September 29, 2014 - Easy Outfits, Style, Trend Watch

Three Ways to Wear a Plaid Shirt


I was going to title this post “How to Wear a Plaid Shirt Without Looking Like a Lumberjack, the Brawny Paper Towel Guy or a 90’s Grunge Rocker”, but I didn’t, for obvious reasons.

However, the sentiment is the same.

You can style plaid shirts without being one bit brawny or grungy.  Plaid shirts are totally on trend for fall and winter.  They’re also completely wearable (and dare I say, chic?) when paired up properly.

Here are three of my favorite ways to pair up plaid shirts.

1.  Plaid Shirt + Sweater

Plaid shirt layered under a sweater.  #plaid #shirt #outfit #sweater

2.  Plaid Shirt + Puffer Vest

fall outfit - plaid shirt, vest, skinny jeans, riding boots

3.  Plaid Shirt + Military Jacket



I’m wearing this blouse in the photo above.

 [Plaid Henley]

[Plaid Popover]

[Plaid Button Down]

[Plaid Tunic]

Fall FB Cover Graphic White Learn More

Are you looking for even more ways to style a plaid shirt?  Then you’re in luck!  A plaid shirt is one of the items on the wardrobe basics shopping list for the Fall Style Me Pretty Challenge.  You’ll get a shopping list of fall pieces plus 21 days of outfits created from those pieces.  Here’s an example of one of them.

Fall Sample Outfit 3

Regular registration closes on Thursday, October 2nd.  Sign up HERE for the best rate!

It’s Your Turn:  Are you into plaid shirts or is this a trend you’ll be skipping?  Tell me in the comments.

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Get your free Closet Staples Casual Capsule Wardrobe shopping list + four free outfit ideas!

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  • I did a similar post recently I just love a good plaid shirt, well done!


    • Great minds think alike! Plaid shirts are my favorite! 🙂

  • A plaid shirt can be so versatile for fall layering under sweatshirts, vests and jackets. A perfect piece of a casual look. Great styling tips!
    Red Reticule

  • All three looks are perfection, I just love plaid this time of year!

    • It’s so fun styling plaid shirts!

  • I love plaid shirts!!! And I loved the three ways you showed them styled here. Happy Monday!

    • Happy Monday Shay! 🙂

  • LOVE LOVE LOVE a plaid shirt! I’m wearing a blue one in my post today, and today sass it up I paired it with leopard flats. The Brawny paper towel guy would have never done that. 🙂

    • I ran over to your post! Black jeans, plaid shirt, and leopard flats = LOVE LOVE LOVE!

  • I already grabbed a pair at the last LOFT 40% off sale! Yea Me!

    • Yay Karen!! So glad you were able to get it on sale. I love LOFT!

  • I’m a big plaid fan for fall! Great ideas! I hope you’ll stop by my blog this week and enter my Denim Giveaway!
    xoxo –

    • Thank you for the reminder Kate. Can’t wait to see it up!

  • LOVE!! I have so much plaid I needed some inspiration too!
    XO Ellen from Ask Away Advice + Fashion Blog

    • I love pairing plaid for fall and a little inspiration is always nice. 🙂

  • KellyinPA

    I do not own a plaid shirt but plan on purchasing one to do the Fall Challenge. Looking forward to Friday!

    • I’m so excited and can’t wait for everyone to start the fall challenge.

  • Laura Watkins Ryner

    Can’t wait for Friday. I’ve been pre-challenge buying, so hopefully I’m ready.

    I still need vest options, since a puffer vest isn’t too practical in my classroom.

    I have a fantastic blue ON plaid shirt. Can’t wait.


    • I love it Laura!! Hope you have been enjoying your shopping for the fall challenge!

  • maria

    can you let us know where the plaid shirt that you paired with the grey pants and white vest is from? is that a long sleeved gray shirt underneath or is it part of the plaid shirt. LOVE, LOVE LOVE your style!

  • I ADORE plaid shirts and have a handful of them in my closet. Can’t wait to break ’em out soon!

    • I would love to see how you pair them Ashley! 🙂

  • I love plaid shirts – they are so fall! Thanks for the styling suggestions!

    • I love fall Lana! Can you tell? 😉

  • Suebee23

    Alison, I love the plaid shirt look, but never seem to pull it off right. If I leave it tucked out it looks too long and boxy on me. How can I get that fitted look?

    • Have you tried different types of plaid shirts from other stores before purchasing? The styles vary in length. If you can, try to get one that has the relaxed fit style that would help you get the fitted look. The Target links above would be great!

  • Love this plaid trend! So fun! Thanks for the great ideas:)


    • They are so fun Audrey! You’re welcome.

  • now I just need to find one I like!

    • Shaunacey, you will enjoy looking for the colors that you like! They are everywhere. 🙂

  • hl

    I love plaid but button up shirts are not my friend. I have big boobs and short waisted and have a hard time with finding a good fit. But I love the trend. I can always do a plaid scarf if I really wanted to.

    • Plaid scarfs are great for fall too!

  • I have tons of plaid shirts and love wearing them year round.

    • They are great and easy to throw on, Tracy! 🙂

  • Plaids are my favorite in the fall! Nicely done(: Susan

    • Thanks Susan. They are a great trend and completely wearable. 🙂

  • Saxon

    LOVE these looks! I have several plaid, flannel shirts. I’m looking for one that isn’t flannel. Are any of the links you posted not flannel? 🙂

    • Saxon, the Target links material are 100% cotton. 🙂 Happy shopping!

  • I especially love it under a v neck sweater. It reveals more of the plaid and has a more laid back feel.

    • Yes! Sophisticated lady look!

  • I’m obsessed with plaid this season. Love all three looks here and the more options the better. Thanks for all the ideas! ~Cynthia

    • You’re welcome Cynthia. I’m a little obsessed too!

  • I love all three styles and completely agree! I’ve been having the HARDEST time finding a plaid shirt that fits right… mainly because I’ve been looking at Old Navy and I should know better. Their stuff just doesn’t fit me right sometimes. I’ll be checking out some of your suggestions. I loooooove plaid anything so the fact that I don’t have a plaid shirt is not okay!

    • It can be a little difficult finding the perfect fit, but they are everywhere and you will find it. Happy shopping! 🙂

  • Thanks for sharing this. I don’t own many plaids but want to try it out this season, but was a little clueless as to how to wear it. Pinning for sure.

    Thrifting Diva

    • Enjoy the plaid shirt Ayana! 🙂

  • i m addicted to plaid shirt and love wearing them all year 😛 P/s: you look so pretty on your plaid shirt 😛

    • Thank you! I love wearing plaid shirt all year too! They are comfy and cute!

  • I love checked shirts too Alison & I’m on the hunt for another one! I love them with a jumper & khaki jacket! Ax

    • I love your style! Can’t wait to see it on your blog, Happy shopping!

  • Rebecca

    Hi there Alison. I’m wondering where you got the military jacket in photo 3. I love how it is cinched at the waist and I could really use something like that. All of the ones I’ve come across the past week don’t cinch and I look very boxy.