Casual Holiday Dress-Winter Fashion

Well, it’s finally here! My 25 Days of Winter Fashion collab with Jo-Lynne begins today! We will both be posting new winter outfits daily (skipping over Thanksgiving weekend and Sundays) so be sure you subscribe to my email so you don’t miss a day.

Today I’m styling a casual holiday dress with a plaid scarf and over the knee boots all from Nordstrom. I love wearing dresses but finding one that’s a good length is often a struggle.

(Make sure you read to the end, we are giving away a $100 Nordstrom gift card.)

Fashion blogger, Cyndi Spivey, styling a casual holiday dress.This Karen Kane dress is a little more expensive but I like the length. It’s also a nice thick material with a little spandex so it doesn’t wrinkle.

My handbag is sold out but it’s Sole Society and I love their handbags. Nordstrom has a great selection of Sole Society handbags.

Fashion blogger, Cyndi Spivey, styling a casual holiday dress.The dress comes in several different colors…black, brown, burgundy and a pretty red.

Fashion blogger, Cyndi Spivey, styling a casual holiday dress.I purchased these over the knee boots during the Nordstrom Anniversary sale but I’m happy to say they are on sale again! I like these because they are over the knee, but not extreme.

They come in three different colors but I’m wearing the sandstone suede. If you want a lower heel, these are a good option.

Fashion blogger, Cyndi Spivey, styling a casual holiday dress. Fashion blogger, Cyndi Spivey, styling a casual holiday dress.I purchased these earrings because they are smaller and work well when I’m wearing a scarf.

This will be great to wear to church or to some of my holiday get togethers. The dress would look great with a leopard print scarf and black booties.

Fashion blogger, Cyndi Spivey, styling a casual holiday dress.

What I’m Wearing

‘Maggie’ Three Quarter Sleeve Trapeze Dress (I’m wearing a small)//Over the Knee Boot (Sandstone)//Plaid Infinity Scarf//Earrings//Watch (similar here)//Bracelet

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One of the many reasons I love shopping at Nordstrom is because they have free shipping and free shipping on returns.

Win A $100 Nordstrom Gift Card!

To celebrate the kick-off of 25 Days of Winter Fashion, Jo-Lynne and I are giving away a $100 gift card to Nordstrom! Use the Rafflecopter Widget below to enter. A winner will be randomly selected on 11/23/16 and notified by email. Good luck!

a Rafflecopter giveaway

Be sure to visit Jo-Lynne and see the winter outfit she’s styling today!

I’m so honored that you have taken time out of your day to stop by my blog. If you don’t want to miss a post, you can sign up to receive my daily emails and you’ll never miss a thing. I’m also on FacebookPinterest and my favorite one, Instagram.

Beauty For the Heart~~Here’s the deal: God wants everything you have got. Uncontested priority. Every egg in one basket. All your weight on one limb. This very moment He has His fingers gripped on your chin saying “Right here, Child. Look right here. Don’t look right or left. Stare straight into My face. I am your Deliverer. There is none like Me.” -Beth Moore

In your presence there is fullness of joy; at your right hand are pleasures forevermore. Psalm 16:11

Have a blessed day!

This post contains affiliate links. For more information on what that means, see my About Page: Blog Compensation and Disclosure.

Thank you to Nordstrom for sponsoring this post. All opinions are my own.

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  1. The infinity scarf is lovely! They are such a great accessory with both jeans and dresses. Love the holiday color choices!

  2. I have two weddings this fall/winter and would love to see a ‘dressy dress’ styled. I’m having a hard time finding something to wear!!

  3. I love the boots!! I am always excited for cool weather to arrive so I can start wearing my boots! Thanks for the contest and the chance to win!!!!!

  4. Love the new plaid scarves that are out this season! I have a dress similar to this in a few different colors, very comfortable!

  5. I love this outfit! Perfect for the warm fall we are having. Thank you for always providing great fashion and beauty ideas and, more important, personal inspiration. Have a wonderful Thanksgiving.

  6. I’m 5’8″ so finding dresses and skirts that are blow the knee, but not maxi, is a challenge. I’d love to see some styles that are blow the knee – even on taller ladies. Thanks!

  7. Love this entire outfit. Looks so comfortable (and forgiving when I enjoy too much Thanksgiving) . Too bad dress in my size is sold out in this color. I do like the red!!!
    I enjoy your Beauty for the Heart.

  8. Yay! I love these series!!

    I have a swing dress or two, but have to be careful of the fullness…sometimes they are a little too much. Yours looks great on you…especially love your soft tan boots.

  9. Can you style clothes for when you wear them indoors so we can see what to wear on our feet inside the house. I was brought up not to wear shoes in the house and an outfit looks so different when you don`t wear boots/heels in the house.

  10. Love those boots! I love when you style outfits from the Loft – so I would love to see that in your winter wardrobe series!

  11. I’d love to see you style a nice holiday outfit for a home party, kinda casual but want to look festive and stylish!

  12. Very prudent choice for Thanksgiving dinner! lol I love this color. I’m glad it’s making a come-back. I’m looking forward the winter series!

  13. You mentioned the length of dresses like this can be tricky. I’m wondering if you often wear slip/dress extenders if they are too short?

    1. Hey Terry,
      I’m not a huge fan of extenders. I like the idea! I’m not saying I wouldn’t wear one but with this dress being hi/low, I’m don’t think it would look right.

  14. Beautiful. Boots
    Love the outfit!
    Would like to see how to layer
    for us girls in cold weather!
    It will be here soon!

  15. What color tights or leggings would you wear with this in cold weather? I am sensitive to cold so even the slightest chill in the air makes me cover up every inch I can.

  16. Cute outfit..I’m still on the fence about over the knee boots but I really like yours..
    Have a wonderful day..

  17. I also love the dress that you are styling! I do not have a Nordstrom store near me or a Macy’s either, but wanted to share that earlier this fall I purchased 2 very similar styled dresses from Old Navy & Kohls. I purchased the one from Old Navy for a steal of only $8.00 & it’s one of my very favorites! I am new to your blog and look forward to reading it each day!

  18. Good morning, I love the boots with this outfit. I’m trying to get the nerve to come out of my box and wear over the knee boots. Pray for me! Love, love, love your daily emails. I have gotten all the women in my office signed up for your emails. God is using you my dear!

  19. Love the dress. Easy outfit idea and looks beautiful. My issue is that I work from home. Love my job and love working from home although I miss my coworkers/friends. BUT…I end up throwing together sweats and a shirt or sweatshirt…Love seeing your dressy and casual styles.

  20. Hi Cyndi! Thanks for being a classy Christian lady! Even though I’m a mom of 9(5 still at home,) I like to look nice on a very tight budget. I got to thinking about all the precious ladies out there that have no money to look nice at all. I had an idea, what if we ladies bought one extra thing this season to donate. I’m sure the precious ladies in the shelters would appreciate this so much! Blessings!!

  21. I love the Karen Kane dress with the scarf and love that you give options with low heals. I live in CA and would love to see a dress style with layers and flats. We have warmer temps in the winter and layers are essential. Thanks!

  22. Pretty dress; you wear it well. As for things to style….. How about comfortable clothes/ shoes to wear Christmas shopping and something attractive to wear outside during frigid weather!

    1. I’m 5’10” and ordered a similar style dress from Old Navy in a tall size. I wore it last Sunday with a scarf as well. I wore leggings and short boots.

  23. I enjoy your blog and always read the Beauty for the Heart part! I would like to see some dressy pants outfits for the holiday season.

  24. I love your blog! Love to win the gift card-unfortunately we don’t have a Nordstrom where I live, so it’s online for me!!

  25. THanks for all of the ideas you share for how to dress at out age. I appreciate that you are stylish, chic, and keep all of us up to date on the latest styles. Your “Beauty for the Heart” each day is an added bonus that helps me to begin my day.


  26. You have a lovely ability to put things together and look classic. Thank you for sharing your talents with us.May God Bless you and your family.

  27. Excited to see the 25 days of Winter Fashion….I think I may have to order those boots in black… I would love to see either the black sleeveless blazer or black blazer in how to dress up the look for the holidays.

  28. Very nice outfit Cyndi! I’m glad to see that it’s okay to let our natural skin show on our legs during the colder months. The only dressy holiday event we’ve attended in years is our granddaughters Nutcracker performance that the ballet school puts on. Unfortunately, we will miss it this year, with her being a senior, due to Larry’s chemotherapy.

    Have a blessed day!

  29. I am looking forward to all the post. My challenges are I’m needing new skirts and sweaters hope to see some of them on the blog. Blessings

  30. Good morning Cyndi! I love the dress and scarf. I am so short it is hard to find dresses that fit me correctly. Same with the over the knee boots. Glad Nordstrom carries petites! Would love to win the gift card

  31. This is a great dress and those boots are beautiful! I’m looking forward to the next 24 days. I love today’s Beauty for the Heart.

  32. Love this outfit! I love dresses too, but not a lot are made age appropriate for me… As my mom got older (she’s 92 now) and I began shopping for her, I found it so discouraging trying to find dresses suitable for her…something that wasn’t cut too low,had some sleeves, and was a good length. Now that I’m getting older (63), I’m having the same issues. Thank you, Cyndi for shedding light on some very real challenges for today’s women who want to dress modestly yet still be in style!

  33. I love seeing your styles for fashion over 40 something. When we get in mid 40’s and 50’s sometimes fashion is hard to figure out. Love reading your posts!

  34. so excited about this series…the dress looks super cute on you-I have an apple shape, so I don’t think it would look very good on me.:(

  35. I like the complete look of your outfit. What a nice way to start off your first 25 days of winter fashion. I am looking forward to the next 24 more days. ~Lisa~

  36. Looking gorgeous as always! I have a sweater dress this same color and a plaid scarf so thanks for the outfit idea!

  37. Love love love it!!!! I wonder if leggings would be too much?? I have the worlds ugliest legs!!! LOL You look beautiful as always!!!

  38. Love this green color on you. You always look so beautiful! Hope you and your family have a blessed early Thanksgiving this weekend.

  39. This dress looks adorable on you – both elegant and youthful/playful. And I love the way you’ve tied the whole look together. I think my biggest current style challenge is finding a way to layer and bring in fall-winter colors, textures and patterns, while still creating an outfit that can handle the ongoing unseasonably warm temps so many of us are experiencing. Our nights and mornings here in Southeast New Mexico have gotten quite chilly – just above or below 40 degrees – while our days are still climbing into the high 70’s. So layering properly so that my stripped-down afternoon-version of my OOTD still has a fall-winter feel and visual interest continues to be tricky. Thank you for your wonderful content. I really appreciate your spirit, your message, and all your extremely useful tips! Happy Holidays <3

  40. Love this outfit! I may have to order this dress today! Looking forward to your winter styles–always inspiring & in good taste. Totally my kind of taste–nothing low cut or too revealing!!

  41. Great outfit to kick off days of fashion with such a versatile dress! Thanks for looking out for petite gals and boots complete the look. Now to go check out Jo-Lynne! Look forward to next 24 days😀

  42. Thank you for doing this series! I always get great inspiration from your posts. Scarf styling is something I’d like to see.
    Also comfortable & cute lounging outfit that can be worn away from home.

  43. Love this look on you Cyndi! The color is very flattering! Your blog has really inspired me to be more stylish, as well as, bring me closer to the Lord.

  44. I love this scarf! I ordered it after Jo-Lynne styled it. I like that it’s not too heavy and thick, and I love the infinity versus a huge blanket scarf. Looking forward to the rest of your series.

    1. I’m 48, 5’5″, size 6. I asked my 22 yr old daughter if she thought it would be appropriate for me to wear this outfit to church and Thanksgiving dinner. She replied, “NO”. 🙃 Kids…. LOL

  45. Grace and Peace to you,
    I was so excited when I opened my email to see the 25 Days of Winter Fashion started today! Thank you so much for everything you do. The fashion tips have really made me excited to get dressed for work.

  46. Love the outfit! Could you show us how to style the big blanket scarves. They usually end up looking to big on me but maybe I’m not doing it right.

  47. I love dresses too! So easy to slip on and get going and they are a bit more stylish the old pants and a top option!

  48. That dress is a gorgeous color and looks really good on you! Wishing for some cooler weather here in Phoenix so I can break out the boots and scarves. 🙂

  49. Love the outfit. I usually can’t afford Nordstrom but would love to see the outfits you put together. Thanks for the giveaway.

  50. Sweet outfit! I’m curious though if you go to someone’s house and take off your boots, are you wearing pretty socks? I find that tricky in boot weather and bare legs!

  51. So excited to see all the outfits you style in your 25 Days of Winter.

    However, on me – being a little larger, I can’t wear dresses like this – they just make me look 9 months pregnant. LOL. You look GREAT though! The colors are beautiful!

    And tell your daughter … I think this looks great on you and is perfect for church and Thanksgiving dinner. 😉

    Can’t wait to see all the other outfits.

    Blessings …

  52. I really enjoy your blog and look forward to your no-nonsense approach to beauty and looking your best. It truly does start from the inside, and your daily references to scripture are a pleasant way to remind each of us to be our best self.

  53. I loved your Beauty For the Heart post today.
    I love the lyrics from Turn your eyes upon Jesus. ‘Look full in his wonderful face and the things of the world will grow strangly dim in the light of His glory and grace’

    This is so true, keep looking to Jesus!

    Peace and Blessings.

  54. I LOVE this outfit. It’s perfect for the upcoming holidays! I would love for you to style some jeans and short boots and are there any options other than rolling or cuffing jeans? I like that look but sometimes it looks too casual and to be honest, when it get cold in the winter, I don’t want any skin exposed!

    Thank you!

  55. That dress is so cute! I’ve seen it on Pinterest. Nice to see it on a real human! You look adorable as usual.

  56. You look great from head to toe. I’m a scarf person so I really like it. I’m with you don’t really care for winter but do like the clothes. Thank you for sharing today.

  57. I like the over the knee boots! Looks like a trend to try! Brings the coverage a little higher for the leg and will work with various skirt lengths!

  58. Thanks for the modest, beautiful outfits. One small area I would love some help on is how to wear belts right now: width, how to match, on pants, is outside a top or dress still in?, colors, affordable, etc.

  59. I’d like to have some good ideas for work outfits that are a little more formal than business casual. The trend for some years was quite casual, now it is going the other way, but other than a black, taupe or navy suit I feel adrift.

  60. I so look forward to your days/seasons of fashion. I do have trouble with a lot of the styles since I’m 5’2″ and I have to be careful with most everything because it can overwhelm me. I shop most everything you post. Keep em coming. Devotionals always make the day better

  61. I’m so in love with these swing dresses!! I have 2 from Old Navy…. I do like these boots as well, I’m not crazy about the “Over-The-Knee” boots, but I could handle those, they are beautiful! As always, you look amazing!
    Thank you for what you do, it is always encouraging, Beauty for the Heart as well as helping us look our best!
    I never have dressy holiday events, but casual/dressy Christmas Banquet at church at the beginning of Dec.
    Blessings & Happy Thanksgiving!!

  62. I am another person, who is not so sure about the OTK boot craze, but this style might be “ok” for me. I have nothing against the OTK look, just not for me. I am thinking these boots might look great with the dress you had styled with Glamor Farms too.

  63. Thanks for sharing this chance to win with all of us that follow your blog. Love that you share your fashion sense and your beauty for the heart!

  64. What a lovely, rich color. It will be so pretty at Christmas with a pair of heels and some bling. It looks equally as cute with OTK boots and a scarf.
    Thank you for the opportunity to win a gift from Nordstrom. I think it’s a favourite store for all of us.

  65. Your outfit is great! I’m skeptical of the OTK boots, but you seem to pull them off easily. I’m afraid It’ll appear that I’m trying too hard to be trendy. So I appreciate your OTK boot posts, and maybe I’ll be convinced to get some this year.

  66. Love this dress. I’m going to wear that key hole burgundy, brown and mint print dress that you styled a while back. I will wear brown tights and maybe brown or sand colored boots. This outfit is beautiful on you. Thank you so much for doing this blog. I truly enjoy it.

  67. Cyndi, I love your outfit! You make it look so easy to be stylish and comfortable, which is important to me!

  68. I love the dress today and the way you wear those boots makes me want to try them! So glad to see dress ideas as it is always difficult for me to know how to do dresses in winter!

  69. This dress is so pretty on you and it looks like one that could be casual or dressed up with accessories. I tend to have casual holiday events, and a more formal banquet that I attend in January. One thing I do live in a dress is when I can find one I like with pockets.

  70. This outfit is pure perfection! You could dress it up for a holiday party with your black fur-like infinity scarf (I purchased one just like yours after you featured it), and black suede heels (or leopard…).

    I loved your Sunday post, “God Sees The Bigger Picture” and I have to say that it came at the perfect time for me. We just lost our precious Yorkie on Saturday morning suddenly (he had a rare heart problem, but was doing very well on his new meds after seeing a Vet Cardiologist). He must’ve had a heart attack and just stopped breathing. Of course we were and still are devastated, but God does see the bigger picture and that gives me comfort. My vet said that he might’ve had a very painful death and could’ve suffered, so it’s better he went peacefully. He’s with my Dad in Heaven eating all the cookies their hearts desire! Rest in God’s peace my sweet baby Bennie! Cyndi, thank you so much for giving us scriptures and sharing your wisdom.

  71. I love the color of this dress!! Unfortunately, it is not listed as an option anymore. But, I do love the blue also!

  72. Can’t think of any trends that you’re not sharing with us! I would just like to encourage each of us to keep the focus on inner beauty, as you do….then, no matter what you wear or what size you are, God’s love will come shining through and that’s what people will notice! Genuine joy, contentment and beauty! Prov. 31

  73. Cyndi,
    I am just loving your longer hairstyle. It complements you so well! That scarf has been sitting in my cart for a while now…time to hit ‘purchase’!!

  74. Great outfit for the fall weather here in the Chicago western suburbs! Looking forward to more fabulous ideas for the winter to come! You two are always beautiful!

  75. I think the dress looks lovely on you. I enjoy getting my daily emails from you and JoLynne. I was wondering if you have any suggestions for colors I can pair with gray skinny jeans ?

  76. Love the outfit….thanks for sharing. One of you mentioned the blanket scarves being too big. I too have that problem. I found a nice plaid one that was a square 52X52. I folded it diagonal and cut it in half and made 2 scarves…..one for me and one for my daughter, who is even shorter than me. It worked perfect, as the size is much smaller. The cut edge will fray soon, but it doesn’t show, as you roll it under at your neck anyways. Another idea is to go get plaid fabric and make your own. Lots of youtube videos that show you how and even how to make them smaller. I found mine for $9.00 at Ross, so really cheap when I got 2 scarves out of 1. 🙂

  77. I would love to see you style an “outdoorsy” look with maybe a plaid shirt and some great low casual boots. It would also be awesome to see you style J. Jill and their simple casual classic look. Thank you for your constant inspiration and godly example!

  78. Love the boots in that shade! I just got a pair of booties in a similar shade with cutouts. I might want these tall ones as alternative to the black and grey tall boots I wear a lot. Whole outfit is great – but I’ve had to ban myself from buying more scarves. I picked up two more over the weekend and realized I have sooooooo many!

  79. Cindy, over 50 here. Your outfit looks great, but I am always curious when I should wear tights or hose with a dress or when the bare leg is ok with boots in the winter. It’s just now cooling off in Georgia, so is it a temperature thing when it come to legs eat or a fashion thing? Either way, I never know what to wear!

  80. Love all of your fashion inspiration! I also enjoy your daily “Beauty for the Heart”. I would like to see some holiday party outfits styled with dressy black pants.

  81. I’d love to see different ways to style a blanket scarf.

    Love.this dress. I am all about swing dresses right now.

  82. Very cute outfit even tho I’m not crazy about scarves. I bet a long gold pendent necklace would look amazing. I love those boots but am curious, do they irrate or bother your knees. Based on the hight, it looks like they may rub your knees. Very cute!!

  83. I know you don’t have time to look through all these hundreds of comments, but I’ve got to say this is a gorgeous outfit on you. The colors are a perfect match from scarf to boot….. and this is not a bad price for a dress either. I usually pay near this price or over, for a dress. They are a bit more clothing and if you consider, it is actually a whole ensemble of two pieces you would be paying for anyway, all in one. I LOVE IT, and you are beautiful styling it also… A VERY good start to, I’m sure will be, a beautiful collection, with pieces I must have!! LOL 🙂 I’m getting bolder, never did like swing dresses or clothing and now look at me, I want this one!! I LOVE the earthy color too. My favorite.

  84. I have been waiting for this series and yesterday for some reason I didn’t receive your email. I found it today and wanted to tell you this outfit is lovely. I read you and JoLynne every morning to start my day. I get such good information and I love seeing what each of you style.

  85. Loved your Beauty for the Heart today. Needed those words of encouragement. Cute outfit. I’m so happy I found your blog!

  86. My current challenge is to use the clothes I already have, but wear them in a different way. I am committed to paying off some debt we have, so I am trying not to spend money if I don’t have to!

  87. You have such good taste in fashion! My fashion dilemma: I still like to wear blazers, but I”m having trouble finding the right color, shape, length, etc. Also, a “trend” I would like to see featured is “How to Shop Your Closet” and/or “How to Shop a Thrift Store.”

  88. This outfit smashing on you! I have a similar dress and I own the scarf – it is a wardrobe workhorse. Boots are gorgeous, may have to place an order for them. They put the outfit over the top! Thanks for sharing!

  89. I love Nordstrom too! The dress is so cute. I’m going to look at it and may order it. Thanks for a great post and a great giveaway.

  90. You look great in this dress but, unfortunately, I always look like a small whale when I wear this style!!! Looking forward to all your winter outfits. I much prefer winter clothes to summer. Love all the comfy sweaters and, of course, BOOTS!

  91. Love your blog and your so adorable and encouraging. I look so forward to your postings everyday. Im in search for a great pair of tan or cognac tall boots and the ones your wearing look like the pair I might just have to purchase! Hope they Are as comfy as cute. Happy Thanksgiving to you snd your family.

  92. Thank you, Cyndi! I appreciate the giveaway. Nordstrom is my favorite place to shop.
    And the dress you are wearing on today’s post – va va voom!!

  93. I love the swing dress trend and love seeing how you style them to give me inspiration! Thanks for the give away. You and Jo Lynne are my two favorites to watch

  94. I definitely need a cute plaid scarf now! I am short and really curvy so I think this dress would make me look frumpy. I stick to more body fitting styles. Love the boots!

  95. I’m a fairly new reader and can’t begin to express how much I enjoy your (and Lo-Lynne’s) blog. I look forward to all the posts!

  96. I want to thank you–Cyndi and Jo-Lynne for keeping our little group on trend and up-to-date on all things fashion. Not everything appeals to us older ladies, but you help us stay current and relevant. Although some of the things are pricey, I can adapt to lower price points that I can find. Love being a part of this group.