Building A Casual Weekend Outfit

Last weekend, I once again tried nude lipstick and proved to myself, that I need more color on my mouth. I love the sophisticated look of a nude lip but the older I get, the softer my coloring becomes so nude lips wash me out. I simply look much healthier with a brighter color on my lips so I’ll happily go back to my new favorite Rosewater pink and perhaps dabble with some soft raspberry for the holidays. Will you be wearing red?

Related -Red Lipstick: The Edit for Fair Complexions

Anywho…today I have an outfit for you that will be on heavy repeat for me and would be great for Thanksgiving Day. Let’s start at the top…this gorgeous scarf! I never used to enjoy wearing plaid, but now that I’ve broken the ice so to speak, I am loving it in everything!fashion blogger jennifer of a well styled life wearing plaid scarf over aqua sweater with blue jeans

Perhaps my secret desire to live in a rustic cabin by a lake is influencing me, but plaid just feels perfect for this time of year. Sheesh…I look at this photo and my hand twitches to add some brighter lipstick. I like to wear plaid in small doses but in this pretty color combo…I could wear it head to toe.  over 50 fashion blogger jennifer connolly of a well styled life wearing blue jeans, plaid scarf and aqua sweater

My funnel neck tunic sweater is the kind I normally wear over skinny jeans or my favorite jeggings. It’s got a straight boxy cut yet I’m loving the proportion with these barely bootcut jeans. I know most of you are faithful to your skinny jeans and I love mine too, but a small bootcut allows you to pop your pant leg over your boot, thereby elongating your leg.

Related – How to Look Taller and Slimmer

fashion blogger jennifer connolly of a well styled life wearing plaid scarf, boot cut jeans and tunic sweater

Some boot cut jeans are closer to flares but these are closer to a straight leg. They’re slim through the leg until just below the knee where they flare out slightly. I find this shape so versatile, I now have this jean style in three different washes.jennifer of a well styled life wearing dean davidson earrings plid scarf and aqua sweater

This scarf is so vibrant, I simply added my Dean Davidson Labradorite earrings and called my outfit done…other than brighter lipstick.

Do you reach for plaid this time of year?

What are your plans for Thanksgiving?



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  1. Janey
    November 21, 2020 / 12:54 pm

    Love that top color! Wearing masks for the past few months has been a challenge with lipstick.

  2. Linda D.
    November 21, 2020 / 6:42 am

    I love plaid and always have. I love today’s outfit. Also a Canadian and not living in a major city I can only enjoy your fashions from afar but you are an inspiration.
    I have an issue with lipstick ending up on my teeth and have found the only one that stays put to be Merle Norman’s Lip Pencil Plus. It is a liner and lipstick in one. The only time I’m now putting it on is for Zoom calls. It certainly brightens your appearance on the screen.

  3. Linda D.
    November 21, 2020 / 6:36 am

    I am a fan of plaid and always have been. Love the outfit you have on today. Also being a Canadian and not living in a major city I only get to enjoy your fashions from afar.
    I have an issue with lipstick ending up on my teeth. The only one I’ve found to stay put is the Merle Norman lip pencil plus. It has the liner and lipstick in one. The only time I wear it now is for Zoom calls, it certainly does brighten your look on the screen.

  4. Maria
    November 21, 2020 / 1:26 am

    I see the photos with a nude lip and love it on others but it totally washes me out especially since I stopped colouring my hair. The hair is a nice silver and a bold red lip makes me feel happy. With the mask wearing I blot it off before putting on the mask and the moment the mask is off the lipstick is touched up.

  5. Elaine @ Following Augustine
    November 20, 2020 / 5:17 pm

    I love the colour of your sweater and the scarf looks lovely with it! I love my skinny jeans, but I also have a couple of pairs of bootcuts similar to yours that I like to wear with booties.

    • Jennifer
      November 20, 2020 / 8:55 pm

      I really prefer boot cut with boots:)

  6. Lin
    November 20, 2020 / 3:51 pm

    Love the sweater, scarf and jeans. Sweater color is wonderful.
    I wear a light mauve lip stick (artistic rouge cream) from Sephora. It is just enough color to look natural but bright enough to pop.
    We have similar coloring, so you might like it.

    • Jennifer
      November 20, 2020 / 8:54 pm

      Thanks, Lin, I’ll check it out.

  7. Barbara
    November 20, 2020 / 3:38 pm

    You look great! Where did you get those boots?! Info, please. 🙂

  8. Gerri
    November 20, 2020 / 11:15 am

    I am 72 on Tuesday, and have to tell you I hate lipstick! I only have ever worn it on rare occasions, and regretted it every time! As I have aged, I have inherited my mother’s puckery lips, and lipstick just makes them look worse!
    I love the jeans you showed in this post! During the winters on the mainland, I was always into boots and jeans. My go to outfit! Cashmere sweaters, just like you. I enjoy your posts.

      • Karen
        November 22, 2020 / 8:15 am

        I am almost 60 and have the same old lady lip lines that lipstick runs into and looks terrible. I found out that if I line right outside my lips fist with a clear wax pencil (I use either of two different brands) it stops the issue all day! Not necessarily true with mask use. I don’t use vibrant colors but with my olive skin I use I think it was a Lancôme Rose Brun-? Anyway, something for just a bit of depth and color.

      • Karen Cooley
        November 22, 2020 / 8:20 am

        Sorry I spelled your name totally wrong. Have t had my coffee yet!

  9. Julie Traxler
    November 20, 2020 / 11:13 am

    I also cannot wear nude lipstick as much as I want to! Also, You jeans are mine too…except I like your color better. Checking on the darker ones.

  10. Rebecca
    November 20, 2020 / 10:08 am

    Even though I am definitely not petite your suggestions still resonate with taller women who want to look slimmer. You once referred to what you called “grandma jeans”. Can you please describe what you mean by that?

    • Jennifer
      November 20, 2020 / 10:31 am

      Hi Rebecca, I’m pretty sure I have never used the term “grandma jeans”. I have often use the term “mom jeans” which is a very common descriptive term for a certain style of high-waisted jeans. Now they’re become very popular.
      They are typically high waisted and loose fitting.

  11. Carolyn Ball
    November 20, 2020 / 9:32 am

    What purse are you carrying?

    • Jennifer
      November 20, 2020 / 10:23 am

      My purse was a gift from a dear friend, many years ago. The brand is Marc jacobs but I have not seen one like it for many years. This ones looks very similar.

  12. Rose
    November 20, 2020 / 9:22 am

    Love your outfit, looks so comfy. I would love to wear that on Thanksgiving! I’m a big fan of plaid this time of year. Sometimes I will tie a plaid shirt at the waist as I’ve seen you do. I keep forgetting we don’t need to wear lipstick with a mask but just can’t not wear it. I also need more color or look washed out.

    • Jennifer
      November 20, 2020 / 10:19 am

      I’m with you, Rose. I wear lipstick, rain or shine, mask or no mask, staying in or going out!

  13. Carolyn
    November 20, 2020 / 9:06 am

    What purse are you carrying in shoot.

  14. Lily
    November 20, 2020 / 8:35 am

    I have a lot of plaid flannel shirts but I’m just not feeling them this year.
    As for Thanksgiving, I will (hopefully) just stay home. I’m fine with an easy meal with just my “bubble”. Think I am going to go crazy this winter with the Covid situation.

    • Jennifer
      November 20, 2020 / 10:18 am

      Hopefully, we will get some relief soon. Hang in there, Lily!

  15. Kathleen Meyer
    November 20, 2020 / 8:30 am

    WIth wearing a mask every time I go out to go somewhere I have not been wearing lipstick at all. Hopefully soon!

  16. Suzi
    November 20, 2020 / 8:15 am

    Jennifer, can you provide sizing on your jeans and the sweater. You are the only women on a life style blog whose shape/size is similar to mine. Many times I have to order 2 petite sizes and 2 regular sizes in an order to find a correct fit. No Talbots in the San Diego area carry these jeans. 🤷‍♀️
    Thank you for shopping and styling for us.

      • Pam Sledge
        November 21, 2020 / 6:58 pm

        What size are you wearing in the pistachio heather funnel neck tunic sweater from J Jill?

      • Jennifer
        November 21, 2020 / 7:54 pm

        I am wearing a petite medium

  17. Henderson, Linda
    November 20, 2020 / 7:59 am

    The sweater and scarf combo looks wonderful on you. Love the colors.

  18. Carolyn
    November 20, 2020 / 7:48 am

    I’m with Bea. I recognized the clothes. Love your look. Can you please tell me what size sweater you are wearing. I will be ordering online and I’m using you for my reference. Thanks.
    I have to have color on my lips now or I look so washed out and o-l-d !

      • Pam Sledge
        November 21, 2020 / 6:59 pm

        Thank you – it looks beautiful on you, along with the plaid scarf.

  19. Barb
    November 20, 2020 / 7:08 am

    Good morning. I like the outfit you are wearing and loved the one from the other day with the navy sweater and fitted sweat pants, along with those great boots. However, i live in Canada and Talbots does not offer any options for us other than paying the exchange rate along with custom and excise taxes, as well as the delivery/mail charge. I don’t mind paying for the clothing, but I draw the line at paying that much extra money for which I get nothing, really. I had the outfit in my cart, but exited when I saw the total.

    • Jennifer
      November 20, 2020 / 10:14 am

      There are a few Talbots locations across Canada if you’re fortunate to have one close to you.

  20. Robin Hillyer-Miles
    November 20, 2020 / 5:52 am

    I have to have color on my lips or I look old, old. I use ColorStay by …. hmm, Revlon? Cover Girl?
    I love ther color of your sweater and scarf.
    I have one plaid skirt that I’ve owned for at least 25 years and that’s it, I think.
    You look great.

  21. Candy
    November 20, 2020 / 5:33 am

    Jennifer, which lipstick stays on longer-the Rosewater or the Jane Iredale? I don’t like to reapply my lipstick all day. I’ve been happy with the Jane Iredale that you suggested last year.

    • Jennifer
      November 20, 2020 / 10:13 am

      That’s a great question! I apply this Jane Iredale in Fascination, every morning, no matter what other colors I plan to wear. Then I apply liner on the outside and followed by my lipstick. I have found this Kosas dries down to a creamy color that stays and stays. I’m quite impressed with it! I might not even need the Jane underneath but habits do hang on:)

  22. Bea
    November 20, 2020 / 4:42 am

    Good morning, Jennifer. Gorgeous outfit today! I must be shopping too much because I immediately knew where the scarf came from (Talbots – my favorite store) and I guessed right about the sweater (Jjill). You hit on something about proportion that I have come to realize. Although I love skinny jeans, others styles like the boot cut balance my large upper half better. Will be stealing this look, for sure! Thank you.

    • Jennifer
      November 20, 2020 / 9:04 am

      That’s exactly what I see with this look…a better balance for me. Steal away:)

  23. Nyla
    November 20, 2020 / 4:25 am

    No nude lipstick!! I have tried many and am over what the experts say. Give me a rose; I need a blue based rose or cherry. No pale washed out for me. I have been known all my life for lipstick; never without it.

    • Jennifer
      November 20, 2020 / 9:03 am

      I’m never without lipstick either but nudes look like I’m not wearing any! Rookie mistake for me🤣

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