How To Wear A Plaid Shirt For Every Occasion

Plaid and fall go hand in hand. I always love plaid so much because, in general, I only wear it in the fall and winter. I wear a lot of festive holiday plaid too so I feel that my main plaid wearing days fall between October and December. For this reason, plaid always feels special to me! I find myself wiggling my toes every year when I reach for my plaid pieces. It only means that the most festive time of year is here!

Every type of plaid is just perfect to wear in the fall and winter… tartan, glen plaid, black watch, tattersall, houndstooth, gingham, windowpane check, madras… I’ll take it all! Plaid comes in so many beautiful forms this time of year like coats and dresses as well as so many cozy layers like flannels and scarves so it’s really easy to add plaid into your fall wardrobe. However, today, I’m going to be focusing in on my most go-to plaid piece, the plaid shirt!

Shirt (c/o, also available here, similar here) / Jeans / Loafers

How To Wear A Plaid Shirt For Every Occasion

On a Lunch Date

Heading out the door for a lunch date with girlfriends or a colleague? Pop on a plaid top for a comfortable but effortless fall look. If you are meeting friends, then pair your plaid with skinny jeans. Add loafers or ankle boots for a low key look. On the other hand, if you’re meeting a work colleague, then wear a plaid top with a midi skirt or pencil skirt for a more polished look.

On a Fall Outing like Apple Picking or to a Pumpkin Patch

When I’m out enjoying a classic fall outing like apple picking or visiting a pumpkin patch, I keep it really casual. You might find me wearing a flannel shirt or wearing a plaid shirt worn open with a white tee or simple tee underneath and a pair of blue jeans (as seen in this Jackson Hole look). It’s all about comfort while still looking cute and quintessentially fall!

To a Tailgate or Football Game

For an outdoor tailgate or a football game in the fall, you can pretty much expect cooler temperatures. This is obviously especially true if you’re heading to a night game! For this reason, I recommend wearing a plaid shirt around your waist to have as an extra layer when night falls. It might not sound like something I would do, but when I head back to my college campus for a fall football game, I like to really get in the spirit and be “on theme” if you will. So a plaid shirt tied around the waist is a direction I often take! I’ll even bring a denim jacket or a puffer vest or coat (as seen with this corduroy look, this stripes + plaid look, and this riding boots look) for another layer for night games (temps drop in Boulder, where I went to school).

Out for Drinks or to a Cocktail Party

I’ve shared a few examples of when I wear plaid in a very casual way but what about when I want to dress plaid up a bit? It’s completely possible! I would definitely wear plaid out for drinks or to a cocktail party. It really is one of my fall/winter/holiday wardrobe staples. To give my plaid top a little edge and make it dressed up a bit for date nights with Edwin out to drinks, I might add on a leather jacket or wear my plaid top with black jeans instead of blue jeans. I also might add on a dressy accessory like a fur stole or a statement earring (as seen on this holiday bike ride). Just like that, your plaid is dressed up!

To Dinner

When heading out to dinner, I pair a plaid top with a skirt for a nicer nighttime look. Plaid can be busy so I think a plaid top looks fantastic with solid colors on the bottom. For skirts, I love the idea of tucking a plaid top into a short, midi, or maxi skirt (as seen in this Charleston look) just as much as I love the idea of tying up a plaid button-down around the waistline with a skirt (as seen on my sister). Add a pair of over the knee boots to a mini skirt outfit to make it more fall appropriate. Or, add a pair of booties to a maxi skirt outfit to complete the look.

To a Holiday Party

I don’t know about you, but I find plaid to be incredibly festive for the holidays! I find that I prefer a plaid top over a plaid button-down for holiday occasions as they are a bit dressier. It’s so easy to dress a plaid top up with a pop of fur, statement earrings, a bold lip, and a dressy coat. Plus, you’ll be the most comfortable person at the party! Get some inspiration for this look here!

I hope this post gave you some inspiration for how to style a plaid top for every occasion! Tell me, do you love plaid as much as I do? What’s your preferred way to wear plaid in the fall? xx