Three Ways to Style a Plaid Shirt for Fall 2019

Happy Monday Kittens!

Fall is officially here and I couldn’t be happier. Summer has lasted entirely too long in South Carolina, and I was ready  for her to leave and never return…lol!  I’m so excited to wear lots of hats, scarves, sweater dresses, tights, moto jackets, bad ass boots, and of course all of my favorite Fall prints. One of my must-have prints  for Fall is plaid. I honestly don’t even care what type of plaid it is. It can be Tartan, Buffalo, Tattersall,  Windowpane, Gingham, or Houndstooth.

As long as it’s plaid I’m wearing it! In this post I decided to take a plaid shirt and style it three different ways. Plaid is such a versatile print. So I wanted to showcase how you can mix and match your outfits with one plaid shirt.

The “Casual” Plaid LookHow to Style a Plaid shirt for Fall

Crop top(similar)//Plaid Top//Skirt//Hat(Similar)//Boots(similar)

If you’ve been reading this blog for awhile, then you know I have a special place in my heart for crop tops. It can be 100 degrees or 40 degrees outside  if I can find a crop top, I’m going to wearing one. This look is probably one of my go-to looks when the temperature starts to drop. I really think it’s 90’s inspired with the shirt tied around the waist. It’s very reminiscent of the 90’s grunge era without so much of the grunge.

During the week I’m usually super busy, I’m constantly working on something. So I want to make sure that I’m comfortable and fashionable at the same time. This is my idea of a “casual” outfit, I’ve chosen to wear a black crop top turtleneck which I purchased  from Forever 21. A similar version with long sleeves, can be found here. I’ve paired my crop top with a black Sweet Dirt woven flounce skirt. It features; a ruffled hem, elasticized waist, and a concealed back zip closure, and it can be found here. My  red Sweet Dirt allover tartan shirt that’s tied around my waist, can be found here.


I absolutely loooovvvvee hats, like I’m pretty much obsessed with them. So of course all of my  looks feature hats. I purchased this hat from H & M and I actually found it in the kids departments….No Judgements. If you’ve never checked out H &M Kid’s Department for fun and cute accessories you’re definitely missing out…lol!

Besides this hat was made for me, I mean it has lashes on it.  Since I never leave the house without my  lashes. It was a no-brainer that this hat was definitely coming home with me. Fashion doesn’t always have to be serious it can  also be fun.  I’ve found an adult version of my hat with larger pom poms, that can be found here. Fashion should always express who you are and how you feel. Finally, I’m wearing my six inch, yes six inch snakeskin ankle boots from Fashion Nova, a similar pair can be found here.

**Snakeskin is going to be really hot this Fall. So make sure you pick up a little faux snake skin for the Fall/Winter. Of course make sure it’s faux, we don’t want PETA coming for you!**

The “Sophisticated” Plaid Look

Plaid Shirts for Fall Three ways to Style a Plaid Shirt in Fall How to Wear Plaid Shirts in the Fall

Plaid Top//Beret//Skirt//Boots(similar)

For my second look I’m wearing my red Sweet Dirt all over tartan plaid shirt, which can be found here, along with a black Sweet Dirt pencil skirt which can be found here.  I adore wearing pencil skirts because it elongates the body and it adds a real hint of femininity. I chose to tie my plaid shirt in a knot and wear it cropped. However, feel free to tuck your top in,  it’s totally up to you.

In my opinion nothing says sophistication,  like a black high waist pencil skirt. Honestly, when I put on a pencil skirt I instantly feel put together, sexy , and powerful. It’s like I can handle anything life throws my way, because I’m dressed like a legit adult. I mean adulting is hard enough  and I don’t know about you, but if I can wear something that makes it feel easier, I’m wearing it.


For my accessories I’m wearing a  black beret which I purchased from Nordstrom. I mean a pencil skirt and beret, how could you not look put together and fashion forward?  My beret is made of wool felt  and you can find it here. Lastly, I chose a pair of black lace-up boots, because I feel like they added a dramatic flair to the outfit.

My boots are military-inspired and they’re very bold, which is another reason I chose them for this look. A similar version of my boots can be found here. I’m carrying a Betsey Johnson clutch, that I’ve had for awhile. Like I said fashion is all about expressing who you are. I love this look because it’s everything I strive  to be as a  woman in this world; powerful, strong, sexy, and chic. This outfit makes me feel all of those things.

The “Starbuck’s” Plaid Look

How to Wear a Plaid ShirtDifferent Ways to Wear PlaidHow to Wear Plaid in Fall

Plaid Top//Jeans(similar)//Hat(similar)//Boots(similar)

One of my simplest and guiltiest pleasures is going to Starbucks, on a Saturday morning and walking downtown. In the summer it’s too hot to drink coffee and I hate iced coffee. So when the temperatures start to drop I take full advantage, and embrace the downtown atmosphere. It’s such a wonderful time to walk around downtown,  just take a breath, and enjoy the beauty that is life.

I decided to do something completely different with this look and wear jeans. This is the first time that have I worn jeans in years…y’all! Seriously, I cannot remember the last time I wore pants.  I know it sounds crazy, but I love my skirts, shorts, skorts, and dresses.

However, one cannot have a post about wearing a plaid shirt and not incorporate jeans into the look. I’ve paired my all over tartan shirt with a pair of ripped dark jeans. These jeans are dark rinse which I love and they’re ripped which means me feel so amazing!  I bought these jeans from Nordstrom, but a more affordable pair can be found here.


Is it really Fall unless you’re wearing a wide brim hat…of course not! One more thing to love about Fall fashion there are so many hat options hat-wise. A large wide brim floppy hat is always on my list of must-haves. I always feel like a hat takes any outfit from ordinary to extraordinary. A similar version of my hat can be found here.

My  black mini bag, with a cutout handle, is from Charming Charlie’s. It can also be worn as a  cross-body bag, which I love. So here it is the epitome of Fall fashion; a floppy hat, ripped jeans, plaid shirt, and crossbody bag. My boots are from Fashion Nova and a similar version can be found here.

So there it is kittens, three different looks with one simple plaid shirt. The one thing I truly love about fashion, is that you take something as seemingly one dimensional as a plaid shirt and turn into three separate looks that can work for any fabulous fashionista.

Always remember to be Fierce, Fabulous, and Fearless! *Muah*

Feel free to let us  know what you think in the comments section.

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Juliette and Jennifer
Juliette and Jennifer

Hey Y’all and Welcome to Southern Love! We’re Juliette and Jennifer a mother/daughter duo that lives in South Carolina. We created Southern Love to give people a real look into the lives of modern day southerners. You’ll be a able to find entertaining stories, amazing recipes, and southern decor.

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  1. September 23, 2019 / 3:40 pm

    Gorgeous!! I’m obsessed with all the looks, but the jeans are giving me life. Great post!

    • September 23, 2019 / 5:49 pm

      Thank you so much! I absolutely love Fall fashion, and I’m truly obsessed with plaid. I love these jeans, I put a link in the blog for a similar pair! Thank you for stopping by and for the wonderful comments!

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