‘Tis the season… for plaid! It’s a staple from fall through winter, and there are so many different ways to wear your favorite plaid tops! So let’s break them all out and get the most out of them this season with these seven plaid shirt outfits perfect for the holidays and beyond!

Seven Plaid Shirt Outfits Perfect for the Holidays

Since I’m styling my tartan plaid shirt from Madewell, these plaid outfits are giving me all of the holiday vibes! But don’t feel like these outfits are strictly for the holidays! You can use these outfit formulas with all of your plaid shirts, regardless of the time of year!

My exact top is more of a boyfriend fit, but I’d recommend sticking with your true size, especially if you want to recreate some of the leggings outfits! If you’re looking for a more affordable option, I also found this very similar option at Old Navy! The Old Navy version has more of a classic fit, so I’d suggest sizing up one! But of course, like I mentioned, you can use whatever plaid shirt you already have in your closet!

And if you’re looking for ways to wear a solid flannel shirt, check out my seven white flannel shirt outfits! You can also use those ideas with your plaid tops!

Sweater Blazer and Plaid Shirt Outfit

We’re starting off with leggings, mainly because it’s all I want to wear this time of year. Once it gets cold outside, being cozy is my top priority! I started with my trusty Spanx faux leather leggings and plaid. To create a more tailored look, I topped the outfit with my sweater blazer! I mention this all the time, but a sweater blazer has become one of my favorite staples. It’s cozy, yet polished. (More sweater blazer outfits!) And even though I’m in leggings, with the blazer and a pointed toe mule, the outfit looks chic!

To dress this outfit down, I would swap the mules for a sneaker. You could make it even cozier with an oversized cardigan. You’ll see this combination later in the post!

Plaid Shirt Layered with a Striped Tee

Do you layer up your plaids? If not, you’re missing out on such a fun (and warm!) outfit combination! To make the mix of stripes and plaid work, I stuck with two options that have similar colors! The dark stripe of my tee picks up on the darker plaid stripes. The wider white stripe doesn’t compete with the scale of the plaid either! As another option, I also love layering with a striped turtleneck! If stripes and plaid are too much for you, just stick with a solid option! A plain white long sleeve tee (or turtleneck!) would be perfect here!

To keep with a classic but still on-trend vibe, I went with my straight leg jeans and a lug sole boot. Any bootie would work here, but I’m loving the lug sole of these chelsea boots. Lace-up combat boots would work here too!

Cardigan and Plaid Shirt Outfit

Since cropped and shorter cardigans are one of the most popular sweater styles this year, I had to include one with plaid! Most of the time, I reach for my longer cardigans when it comes to layering. But this cropped version works just as well! Be sure to tuck your plaid with shorter cardigans to keep the look polished. Tucking also helps keep the proportions in check, since cropped cardigans will be shorter than the length of an untucked button down.

For a little playful touch, I also added a leopard bootie! I love a little leopard mix with plaid! If print-mixing isn’t for you, a solid bootie is a great option too. Or keep it more casual with a white sneaker!

Knotted Plaid Top and Wide Leg Pants

These wide leg pants are a great option for a slightly more dressed up outfit! You could tuck the top in, but I love the look of a knot at the waist! It helps define the waist and is a fun feminine detail. Black pumps align with the dressier vibe I was going for, but a pointed toe flat would be equally as chic! You could also make this look more casual by swapping for a sneaker and throwing on a denim jacket!

Leggings, Plaid, and Long Cardigan Outfit

Here is the outfit I was referencing in my other leggings outfit description! It’s a slightly more laid-back and casual version of the sweater blazer look! It still has the same base of Spanx leggings and plaid! But you’ll see that with a more oversized long cardigan, it pulls much more casual and cozy than the blazer version! For days at home, when I want to get dressed but stay comfortable, this is one of my go-to outfits!

Plaid Top and Jogger Pants Outfit

And speaking of cozy, comfortable outfits, I had to include a jogger pants look! If you haven’t tried pairing joggers with a button down, just trust me and do it. It’s so stinkin’ comfortable but I still feel pulled-together enough. It’s the ultimate combination of comfort and fashion. This is 2020 in an outfit. 😂

My top recommendation when creating this outfit is to make sure your jogger pants are on the more tailored side. You won’t want to wear a super-oversized pair with a button down to prevent from looking sloppy. Adding a third piece, in this case a vest, helps complete the look too. I also recommend trying a denim jacket, cardigan, or sweater blazer!

Open Plaid Top and Bodysuit Outfit

Although similar to the layered striped tee look, this outfit uses an open plaid top layered over a bodysuit! The shirt-jacket look is big this year and so easy to accomplish with a bodysuit or fitted tee underneath!

To keep the outfit on-trend, I paired it with combat boots. But for a more casual everyday option, you could swap for sneakers! If you don’t have a bodysuit, try a plain tee or graphic tee underneath! Of course stripes and turtlenecks work too as in my striped tee outfit!

Which of these seven plaid shirt outfits would you wear?! Don’t forget to check out my seven white flannel shirt outfits for more inspiration!

See more items styled multiple ways in my style sessions series!