls and are super comfortable (note the wide toebox).


Here I am wearing the versatile J Crew sweater pants that you saw in my post Fall Fashion the Knitwear Trend., with an old Zara velvet jacket and the Gentle Souls Emma boots. I accessorized with the same fabulous Rocki Gorman earrings, a navajo pearls strand & cross. I am wearing another pair of boots I picked up this year the Gentle Souls Emma.

cindy hattersley in vintage zara jacket j crew sweater pants


This skirt was inexpensive $29 and fun. You read about it in my How to Wear Combat Boots Over 50 Post here.It comes in many other colors. I think you could pair this with a motorcycle jacket as well. If I were hosting a party this year I would definitely wear this.  We need a little fun in our lives right now don’t we?



This tulle skirt my daughter wore to the prom one year. I finally had to pitch it in the move because it had too many tears. You can pick these skirts up inexpensively. There is no need to buy an expensive one because they can get torn farely easily. Here I am wearing it with an older mustard turtleneck, a suede obi belt, with a vintage rhinestone brooch. Simple rhinestone earrings and you are good to go.

Cindy Hattersley in Tulle skirt and Madewell Mules


You have seen this scarf from IBU (available in a dark red and an Ivory currently). It is a favorite of mine. Here I am wearing it with Spanx faux leather leggings, an inherited concho belt, and my trusty bed stu boots. FYI mine got lost in the move and I found a pair of Bed Stu Manchesters on Ebay (I wanted a broken-in pair. because of my bunion.)


Thanks for reading How to Rock Creative Holiday Looks after 50. How will you be spending the holidays this year? Let’s pop over and visit Jennifer and Tania to see what they have in mind for the holiidays



Reader Interactions


  1. Zsa Zsa says

    Ms. Cindy, all the outfit are great! My faves are the leather pants, the leggings and the grey tulle skirt!

  2. NCSue says

    Love your style! i have the JJill sweater in green & also love it. Plan to order plum. How will you style that color?

    • Cindy Hattersley says

      Hi Sue

      When I get the plum I will let you know! I find that hue is really good with gray hair. Never embraced it before.

  3. Judi says

    Combat boots are everywhere in Europe!
    Every age, every combo.
    I bought some here and especially love wearing with leggings and a sweater dress.
    I guess the boots will sit it out once I hit home in Florida. Mostly bought for travel.
    So comfy for walking old towns in Europe and you look very “on target” in your outfits.

  4. Karen B. says

    Hi Cindy,
    You pass along such great fashion ideas. It’s fun to see the combinations you pull together. I look forward to the holidays. We always enjoy at least a couple of events where it’s fun to “dress up” for.

  5. Lauren says

    Finally a picture of you without the sunglasses….hoping this “no sunglasses” continues. I think I remember reading that you wear sunglasses because your eyes have a few wrinkles…..well guess what so do must of your readers so please join us as we age with whatever we get in terms of wrinkles

    • Cindy Hattersley says

      Hi Lauren

      Ha! Almost everytime I photograph outside without sunglasses I look like I have my eyes closed. It’s the hooded eyes.

  6. Jill Miglin says

    Inspiring. Unfortunately I was unable to locate the scarf, like you’re shown wearing with the faux leather leggings and your boot, on IBU. Love it.

    • Cindy Hattersley says

      Hi Jill

      It is not available in this color this year. It is available in an off white and a black and red which is very pretty.

  7. Nan of TN says

    The Nicole Paloma look is one of your best! Along with the IBU scarf donned as a vest: classic CH style. Awaiting Eileen Fisher’s organic Peruvian cotton sweater knit pant in moon grey I recently ordered. Isn’t it wonderful how much comfort factor is being incorporated into current fashions? Just received a gorgeous grey baby alpaca wool Eileen Fisher coat in pristine condition from a seller on eBay and it is the softest, coziest coat I own now.

    Here’s wishing you an early Happy Birthday, Cindy!

  8. Wren says

    Love revisiting your inexpensive skirt and combat boots. I think you really rock that outfit!
    Your hair looks super good in the pic where you are wearing your Nicole Paloma skirt. And a husband who gifts you with jewelry…. how special
    I may wear my JCrew knit wide leg pants like yours on Thanksgiving. Elastic waist and lots of give everywhere!

  9. Gray says

    That striped skirt is the cutest thing! You can pull it off with your long torso! I might be too short waisted… Such a cute look.

  10. Pamela Whitcomb says

    You are so darned cute! I think my favorite on you is the Nicole Paloma skirt. You will rock the holidays in that outfit!

  11. Leanne Gillespie says

    Soooo happy to see a Nicole Paloma featured! She is my favorite designer of all time with the most comfortable versatile clothing ever. What ever you buy from her amazing shop can be worn with cowboy boots , heels, flats or flip flops. I’m lucky to live in Santa Rosa Beach FL and have access to her inspiring store and fashions. Always something new happening with her!

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