Happy Monday, Grit & Glammers! If you’ve been around here for a few autumns, you know I’m mad for plaid the minute the weather turns — and this year, a green and red tartan shirtdress has me thinking well past October. A plaid shirtdress for the holidays is one of those rare pieces that can carry you from a crisp fall afternoon to Thanksgiving dinner and right on into a Christmas party, with only a few changes along the way. (If you missed it, I shared five ways to wear a shirtdress in fall this summer — consider this the holiday sequel.)
What I’m wearing: Plaid Shirtdress (wearing a size 8, fits true to size) · Double Buckle Belt · TLock Handbag · Suede Slingbacks · Thin Gold Hoop Earrings · Bamboo Bracelets
Key Takeaways
- A plaid shirtdress for the holidays works from fall through December because the dress stays the same — you change the belt, the shoes, and the layer on top.
- For Thanksgiving, knee-high boots, a camel coat, and warm cognac and gold keep it relaxed and ready for a long day with family.
- For Christmas, black velvet, satin slingbacks, and one sparkling belt dress the same tartan up for evening.
How Do You Style a Plaid Shirtdress for Fall and the Holidays?
Keep the dress and change what goes around it. Swap the self-tie belt for leather, then let your shoes and top layer set the occasion—boots and a camel coat for daytime gatherings, heels and a velvet blazer for evening. Repeat the dress’s own colors in your accessories, and one tartan shirtdress can carry you through the entire season.
Why a Plaid Shirtdress Earns Its Place This Time of Year
The calendar fills up quickly between October and New Year’s, and I’d much rather spend those weeks with the people I love than standing in front of my closet. With three granddaughters in the family now, the holidays have more little hands in them than ever — and I want a dress I can sit on the floor in, sit down to dinner in, and still feel put together in when the photos come out.
A shirtdress has always been one of my Classic Style favorites for exactly that reason. It’s polished without being fussy, and the button front, collar, and full skirt flatter just about everyone. Choose it in a tartan with red and green running through it, and it already feels seasonal—no extra effort required.
I’ll admit that wearing the same dress to more than one celebration is part of the appeal for me. At this stage of life, I’m far more interested in clothes that work hard and earn their keep than in something new for every occasion. One good dress, styled three ways, feels like a much better use of a closet — and a budget.
How I Styled My Plaid Shirtdress for Fall
The Plaid Shirtdress came with a self-tie belt, but I set it aside for a cognac leather Double Buckle Belt. The two buckles give the waist more shape and pull in the warm brown that makes plaid look like fall. From there, everything stays in that same cognac family — the TLock Handbag and a pair of Suede Slingbacks — with Thin Gold Hoop Earrings and Bamboo Bracelets to finish.
Splurge & Save: TLock Handbag · Dupe Handbag
The fall outfit formula:
- A plaid shirtdress with a defined waist
- A leather belt in place of the self-tie
- A structured bag and shoes in one warm brown
- Simple gold jewelry
✨ Beth’s Style Tip: Trading the self-tie for a leather belt is the easiest upgrade you can make to any shirtdress. Fabric belts tend to look like part of the dress, while leather looks like a choice you made — and it gives you a place to bring in the color story you want for the day.
A Plaid Shirtdress for Thanksgiving
Thanksgiving is a long day — cooking, eating, visiting, and usually a few hours of chasing little ones — so I wanted this version to be warm, relaxed, and easy to move in. Knee-high boots are the anchor here. With a midi length, the hem meets the top of the boot, so there’s no gap of bare leg, and the block heel on these Suede Knee Boots is kind to your feet when you’re up and down all afternoon.
Over the top, a long Camel Coat is about as Timeless Style as it gets with tartan. If your coat is a little shorter than your dress, let a few inches of plaid peek out below the hem — I think it’s charming. A soft Printed Scarf adds warmth for the walk in, and a Woven Crossbody keeps your hands free for carrying a pie or scooping up a grandchild.
For the belt, I chose something different from the cognac belt I wore in my photos: the Suede Ring Belt, which pulls a tonal green from the plaid. A pair of Gold Hoops finishes the look.
The Thanksgiving outfit formula:
- Plaid shirtdress + suede knee-high boots
- A long camel coat and a soft scarf
- A hands-free crossbody in warm cognac
- A tonal belt and gold hoops
A Plaid Shirtdress for Christmas
For Christmas, the same dress moves into evening, and the warm browns step aside for black, red, and a little sparkle. A black Velvet Blazer takes the place of the camel coat — it’s fitted and ends at the hip, so worn open, the waist and full skirt still show. Velvet with tartan is one of my favorite holiday pairings, and it feels festive without feeling like a costume.
The Embellished Belt is the one statement piece, and its crystals are set on black, so it ties right in with the blazer. Better still, it has an elastic back, which you’ll appreciate after the second helping of dessert. Black Satin Slingbacks with little bows keep the shape of the slingbacks I wore in my fall look, just dressed up for a party. One practical note: satin spots water easily, so save these for the party itself rather than the walk across a wet parking lot.
A Red Satin Clutch pulls the red straight from the tartan. Because you carry it in your hand, away from the dress, it reads as an accent rather than a match — far less “Christmas parade” than red shoes would. Moissanite Pear Earrings and a lariat-style Crystal Necklace finish things off, and their teardrop shapes echo each other nicely.
✨ Beth’s Style Tip: A lariat needs an open neckline to really shine, so unbutton your shirtdress a button or two and let the drop settle into the V. It lengthens the neckline, keeps the pendant sitting well above the belt, and takes a daytime collar straight into Christmas-party territory.
The Christmas outfit formula:
- Plaid shirtdress + a fitted black velvet blazer
- One sparkling belt as the statement
- Black satin slingbacks
- A red clutch pulled from the plaid
- Silver jewelry with a little shine
And when January arrives, the dress doesn’t have to go back in the closet. I shared a few ideas on how to wear plaid after the holidays that still hold up today.
More Shirtdresses to Love This Season
If red and green tartan isn’t quite you — or you’d like a second shirtdress in the rotation — here are five more that would take the same Thanksgiving and Christmas styling beautifully. The Tartan Shirtdress in navy and green gives you plaid that feels a little less Christmas, while the Navy Pleated Shirtdress is the polished solid that works with every piece on both boards. The Knitted Shirtdress is the cozy choice for chilly days, and you know I can never resist a little leopard, so the Leopard Shirtdress made the cut. The Polka Dot Shirtdress has short sleeves, so it’s a lovely early-fall pick or one to layer under a cardigan as the weather cools.
Closing Thoughts
I’ve loved plaid for a long time — you can see it in my plaid shirtdress post from a few years back — but what I appreciate more these days is how much one good piece can do. A plaid shirtdress for the holidays isn’t about having a new outfit for every gathering. It’s about having something you love that’s ready when the invitations come, so you can spend less time getting dressed and more time with the people around the table.
Change the belt, change the shoes, add a coat or a blazer, and the season takes care of itself.
Style has no expiration date — and neither do you.
Frequently Asked Questions
Can you wear a plaid shirtdress for the holidays?
Absolutely. A tartan with red and green feels festive on its own, and the classic shirtdress shape makes it easy to dress up or down. Change the shoes, belt, and top layer to match the occasion.
What shoes go with a plaid shirtdress?
Knee-high boots work beautifully with a midi length for daytime and cooler weather, since the hem meets the boot. For evening, a black satin slingback or pump keeps the focus on the plaid.
How do you belt a shirtdress?
Swap the self-tie for a leather belt at your natural waist to give the dress more shape. Choose a belt in a color pulled from the print, or try a double-buckle belt for a little more interest.
What do you wear over a shirtdress in winter?
A long camel coat works well for daytime and travel, and a fitted blazer that ends at the hip is the dressier choice for parties. Wear either one open so the belted waist still shows.
What jewelry goes with a plaid dress?
Keep it simple, since the plaid is already busy. Gold hoops are easy for daytime, while a lariat necklace and drop earrings add a little sparkle for evening without competing with the pattern.
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Featured Outfit
- Plaid Shirtdress
- Suede Slingbacks
- Double Buckle Belt
- TLock Handbag
- Dupe Handbag
- Thin Gold Hoop Earrings
- Bamboo Bracelets
For Thanksgiving (numbered to match the board)
- Plaid Shirtdress
- Camel Coat
- Printed Scarf
- Gold Hoops
- Suede Knee Boots
- Woven Crossbody
- Suede Ring Belt
For Christmas (numbered to match the board)
- Plaid Shirtdress
- Velvet Blazer
- Crystal Necklace
- Moissanite Pear Earrings
- Embellished Belt
- Satin Slingbacks
- Red Satin Clutch
More Shirtdresses (numbered to match the board)
- Polka Dot Shirtdress
- Tartan Shirtdress
- Leopard Shirtdress
- Knitted Shirtdress
- Navy Pleated Shirtdress
Before You Go
Do you have one piece you reach for every holiday season? Tell me about it in the comments — I’d love to know what’s waiting in your closet for Thanksgiving and Christmas this year.
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