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Wear Now and Wear Later Plaid Blazer Outfits

February 17, 2022

As we approach a new season I can get a little ahead of myself. I liken it to going through a buffet line when I haven’t eaten all day. Sometimes I overload my plate and discover my appetite was bigger than my stomach. I get similar frustrating results if I start shopping for the new season too soon. I end up with a plethora of bits and pieces and no clear direction. So at this time of year I limit myself to strategic shopping, buying only pieces that I can fit into my wardrobe seamlessly. Thus I have pieces like this great plaid blazer that I can wear now and later.

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Styling a Plaid Blazer Now

Plaid Blazer for Now & Later

If you’ve been a Dressed for My Day reader for long, you probably know these two things about me. One, I love blazers. And I don’t just love them in theory; I really wear them often, even in my casual lifestyle. In fact, I’d much prefer to wear blazers over jeans than dress pants or a dress or skirt.

And two, since I like to wear them so much and generally keep my blazers in my closet for years upon years, I don’t mind investing in quality jackets. I do have some less expensive blazers in my wardrobe, too. But when it comes to these jackets I’ve found you do indeed get what you pay for. And I want my blazers to fit well, feature great fabric and have nice stitching.

How to Style this Plaid Blazer Now
similar v-neck sweater

So this Reiss Essie Glen plaid blazer is quite pricey. But I’ve rounded up a slew of other lovely plaid blazers at a full range of price points and gathered them in the shopping widget below. This post is not so much about this plaid blazer I’m wearing, as it is about styling any plaid blazer now and later. (By the way, the Reiss Essie Glen plaid blazer was in fact temporarily marked down substantially when I purchased it. I never pay full price for anything!)

Distressed Jeans and Booties

Right now I’m wearing my plaid blazer over a lightweight sweater (similar), this camisole and my lightly distressed jeans. I kept the coloring soft and the intensity level consistently low in this outfit to help pull it together. I added a pretty silk square scarf for a little warmth and added interest. I love contrasting a print scarf with a plaid blazer!

Styling a Plaid Blazer Now

I finished off the look with gold split hoop earrings, stylish sunglasses (similar frames//more economical) and my taupe suede booties (similar). I love how a plaid blazer adds texture and interest to an outfit like this. Of course any blazer adds a bit of structure to an outfit (even if it’s an oversized blazer), elevating the style quotient significantly. But a plaid blazer just looks so fresh, a little more casual and a bit more colorful.

Styling a Plaid Blazer Later

Choose your plaid blazer wisely and you’ll be able to wear it year round. I think most of the ones I included in the widget above will work in at least two seasons, maybe more. So let’s see how I switched things up a bit to style my plaid blazer for later when the weather warms a bit.

Styling a Plaid Blazer Later

I guess the main thing I did here is swap out the cashmere sweater for a simple sun-faded navy v-neck tee (TTS). Mine is a short sleeved t-shirt, but you could wear anything from a long sleeve tee to a tank top with the same effect. I had really wanted to pair a lighter blue tee with this plaid jacket. But the good thing about plaids is that they usually have a number of colors in them from which to pull for things like tops, scarves and shoes.


I replaced the neck scarf with my two-tone pendant necklace to lighten things up a bit, but I still wore those split hoop earrings. And I’m pretty sure I saw my Nordgreen Native watch peeking out from under my rolled up jacket sleeve. (Use code KAYHRMS for 15% off your purchase at Nordgreen)

Scarf and Shoulder Bag

But I tied that pretty floral print scarf to the strap of my shoulder bag for interest and handy availability. Little details like that can really set your outfit apart and elevate your style.

Now I know that these retro trainers tend to polarize readers. You either “get them” or you don’t. And I understand. There are some trends that I just don’t “get” either, hahaha! But I’ve seen so many stylish women – in pictures and in real life – who have created such great juxtaposition wearing similar retro trainers with a blazer. It’s definitely “a thing.” And I’m all in!

Wearing Retro Trainers with a Blazer

I actually had this pair of flats in the car that I had planned to show as an option with this outfit. And you absolutely could create a great look with them. But, as you can see with the snow and salt on the ground, it was ridiculously cold when we were snapping these photos and I just couldn’t bear to bare my ankles!

Styling a Plaid Blazer for Spring

I really love the way this outfit came together, too. And I can’t wait to wear this sporty combination this spring when it warms up a bit. This is the kind of outfit I’d definitely wear to lunch with friends, out and about shopping, to a museum with my husband or for a day of tending to wedding details with Abby.

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You can shop the look through the links in the copy above or through the shopping widget below. Sale prices are not always reflected in the widget, so click through to get pricing info. Remember, if you purchase anything through these links I potentially earn a commission, but at no cost to you. Thank you for shopping through Dressed for My Day. I am grateful!

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Blessed for My Day

Writing about a plaid blazer reminded me of Joseph’s multi-colored robe or coat, given to him by his doting father. Playing favorites is no laughing matter. When we choose favorites among our friends, our grandchildren, our pastoral staff or our siblings we create undesirable strife, resentment and frustration among them. We play with people’s emotions and set them, including “the favorite,” up for hurt and mistrust.

But let’s be honest. Sometimes one person among the group just “fits” us better. Maybe they’re easier for us to get along with, more fun to be with, friendlier, more charismatic and charming or just more like us. How can we resist treating that person a little differently? Right? We can ask God to help us treat them and the others the way He does. We can seek to see each person through His gracious and good eyes. And we can lavish our affection on Him rather than any one person.

Now Israel loved Joseph more than any other of his sons, because he was the son of his old age. And he made him a robe of many colors. But when his brothers saw that their father loved him more than all his brothers, they hated him and could not speak peacefully to him. ~ Genesis 37:3-4

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xoxo, Kay
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15 thoughts on “Wear Now and Wear Later Plaid Blazer Outfits

  1. Good Morning Kay…..what a great way to “dress up” a pair of jeans. I have seen this and I like it as well. I think the scarf give it more of a feminine look with the blazer which I also like.

    Have so much fun on your trip to FL. We left OH and raised our girls there and lived over 20 years. Looking forward to following you along you trip!


  2. Love the blazer and jeans look. Question. The link for the “Mother” jeans doesn’t appear to look like the same pair you have on….yours appear longer and the ones noted on the link look short and wide legged at the ankle. Could you double check? Love your blog and instagram!!!! You must be going to St. Augustine for one of your stops! Such a beautiful town!!!

  3. I LOVE these outfits! The first one is my favorite. I’m short so I have a couple blazers, but I think I look better in short jackets. I’m amazed at how good the scarf looks with it-I never would have thought of that.
    I really liked the video yesterday-very helpful. I’m sorry about your white skirt. I found that ink stains come out like magic with aerosol hair spray! Of all things!
    How nice of your husband to plan a trip like that! I hope you both have a great time!

  4. I love the colour of your blazer. I have a similar one in black and white with a green line that I have had for many years. I love to wear it with jeans, but I sometimes wear it with black trousers if I want a more dressy look. In cold weather, I throw a black ruana over the top. It’s cosy and I like the way it looks. That’s the great thing about plaid blazers – they are so versatile and, if you get a classic cut, they never go out of style. Here in south west England we don’t get the extremes of temperature you get in parts of the USA, so I can wear mine pretty much year round.

  5. Perfect timing for this article, I have a brown plaid blazer, very similar hanging in my closet, not yet worn, and was concerned it was going to spend a long time hanging. Love the 2 looks with the blazer, and the lighter wash jeans. Have a safe and fun vacation!

  6. You’ll love St Augustine. Very charming old city in Florida! Thanks for the blessing. I was struggling with how to treat a friend and this helped. I have several old blazers still in my closet from when I was working. I think I’ll drag them out and see what I can do with them. Thanks for this post and have a lovely vacation here in sunny Florida!!

  7. Love your looks with the blazer, except the distressed jeans. Not my thing. I have a blazer I bought from Talbots last fall with gold buttons on the sleeves that I love that would work nicely too, Liked the BFMD.
    I bet you are excited for your trip. Have fun, I must hurry and get ready for Women’s Bible study this morning. Have a blessed day.

  8. Very pretty. I especially like the blazer with the blue sweater. Adds more color to your beautiful face. Have a wonderful day.

  9. Enjoyed the post and the look! Blazers look better on me than cardigans. Kay, I would love to hear more about how you wear the sleeves on your jacket: to roll up, to fold up, or not? To do special roll and then 1/2 roll again? To turn part of the rolled cuff down like Talbot’s “artfully casual” style? What is currently trending? How and why do you style your sleeves? Thank you!

  10. Hello Kay. Have a great vacation. I think it is so wonderful that your husband has done all the planning.

    Your post today hits close to home. I too like nothing better than wearing jeans that are comfortable and really fit well with a blouse, sweater or T-shirt and a blazer. I love blazers for their comfort and versatility.

    I noticed the sleeves on you blazer are rolled up. Is the roll up a fashion trend now? I am a petite and because many blazer sleeves are often a little too long I have been known to do a roll up too. I have always wondered though if in doing that I am compromising being stylish. What do you think? On you this looked great.

  11. Kay,
    Your blazers are great. The smaller plaids are versatile with thin lines of color that could be worn with so many different tops. Your blue choice is a good contrast.
    Sneakers? I’m still “on the fence”so to speak. The comfort is appealing and looks good on you and others I see.
    Wishing you a happy and safe trip. Enjoy!

  12. Hi Kay,
    I am a real fan of blazers. I checked out the one you are wearing here and it is out of my size…Do you know if that particular pattern and color will be back in again soon? I liked several of the others that you gave us links for. Most do not have size Large that I need, so do you expect any re-supplying at these sites?
    I also hope you all have a safe and happy vacation. It sounds like you’ve earned it, so I hope you enjoy the time away.
    God bless.

    1. Hi Jane. I really don’t know no checked the Reiss website but they have the same few sizes. I’m not real familiar with the brand and I think they’re kinda new at Nordstrom so we’ll have to wait and see. Fingers crossed!