What to Wear With a Plaid Shirt: 5 Comfy & Trendy Fall Outfit Ideas

In this styling guide, I'm going to show you what to wear with a plaid shirt, by sharing five of my favorite plaid shirt outfit ideas for fall. Does anyone else love plaid shirts as much as I do? I’m not the sort of person who gravitates towards patterns, but when I do, it’s usually plaid.


I feel that plaid is always a staple in fall wardrobes, and I personally don’t think that it will ever go out of style. If it does, I’m going to keep buying it because that’s how much I love it!

The star of this tutorial is a neutral plaid-button-up that has a slight balloon sleeve. It’s beige with a black and white plaid print, but you could replicate these plaid shirt fall outfits with any plaid print shirt that you want.

Plaid shirt with a midi skirt and tights

1. Plaid shirt with a midi skirt

For this first outfit, I paired my plaid shirt with a pleated midi skirt. To add some pizzazz and a little bit of interest, I added a pair of sheer polka dot stockings.


To finish the look off, I’m wearing ankle boots and a snake print belt around my waist that you might notice is the same color palette as the plaid shirt.


This outfit looks very elegant, and if you’re stepping out, you could throw a long trench coat over the top.

Plaid shirt with an oversized blazer

2. Plaid shirt with an oversized blazer

This outfit is a little bit simpler. I paired some high-waisted straight-leg denim jeans in a darker wash with a tan blazer that is a little bit oversized that again matches the color of the plaid button-up.


On my feet, I have a pair of nude pumps with a golden heel that adds a little bit of bam. This outfit also looks very put together.

Plaid shirt over a turtleneck

3. Plaid shirt over a turtleneck

Can I just say how much I love this look? It’s very casual, loose-fitted, comfy, and maybe a little bit androgynous as well.


I’m wearing some black chino pants with a black turtleneck. I layered the plaid shirt over the top, and I left it unbuttoned at the top and did a loose tuck, so it has a baggy look to it.


A pair of ankle boots finishes the outfit off.

Plaid shirt with leather pants and boots

4. Grungy plaid shirt outfit

Now my inner rocker/grunge girl has come out! I left the shirt unbuttoned, so I’m kind of wearing it as a jacket and paired it with some high-waisted leather pants and over-the-knee leather boots.


I tucked in an oversized black tee, but this would look nice with a graphic tee as well. I’m loving this rocker vibe.

Plaid shirt with a miniskirt and high boots

5. Plaid shirt with a miniskirt and over-the-knee boots

I saved the best till last. If you want to be sexy and comfortable at the same time, then this is the outfit for you. I paired a black miniskirt with over-the-knee tan boots, and for some added coziness, I added on a chunky long-line black cardigan.


You could wear the button-up shirt loose and untucked, but you could also tie it at the waist if you want something a little more fitted. I love how you can effortlessly throw this outfit together, and it looks completely awesome.


What to wear with a plaid shirt

Those are my five plaid shirt outfit ideas for you. You can wear it tucked or untucked, tied or loose, buttoned or unbuttoned, and as a shirt or as a piece of outerwear.


Spice up your everyday outfits by playing around with these different options and see what looks you can create!

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