Casual Holiday Outfit

Happy Friday ladies. It is not an understatement to say that yesterday’s comments brought me to tears. Sort of sloppy, almost blubbering tears. I can’t tell you how very thankful I am for all of you. Thank you so much for being here. Together, we have made this a supportive community that I am so proud of. I feel truly blessed.

Cindy and I are being joined by our good friend Tania again this month for our monthly Over 50 Fashion Edit. This month it’s all about holiday dressing.

Kevin and I have a grand total of 1, holiday party to attend this year. Yippee! Knowing me, I will pull out something to wear that I’ve had for years that’s velvet, perhaps subtly sparkly, or potentially fuzzy. For Thanksgiving, I’ll be sitting around a lot, wearing an apron, and eating more than I intend to, so comfort will be the name of the game.

grey j jill top for thanksgiving

I found this tunic at J. Jill last week and am impressed that it’s embroidered rather than stamped. I appreciate that kind of quality because so many brands are cutting corners these days. It comes in misses, petite, womens, and tall. I’m wearing a regular in small. I opted for regular over the petite because I hate having my backside show in leggings 🙂 In fact, I wrote a whole post about The Modern Way To Wear Leggings over 50 here.

woman standing on sidewalk wearinjg leggings and embrooidered tunic top

I love that these leggings have a “tuxedo stripe” of faux leather running down the side. These kinds of stripes down the side of pants and leggings are very slimming. Plus, this touch of vegan leather updates the look without feeling as warm as solid faux leather leggings. Faux leather doesn’t “breathe” so they can be hot when you’re cooking all day:)

These come in sizes XS-XL in misses, petite, women, and tall. I am wearing a regular in small so they run true to size. Leggings can be tricky, but when I stick to good-quality ponte fabric, I am always happy with their look. The necklace was my mom’s, and the earrings were a Christmas gift from my daughter Vanessa, which you see me wear. All. The. Time. The booties are old, similar here.


These booties aren’t super similar, but I just found and ordered them because they come in narrow, medium, and wide with a lower, more comfy heel than mine:) The older I get the less happy my feet are so I jump on shoes that are comfortable, and Rockports are great:)

fashion blogger jennifer connolly wearing casual holiday outfit
 I did notice that J. Jill has brought back this plaid tunic for the holidays.

Now let’s go check out Tania at 50 is Not Old, and Cindy at Cindy Hattersley Design

Thanks for reading ladies and remember to wear what makes you feel confident.


  1. That is a great shade of grey on you!

  2. Wow, beautiful styling. Love this look!

  3. Leslie Adams says:

    I know this is an unpopular opinion but I don’t think faux leather, vegan leather or pleather leggings or pants look good on most people. If they are shiny they catch the light and bring attention to any lumps and bumps, and they don’t seem to hang well and often seem clingy or bunched up. I think yours look better than most, but I wish this trend end!
    I love a tunic that covers my bottom and lady bits.

    1. The shine can be very revealing. I tend to prefer faux suede or I do have a thick faux leather pair with ponte in the back which is more forgiving.

      1. Leslie Adams says:

        I prefer faux suede. I will keep an open mind.

  4. I didn’t comment yesterday, but thank you for showing us that we can look our best, whatever our age and stage of life.

    The biggest compliment I can pass on to you comes from my husband. He thanked me for making the effort to look good during this pandemic. It lifts his spirits. Reading your blog helps me do that.

    1. Awesome!! I bet that makes you feel great!

  5. Beautiful outfit and perfect for the upcoming holiday season. You always look lovely in whatever you might be doing,I.e. the video with Velcro rollers, loved it….only a woman who is truly confident and loving her life could pull that off..👏🏻👏🏻🤩🤩🤩🤩 have a great weekend Jennifer

    1. You’re so kind, thanks, Dianne. A fresh new robe does give a gal confidence, don’t you think?

  6. I like both of those tunics on you and I need to check out those boots. I think J Jill has some really cute things right now. I can’t believe how you pulled this together while being so busy! You are amazing!

    1. You are the amazing one, my friend. I need you to come give me pointers on accessories:)

  7. Gwen Ewing says:

    I always enjoy your blog. Thanks for the time you put in for us❤

  8. I love this grey outfit. The top looks a little flowy at the bottom which will cover my tummy. I own charcoal pants so that is perfect. Charcoal is my new black. That necklace looks so good with the top. Just hope top is not thin, thin. Thinnish is okay but thin, thin is not. I’m trying to picture this 79 yr old body in leather leggings. Doesn’t compute. LOL

    1. It’s the weight of a very heavy tee, not a sweater.


    Gosh, Jennifer, most of us don’t want a design that draws attention to our hips and surrounding area! I like to look for tops that keep the interest closer to my face or upper body…

    1. That’s where jewelry and accessories come to the rescue to draw the eye up to your pretty face.

  10. I forgot to say , in my last post, that I live in Northern California. Now about your outfit for today…that looks especially cute on you. I also think through my outfits when I am cooking. Many times I opt for a thinner cotton top as tend to get really warm during our thanksgiving feast. As always…you keep giving me good ideas!

  11. Great outfit ideas, Jennifer!

    Thank you for pointing out the embroidery on the tunic- it’s the sort of thing that is very useful to know!

    I’ve been reading your blog probably for over 3 years. I’m probably around your daughter’s age, my coloring is very different, and most of my clothes are different in style- I like more romantic style, dresses, flowing long skirts, etc.

    And yet, yours is one of few blogs I read. Your authenticity is refreshing, and I appreciate that you tell it like it is. I think it’s rare. Also, my favorite posts are when you try to fix what a mannequin is wearing, and I appreciate that you don’t just post perfect combinations. If it doesn’t work, you explain why, and that’s very helpful.

    Please keep being you.

  12. Hi Jennifer! I got busy yesterday and forgot to comment. (It was a big day for this retiree—Covid booster shot and dentist appointment! Lol) I love your blog for many reasons: you’re an actual stylist, so you know what you’re talking about; you’re very close to my age; you’re petite like I am; you show “real-life” clothes; you’re very honest about your own challenges as you get older; you have a great sense of humor and don’t take yourself too seriously; you provide us with important and timely information on products and aging; etc. I could go on, but please know that you’re one of my very favorite bloggers, and I appreciate you!

  13. Hi Jennifer~ Love your hair today! I have been searching for a plaid shirt, love that one. Thank you for inspiring me.
    Have a blessed day!

    1. Thanks Mary Ann. My hair is on a journey of its own and sometimes only a gorilla clip with tons of hair spray will help 😀

  14. Many of my same thoughts were expressed yesterday. I have all the similar hair, skin, body issues that you do. Yours is the first blog that I can really relate to. I have discovered so many helpful ideas & products!
    I have the JJill plaid shirt from last year & it’s just about time in the Desert Southwest that I can wear it, as well as, other jackets & sweaters that I covet.
    Thank you so much for your time & effort that goes into creating this blog!

    1. It’s such a great shirt!!! Thank you

  15. Tania Stephens says:

    I am all about comfort for the holidays. Your vegan leather leggings look great, so I’ll have to check those out!

    1. Thank you joining us Tania. Your outfit is so cute.

  16. I love the ideas of casual and simple. I have the plaid shirt from Jill in my closet from last year, but I will go look for tunic.

    Thank you for your ideas.

  17. Marian E. says:

    I really love the way you have your hair pulled up in the fair aisle tunic pics. Such a nice look! Can you post a tutorial on how you did this?

    1. My hair is doing nothing I expect these days 🙂 so I simply teased the back and too lightly and smoothed into a gorilla clip in the back. Then I sprayed the heck out of it with a light hair spray.

  18. Barbara Weiner says:

    Heard about you from Tania, 50 is not old. Love your look!

  19. Paulette Levy says:

    You deserve and have earned all the wonderful reasons we love your blog. Thank you for coming into our homes every week! (Every day)! You bring advice but also a friendly visit.

    1. Thank you so much Paulette. You’re the very best!

Leave a Reply

Your email address will not be published. Required fields are marked *