Are you looking for plaid dress outfit ideas? The following ten outfit inspirations, each comes with three suggested alternatives, will surely help you plan out the best plaid dress outfit to join your wardrobe this fall and winter.
Plaid pattern always comes back as a favorite during cold seasons. Thankfully, plaid is size-friendly. That means, whether you lean more on the slim or the plus size side of the weight spectrum, there is always a plaid print that is perfect for you.
The only time you might want to be careful in choosing the plaid pattern is when you are short. Too big patterns will overwhelm your small frame, so look for medium sized plaid that suits you well.
When it comes to curating plaid dress outfit ideas, there are three things that you want to consider – the color, the size of the plaid print, and the style of the dress. Most dresses are straight forward, you´ll know right away how to wear and accessorize them, while some plaid dresses may need more planning on how to mix and match.
So let´s dive in.
1. Plaid dress outfit ideas: Black and white plaid dress outfit
The black and white plaid dress outfit is so easy to wear. Since it´s a monochrome, you´ll never go wrong with it. You may choose to keep the entire outfit a monochrome, or you can accent the look with bright colors. This is your call.
For this look however, I opted to keep the entire outfit a monochrome. I want the fierceness and the classiness of this look, which is often times difficult to achieve with plaid pattern. Since the dress has a shift silhouette and a gorgeous ruffled skirt, I teamed it up with some skinny thigh high boots.
A good parka that is cinched at the waist will keep you warm, while a black leather satchel shoulder bag is perfect to accessorize the look, while also being practical.
Similar Dresses
The shift ruffled plaid dress is also available in smaller plaid print, which may suit better on you if you´re amall and petite. You may also opt for a plaid shirt dress with rolled up sleeves instead, or a loose t-shirt dress with a swing silhoutte. All these dresses are available in different colors and sizes, including plus size.
2. Plaid Flannel Dress with Skinny Jeans
This plaid flannel dress is made for layering. It´s actually afour-season piece. In cold seasons, you can layer it with skinny jeans or warm tights. Add a black leather jacket and ankle boots for fall, or layer with a long wool coat in winter.
In summer and spring, you can drop the jeans or tights and wear the dress as is. Team it up with sneakers or ankle boots.
Similar Dresses
Although they are all plaid shirt dresses, they obviously have variations. You can go belted or not, and you can choose whether it´s a straight hem dress or with a high side/low front style.
3. Plaid dress outfit ideas: Vintage Plaid dress
If you love vintage dresses, plaid dresses should really be in your collection. There are many beautiful and gorgeous plaid dresses that are totally vintage in style or just vintage inspired.
The best thing about the vintage-inspired dresses is you can easily interpret it any way you want. For example, you style a vintage-inspired dress with current accessorize and make it look up-to-date. However, if embracing the style of the past is something you´d like to do this season, by all means try the swing plaid dresses.
So for the look above, I wanted to keep it feminine and more vintage. I added a pair of sling-back kitten heels. But I also wanted to keep it current by adding a bright orange structured handbag.
Similar Dresses
For a nice vintage plaid dress, go froa swing dress in a color that you love. You can wear them high heels, ankle boots (flat or with heels), and tall boots.
4. Plaid Bodycon Midi Dress
The plaid bodycon pencil skirt dress is so elegant that you can actually wear it to work. Long sleeves and figure hugging, this dress will carry you through the day without you shivering. Since it´s either a knee-length or a midi, it looks best when worn with high heel pumps or sandals. aoiv wearing it with boxy or loose boots. And definitely stick with stilettos.
Similar Dresses
Without prejudice, I would say that the plaid bodycon midi dress will look its best on a well-toned figure. But choosing the right plaid pattern can also help you create the illusion of a slimmer figure. Finer pattern with exphasized slim vertical lines will make you look slimmer than you actually are.
5. Plaid Dress with Long Sleeve Under
This may be one of the most popular when it comes to plaid dress outfit ideas. It´s probably because the dress is versatile. Whether it´s with spaghetti straps or with cami style, a plaid sleeveless dress can be layered with anything. You can layer it with long sleeve turtleneck tops in winter, or with puff-sleeve blouses in summer as seen on how to wear a slip dress.
To keep things warm, add a long wool coat and a pair of black thigh high boots.
Similar Dresses
There are many plaid dresses that can be worn with long sleeve under. Choose the color that suits you best, as well as the size of plaid print.
6. Plaid dress outfit ideas: Plaid A-line Dress for Work
This plaid A-line dress is perfect for work. With its classy style of plaid print, you can wear this dress to conquer the board room. Layer it with black tights and ankle boots in winter, or with opaque stockings and pointed-toe black pumps in summer. Although can wear the dress as is, you can always layer it with a black suit jacket.
Similar Dresses
Plaid dress outfits for work aren´t limited to A-line dresses, you can also opt for a sheath pencil dress, a retro-inspired bodycon midi dress, or a shift tunic dress.
7. Plaid dress outfit ideas: The Belted Plaid Dress
You can always update a dress with a belt. To give your plaid dress an edge, however, try cinching it at the waist with a wide belt. I really love how this square neck plaid dress transformed after a brown wide belt was added. It´s super chic.
Brown is a good color choice for the belt since the plaid print has brown in it. And of course, in order to make the look really polished, I added a pair of pointed-toe ankle boots in brown. But for the bag, I opted for a black leather bag in order to not give off a trying-hard or over-the-top brown look.
Alternative Dresses
You can choose any type of vintage plaid dress to wear with belt. It can be a cozy plaid sweater dress with balloon sleeves, or you can even choose an alread belted plaid dress. Whicever dress you´ll choice, make sure to enjoy your belted plaid dress outfit.
8. Plaid dress outfit ideas: Comfy and casual plaid dresses
There are also many everyday plaid dresses that are cozy and comfy. They are often loose, and sometimes with ruffles. You can go for either a long cozy plaid dress to wear with ankle boots, or a short cozy plaid dress to wear with sneakers.
9. Perfect Plaid Dress for Plus Size Women

As I´ve said earlier, the plaid print is size friendly. There are many plaid dresses that are made for plus size women. Take a look at this plaid midi dress with slim lines. although it´s plaid, the look is actually slimming. Wear this dress with strappy heels in summer, but in fall and winter, opt for slim leather ankle boots with stiletto heels and pointed-toe.
10. Plaid dress outfit ideas: Red Plaid Swing Dress for all Sizes
This red swing dress is perfect to wear this coming holidays. You can style it with Mary Janes to keep the entire look truly vintage, or you can complete it with a pair of more modern-looking high heels. This dress is available in slimmer sized to plus size.
So these are the ten plaid dress outfit ideas for fall and winter that I recommend to you. Remember to have fun with your plaid!