Plaid Trend: Wear Now And Later

Happy Friday, ladies! Today I’m teaming up with Jo-Lynne Shane again to share Fall Trends: Now & Later! We are styling a fall trend two ways every Friday during September, and this week we’re styling the plaid trend.

I picked up this plaid boyfriend blazer at Old Navy. This soft blazer can easily be worn now in early fall, but when colder weather gets here, I can add a sweater or a turtleneck.

I decided to style a casual weekend look with a white t-shirt and sneakers.

This white t-shirt is from EVEREVE, and it’s on sale. It’s the tee I keep grabbing because of the fit, and it’s not see-through.

This fall, small handbags are still trending, and I carry this top handle bag from Sole Society all the time. It also comes in an off-white color.

Plaid Blazer (I’m wearing an XS)//Kut From the Kloth High Rise Jeans (I’m wearing a size 4)//White T-shirt (I’m wearing a small)//Sneakers(TTS)//Earrings//Bracelet//Top Handle Bag(on sale!)

Next, for later in the season, I styled my plaid blazer with a sleeveless turtleneck. I also traded in my blue denim for black jeans.

My sleeveless turtleneck is almost sold out, but I found another one at Express here.

Since I’m wearing black jeans, I added my Vince Camuto black heels. Target has a less expensive option here that would look great.

Plaid Blazer (I’m wearing an XS)//Black Jeans (I’m wearing a size 4, another option here)//Black Sleeveless Turtleneck (I’m wearing a small, similar option here)Vince Camuto Heels (less expensive option here)//Earrings//Bracelet

It’s easy to add plaid into your fall wardrobe with a plaid blazer!

Be sure to visit Jo-Lynne and see how she’s styling plaid for now and later!

Thank you for taking the time out of your day to stop by my blog. I’m also on FacebookPinterest, and, Instagram.

Beauty For the Heart~~While I don’t have this Christian life figured out and the Lord knows I need constant reminders. Like the reminder in 1 John chapter 3 that I am to LOVE. And I don’t think it means to love only those who are loveable. We are to love those who have hurt us, those who persecute us, and even those who are different from us.

The beautiful message you’ve heard right from the start is that we should walk in self-sacrificing LOVE toward one another. 1 John 3:11

So these are his commands: that we continually place our trust in the name of his Son, Jesus Christ, and that we keep LOVING one another, just as he has commanded us. 1 John 3:23

Who do you need to show love to today?

Have a blessed day!


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  1. The dress you shared in your email has been in my cart for awhile…I finally pulled the trigger on it, can’t wait to see how it looks on you! I don’t have a fall wedding but going on a cruise to Bermuda in October and plan on wearing it for that!

  2. I’m interested in the trend of wearing tennis shoes with skirts or dresses. I spent 6 weeks in Poland this summer for a mission trip and many women of all ages wore tennis shoes with dresses. They looked so chic.

  3. Yes, please style a skirt with sneakers! Some of us have foot problems that necessitate wearing them instead of other shoes. Thank you for asking!

  4. Love, love, love posts like this. I can’t always picture how I can wear an item more than one way. Thank you!
    Also love your dress for the wedding!


  5. Yes, share the skirt with the sneakers. I wear casual skirts in the summer with sneakers or casual sandals.

    Love the plaid jacket. Just bought a few blazers for the fall.

  6. Love the now and later post!
    I actually have worn sneakers with a casual skirt, but they were kinda streamlined lightweight sneakers. I see younger gals wearing heavy “Dad sneakers” w/dresses, but I think that would just look frumpy on older women.

  7. This blazer is super cute – and I love it both ways! Interested in the sneaker with skirt look – likely would NEVER wear it, but interested in seeing how you put it together.
    Have a great weekend!!

  8. Loved the blazer. Yes, share skirt with sneakers, especially with a graphic tee. That’s a look I like but can’t figure out.

  9. I love both blazer looks-super cute and classy-even with tennies! Your wedding dress will be gorgeous on you! I have always felt the skirt with sneakers is a little young, but you make everything look great, so I’d be interested to see it…LOVE to you. Speaking of love, my son has begun working at a company called Preemptive Love part time while getting his masters. He’s in Nashville and the company is amazing. You may want to read the book Preemptive Love-it certainly opened my heart to others! Much love to you for all you do!

  10. Would definitely love to see your style in sneakers and dresses/skirts. I’ve worn sneakers before with t-shirt dresses and floral swing dresses, but would love to see your take on the trend.

  11. Yes, please share the skirt with sneakers! Also, what sneakers are you wearing in this pic or where did you get them? Thank you for the beauty for the heart today! I so needed it.

  12. Cyndi—I love the Old Navy plaid blazer, but the sleeves on the model in the Old Navy ad are kind of large and a little baggy-looking. I like blazer sleeves to be close-fitting, like the one you have on. Did you have the sleeves tailored? I may order the jacket and if I don’t like the fit of the sleeves, I can always take it back. Just wondering. Thank you!!

  13. It’s surprising how a blazer can dress up any look and make it look classy.
    I’ve never worn a dress with runners but I would like to see how you pull it off. I like the look on others but have never worn that look myself.

  14. I love wearing my Converse with my casual dresses and skirts, and I’ll also wear my van slip ons And yes I’ve worn a graphic T with a skirt, usually denim. In Colorado, casual style is the way to go so it’s a much much more accepted trend than in other parts of the country. You should totally try it!

  15. I have been wearing sneakers and dresses/skirts for some time now – if one wears it confidently, they can pull it off…my sneakers are Golden Goose and although I’m not thirty-something anymore, I love them and don’t really care what others think…wear what you love!

    Regarding your blazer, I live in them in the fall. I much prefer a tailored look so I don’t wear it as long and boxy…just my preference.

    Lol..I read your blog on my phone and every time I read the comments section, I accidentally press the “reply” button. I don’t know how many times I have responded to other’s comments. Maybe it’s just me…

  16. Hi Cyndi it’s nice to hear from you today.. was there a post yesterday and I missed it? Love these looks with the blazer and I would absolutely love to see how you would style sneakers and a skirt plus I’m a sucker for a graphic tee. I’ve seen this look done on the younger bloggers but thought it might be out of age range for me at 51; however I do wear my converse with t shirt dresses in the spring so why not a skirt? Have a great time at the wedding the dress you’ve chose is gorgeous and I’d like to see pics of you wearing it.
    Karen ❤️

    1. Also Cyndi could you please show the top handbags we should have for fall? And maybe which handbag you would pair with a certain outfit? Whether it be casual or dressy , or casual going up a notch by adding the right handbag.

  17. A big NO to sneakers with skirts. I know it is just in my head but it reminds me of an old woman with bad feet. I think it looks great on young girls but not on us over 40 crowd. Sorry I just do not like it. I do love this blazer though. Perfect for fall and winter wear.

  18. You look fabulous,as always. What a great way to wear the plaid trend.
    P.S. I would be very interested in seeing yoi style sneakers with a skirt. I like trying trends, and it’s very helpful to see them worn by someone whise style I admire (that would be you 😊)

  19. now this is my sort of plaid.
    Did you have a bewsletter yesterday ? I did several searches throughout the day and never found one Perhaps it is like in the past and i will receive it in 3-4 days.

  20. I live here in FLA and we wear sneakers with skirts and dresses a lot, it is considered our dress shoe cause its not a flip flop 🙂 I love the now and then looks. Keep on styling

  21. HI Cyndi! Such a timely question about wearing tennis shoes with skirts and dresses!! I have plantar fasciitis BAD!! I just received custom orthotics and the podiatrist wants me to wear my running shoes to work every day for 2 months. Ugh!! I would LOVE to see you style tennis shoes with dresses!!!! Thoroughly enjoy your blog!

  22. These are great looks. The transition pieces are staples so its an easy switch out. I sometimes wear sneakers w my t shirt dresses or a jersey swing dress. I have also tried sneaker w a full skirt for a 50s vintage look. I would love to see what you have come up with

  23. I would like to see how you would style skirts or dresses with sneakers! I will be traveling to Italy soon and am struggling with needing super comfortable shoes that could work with a skirt and pants/jeans. Your looks are always spot on! And thank you for sharing your faith.

  24. I think the lace up sneaker with skirts and dresses looks a little too youthful. Yet, the slip on sneakers seem to work (for me). I usually wear a Tom’s slip on and it’s a pretty cute look.

    1. Love that plaid old Navy Blazer it’s so fun with the t-shirts and sneakers. It reminds me so much of I jacket in had in my 20’s.

  25. Slip on sneakers with a skirt or dress would be a fun look. Would love to see how you put your special flair on it! Enjoy your time at the wedding.