Ways to Wear Plaid Effortlessly this Fall

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A few weeks ago, we wrote a post about this Autumn’s animal print trend effortlessly wearable. Keeping in line with recent posts about fashion trends for this Fall, we are discussing ways to wear plaid. This is one staple that we think never goes out of style up here in Canada, but it is also one that is more prominent some years than others. We all have the classic warm and cozy plaid flannel shirt in our closet from Fall and Winter’s past, but this year retail stores are carrying more than just your usual plaid styles.

Ways to Wear Plaid: close-up of sweater dress and plaid shirt

In fact, most stores have an abundance of plaid ready for the wearing in this up and coming season. From comfortable pajamas and leggings to more dressed up pant sets, blazers, dresses, long-line jackets, skirts, and even accessories, you will find there are plaid options to fit any style preference. When we think of ways to wear plaid, three main categories come to mind: casual, comfortable or warm, professional office work-wear, and the stereotypical school-girl trend of plaid short skirts and dresses.

Ways to Wear Plaid: Two Piece Sets and Casual Skirts/Dresses

We don’t like stereotypes, but that is the best way we could think to describe the classic uniform style that people have come to associate with plaid over the years. We love that retail stores are carrying variations of this same look in abundance this year. This particular style tends to favour pleated skirts, mini-skirts, and short pinafore dresses. Heading into Autumn this year, we are also seeing numerous two-piece outfits available to mix, match and play with as well. As you can well imagine, Fashion Nova carries a great and fairly inexpensive plaid pant and crop top set. I like this look for early Fall days when you know the weather will vary throughout the day and need to rock layers to stay comfortable. This one, in particular, has a white base so it is actually a good light option to end the summer with as well.

Casual Dresses

Besides trendy two-piece sets, plaid dresses have been updated for the season as well. Forever 21 online has options starring large buttons or O-ring zippers. In the past, we might have let the plaid print steal the show, but these pieces are a seamless way to carry the beautiful focus on button details we saw in the Spring and Summer into another season.

In particular, we like this suspender dress from Forever 21 because of the linen fabric from which it is made, as well as the large tortoise-shell buttons. Linen is the fabric you want to wear for any of the hot days remaining this summer. This plaid pinafore option from Forever 21 also features large and in charge buttons, but is made of polyester, rayon, and spandex. Retail price for both is only $33.90CAD and they are both great for mixing, matching, and layering with other pieces in your wardrobe heading into the new season.

Casual Skirts

Ways to Wear Plaid: Checked short skirt
This plaid mini makes an appearance from my wardrobe every fall. Usually, it gets paired with Black tights, black booties, and a basic tee or chunky sweater depending on the temperatures outside. In particular, we love its girly fit and the beautiful grey/green shades in the pattern. It is one of those classic pieces that you can always wear stylishly.

As you might have guessed, casual plaid skirts are up for discussion next. There are, of course, your usual mini and short pleated options in your typical patterns available. We have noticed a wonderful increase in shade and tone selection. This year we have seen various throwbacks to your enviable classic Cher from Clueless styles. The popularity of these bright plaids makes our younger selves giddy and nostalgic.

This pink mini-skirt from Urban Outfitters is our favourite colourful one. It retails for $59CAD. This skirt would look awesome styled up with a pair of chunky boots heading into the new season. It would be great with taller boots and a chunky sweater for those colder days.  Forever 21 also carries bright skirts and unusual hemlines if you are looking for a unique casual plaid skirt. This bright blue one retails for $30.90CAD and is another one that is perfect to layer. This terrific Tie-Front Mini combines two popular trends from this year: plaid and the wrap-style for the low price of $33.90CAD.

Ways to Wear Plaid: Professional Office-Wear


We love these plaid midi-skirts for Fall. They are sophisticated while allowing you to be playful in your office outfits. With this one inexpensive skirt from Forever 21, you can create a number of different looks when you incorporate pieces you already own from your own closet. Who doesn’t love that? If we purchase this one, it will likely be paired with heels or mules and a basic tee or tank.

We would also be sure to carry a plain jacket or chunky sweater to keep warm. The button details are one of the best parts of this piece, again bringing summer style into fall. The skirt is 100% rayon, which is always nice to find at Forever 21. It retails for $26.90CAD and is another one of those lightweight pieces that will work to transition seamlessly from summer into fall.

Ways to Wear Plaid: Blazers

There are obviously checked blazers and jackets everywhere in Fall style this year. It is easy to throw one on with more basic outfits to automatically make them more trendy. When you add a blazer or long-line plaid jacket to an outfit, you feel more sophisticated. You are automatically able to take on the day. They always add an air of thoughtfulness to your outfit. This is true even if the most thought you put into it was regarding which blazer to purchase and rock on repeat. Depending on the style you choose, it is a simple way to incorporate the boyfriend style into your everyday feminine look. An option like this one from Bershka (available on ASOS for $51.55CAD) is versatile for the exact purpose described above.

Ways to Wear Plaid: Trousers

One of the other obvious articles of clothing needed for a professional wardrobe is trousers. I am sure you are aware there are numerous checked options available here as well. The entire inspiration behind this article comes from a pair of trousers offered at RW&Co. We came across them one day in the mall and fell in love. These ones are ideal for the office. You can stylishly dress them down for the weekend with a nice tee, tank, or sweater.

They are almost a paper-bag waist style, with the high-rise and tie-detail.  They also feature a cuffed-hem at the bottom. These trousers retail for $89.90CAD, but are currently on sale for 30% off. In our experience with RW&Co apparel, it is often worth it to spend the extra money if it is a piece you can get away with wearing for a long time. The quality, in our experience, is quite admirable.

Ways to Wear Plaid: Checked trenchcoat
Another of my staple plaid pieces will be this trench-coat. I purchased the one above a few years ago and am still in love. The classic trench-coat style is always classy and the simple grey plaid pattern adds an extra something to the piece. This lightweight jacket comes out to play every Autumn until the cold weather really hits. This year I am aiming to find a heavier duty long-line plaid jacket to become another go-to. I am sure, if you follow me on Instagram, you will see one there before too long.


Ways to Wear Plaid: Casual Flannel Shirts, Leggings, and Pajamas

We think pieces in this section are most common. Casual is one of the most prominent styles in which you can find plaid. If you enter nearly any store here around this time of year, you will see some sort of plaid button-up. They are usually standard red, blue or green colour. More feminine pieces focusing on purple and pink shades are available.

Ways to Wear Plaid: Blue and red checked shirtWays to Wear Plaid: Green and white checked shirt

The shirts often have an oversized fit so you can wear them in many different ways for different occasions. They are warm enough to use in transitional weather instead of a sweater and comfortable enough to lounge around in at home.

You can dress them up a bit for Casual Friday in the office as well. Many people rock these long shirts with leggings or skinny jeans and tall boots during the colder weather as well. These shirts are one of the easiest ways to wear plaid.  We do not believe casually designed plaid pieces will disappear from real Canadian life any time in the near future. It is always nice to see everyone else enjoying plaid as much as we do!

Ways to Wear Plaid Sweater dress and plaid shirt styled

Ways to Wear Plaid: In Summary

There are so many new articles of clothing available featuring plaid patterns this year. This is a long post and we did not even manage to touch on accessories or layering plaid upon plaid. To summarize that trend, models on the runways were wearing different plaids layered on pieces over top of each other. It is an interesting look, but we are not sure if we could pull it off on the streets. Let us know if you will be wearing plaid this year. If you plan to, how will you rock it? What pieces are you picking up or what do you already own from Autumn’s past? If you like posts about style and trends, check our other style pages out here.

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