Plaid Shirt OBSESSION: Four Outfits to Try Now

Happy hump day, pretties!  I finally got my closet transitioned over from summer to fall/winter last week.  Even though it’s a lot of work, I love it for a few reasons. First off, I get to clean out and organize everything.  Before I swap out clothes for the season, I remove anything that I didn’t wear all season long and put it in a bag marked “clothing purgatory”.  It goes into the attic until next year and then I decide if I like it enough to pull it back out again.

The second reason I love my seasonal closet clean out is that I get to pull all of last year’s clothes out of storage and put them back in my closet. It’s like meeting up with old friends!  I see all of the pieces I’ve loved and missed for the past year.

One of those old best friends is my plaid shirt which you saw a lot of last year. When I pulled it out, I couldn’t wait to introduce it to some new friends in my closet from the Fall 2017 GYPO Style Challenge – like my new beige cardigan and suede loafers.  And of course, Mr. Plaid Shirt pairs perfectly with lots of his old friends too.

Here are four NEW ways that I’m pairing up my plaid shirt this fall. My original plaid shirt is sold out but I’ve linked a similar one here, here, here and here. I shopped my closet for all of these outfits but linked up exact pieces where I could.

Beige Cardigan + Plaid Shirt + Distressed Jeans + Loafers

The plaid shirt goes preppy when paired up with a boyfriend cardigan, suede loafers and a cross body bag. Distressed jeans lend a little edge to the preppy-ness.

Get the Look


Plaid Shirt + Graphic Tee + Frayed Hem Jeans + Ankle Boots

I adore a good graphic tee layered under a plaid shirt!  Finish it out with my favorite SUPER SOFT frayed hem skinny jeans, these comfy low heeled taupe ankle booties and a leopard clutchTip:  Pin this one, it would make a GREAT Thanksgiving outfit with a “Thankful” tee layered under the plaid shirt!

Get the Look

Plaid Shirt + Striped Shirt + Black Jeans + Leopard Flats

Layer a striped long sleeved tee under your plaid shirt and pair it with black jeans (this pair is pricey but super flattering, these are budget friendly) and leopard flats for an everyday look that’s comfy and works for everything.

Get the Look


Gray Cardigan + Plaid Shirt + Winter White Cords + Riding Boots

Tuck your plaid shirt into these winter white cords, add a leopard belt and layer on a gray cardiganRiding boots finish it out and give it polish.

Get the Look

It’s Your Turn:  What’s your favorite way to pair up this fall/winter staple?

Getting my pretty on with Sheaffer Told Me To and The Pleated Poppy.

I Feel Pretty Link Up

It’s the day of the week at GYPO where we celebrate what makes us feel pretty. Whether it’s a new outfit, hairstyle, or makeup, the I Feel Pretty link up is about anything and everything that makes your life prettier. Even if you’re not a blogger, you can still play along. Just tell me what made you feel pretty this week in the comments.

There are just a few simple rules:

1. Follow GYPO. (Bloglovin‘, FacebookInstagram or Pinterest)
2. Link up your pretty post.
3. Link back to GYPO.
4. Visit other pretties.




  1. Laura

    Great outfit inspiration! I love the graphic tee and plaid!

    • Alison @ Get Your Pretty On

      I agree. Love it too! It seems it never gets old. Hope you have a great weekend traveling! 🙂

  2. GlamorousandGeeky

    love the color of that plaid shirt! I have a similar plaid top and love it!!!!

    • Alison @ Get Your Pretty On

      Me too! Still loving that green plaid. Looking forward to cooler weather to be able to wear more jackets. 🙂

  3. Cheryl Maday

    I love the plaid with your Stella & Dot bag in the first shot! 😉 Thanks for hosting the linkup!
    Cheryl Shops |

  4. ADA

    I have the shirtdress version of that shirt (as a long-sleeve dress) and I love it. You created many great Fall looks here. Love them, Alison.

    Welcome by tomorrow and join my linkup. =)

  5. Sheila Charbonneau

    I ordered the JCrew shirt and am desperate for it to get in my hands! Which is a little ridiculous because it’s 100 degrees in So Cal right now, oh, well. I still can’t wait 🙂

  6. Lanae Bond

    Great looks! I love the second on the most because I love print mixing!

  7. Amanda Methvin Harvey

    I bought that same shirt last year. I love all of the looks you shared. I can’t wait to try them. My favorite way to wear it last year was with black jeans, camel colored boots, and a white puffer vest.

  8. Nicole Mölders

    Thanks for linking up to Top of the World Style. great styling suggestions.

  9. Lata Martinez

    Hey! You have a lovely collection of clothing. I will definitely try these four outfits. I love to wear a Long cardigan with loafers. I want to add lingeries to this then it will be perfect for me.


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