10 Different Ways to Style a Shirt Dress Outfit For Fall & Winter

Wondering how to style a shirt dress outfit for fall and winter? I’m going to show you 10 long shirt dress options to give you plenty of styling inspiration.

A shirt dress is such a versatile piece because you can either wear it as a dress or you can unbutton it and wear it as an outerwear piece. Here, you will find out how to wear one in lots of different ways!

How to style a shirt dress

1. Perfect layers

Start off with a black turtleneck, black trousers, and a pair of monk shoes. Break up the all-black ensemble with a red plaid shirt dress and a brown cardigan.

Layering two outerwear pieces of similar but different lengths looks very voguish.

How to wear a shirt dress with a belted scarf

2. Standout scarf

A red check shirt dress looks great over a turtleneck sweater. When you need some extra warmth, just throw on a coat. Add a large scarf to keep you warm in the cold.

Tying the belt of the coat on top of the scarf is a fun detail that really makes the scarf pop.

Cute shirt dress outfit

3. Sweater style

A plaid shirt dress with a sweater dress, a leopard-print scarf...

Hipster shirt dress outfit with a hat

...or a poncho scarf, plus over-the-knee boots, lend warmth in the cold.

The flannel material of the shirt contrasts nicely against the cotton sweater dress. For a fun accessory, throw on a wide brim hat in the same shade as your plaid.

How to wear a shirt dress with shorts

4. Print & play

Wondering what to wear in the winter? Why not have fun and play with prints? Style your check shirt dress with tailored shorts, combat boots, and a leopard-print scarf.

It's an unexpected combination, but sometimes it's fun to think out of the box.

Can you mix plaid prints together?

5. Plaid on plaid

Choose a base color and add different shades in varying prints to make it all fit together. Then rock two different plaids!

Wearing a shirt dress with a Breton top

6. Stripy chic

A thick black and white striped sweater and black trousers play well with this red check shirt dress. Complete this smart-casual outfit with a pair of white sneakers, a black coat, and you are good to go.

Wearing a shirt dress under a sweater

7. Under a sweater

Striped sweaters definitely don’t have to read preppy. Add combat boots and fishnet tights. Layer up a plaid shirt dress with a striped sweater and a parka for an edgy, punk-rock-inspired outfit.

Undo some of the buttons at the bottom to create a slit in the skirt and show a bit of leg.

How to layer a shirt dress outfit for winter

8. Blazer up

Ok, this one is definitely preppy. A cream turtleneck and a blazer over the shirt dress create a more formal outfit.

Add a pair of crew socks for a clean and cute '60s look, like Beth Harmon from The Queen’s Gambit.

Smart casual shirt dress outfit ideas

9. Pop of color

Combining a blazer with a shirt dress can be stylish for a smart casual outfit. Colorful socks, black heels, and leggings make the outfit feel more stylish and put together.

I opted for mustard-brown socks that are light enough to add some color but still work well with the dark tones of the outfit.

Shirt dress outfits for fall and winter

10. Leggings

If you want to wear a dress with leggings, think shirt dress. Shirt dresses look most like long shirts and will work the best.

Shirt dress outfits for fall and winter

A shirt dress is such a versatile piece and great to have in one’s wardrobe. There are so many different options for how you want to style it that you can really just unleash your creativity.

Let me know your favorite outfit out of the ones I styled in the comments below!

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