How to Put Together a Cute Plaid Skirt Outfit

Fall is the Perfect Time for Plaid

Once the first day of fall is in the books, not only does the urge for cozy knits and warm sweaters hit but also the desire to wear cool-weather prints like plaid. Plaids are so versatile, and come in a variety of patterns and colors and, because they are typically a fall print, you’ll usually find them in warmer materials as well, like wool.

This time of year you can find a variety of clothing in plaid, from pants and skirts, to shirts and jackets. You can try out a glen plaid, which consists of small and large checks in muted neutrals (black, gray, brown) that often have thin stripes of color (red, blue, green) running through the material. This pattern looks great in pants, skirts, and blazers.

Then there is the more traditional Scottish tartan plaids—multi-colored plaid designs with red, blue, green and black being the predominant colors. (Purple, yellow, orange, and browns/beiges can also be found.) This plaid is best left to skirts only, unless you happen to be visiting a Scottish castle in the Argyll highlands.

You might also try a window pane plaid, where the intersecting lines are farther apart. Good in a skirt or jacket. And then there is houndstooth—a plaid that tends to be very busy to the eye, so needs to be kept to a smaller area like a skirt.

The fall outfits you can create with plaid are endless. Take a look at the different types of plaid when you’re shopping and see which one you like the best not only to create your perfect plaid skirt outfit but look for plaid in other items as well.

So given the choices, you are most likely to find a cute plaid skirt in the stores right now, rather than pants. But don’t despair, plaid skirts are a great classic staple and will never go out of fashion. Invest in several good quality plaid skirts and you’ll be set for fall (and winter!) for years to come.

But, what to wear with a plaid skirt? Oh, let me count the ways!

How to Style a Cute Plaid Skirt Outfit

You can dress up a cute plaid skirt with a silk blouse and pumps, pair them with some knee-high boots and a chunky sweater to walk among the autumn leaves, or grab some flats and a denim button-down to go to work or on a weekend getaway.

The joy of plaid is that it can go grunge, punk, classic, classy, or anywhere in between. And because of the color scheme, each plaid skirt can pair with multiple colors—all solids, which will make your styling that much easier.

Let’s start with the skirt itself. To get the most wear out of it, keep it right around knee length. You can go a bit shorter or a bit longer, but too short or too long and it won’t be a classic you can wear every year. You can stick with a pencil or A-line skirt, or go traditional with a pleated plaid skirt. Again, any of these three styles will wear well for a decade or more (giving you more money in the future to spend on other things!).

Now let’s get to some plaid skirt outfit pairings…

Glen Plaid + Silk = this is the perfect business attire. A pencil skirt, long-sleeve silk blouse, and pumps and you’ve not only got an easy plaid skirt outfit, it can take you from the office to dinner and a show.

Tartan Plaid + Sweater Set = this is an iconic 1950s outfit that is classic and comfy. Look to J. Crew, Banana Republic, or Gap for a shell and cardigan set, preferably in a soft cashmere or wool blend. You can’t go wrong with this combo. Kitten heels would be perfect, but so would any pump or slingback or even a pointed-toe flat.

Window Pane Plaid + Denim = a more casual look, like I’m wearing. I paired a dark wash denim button-down shirt with a grayscaled plaid and some neutral flats. Good for a weekend brunch, a day of shopping or a casual work day.

Houndstooth + Chunky Sweater = will keep you warm all day long. This small checkered pattern can accommodate a chunky sweater, even if a cable knit or turtleneck. Just make sure that at least 4 inches of skirt hem are showing…you don’t want to hide that plaid! Finish it off with some knee-high boots to complete this plaid skirt outfit.

Plaid (any) + T-shirt + Moto Jacket = taking the plaid to the rugged side here. A simple cotton tee and leather motorcycle jacket is an urban standard. Add some Doc Martens and you’re good to go.

Plaid (any) + Turtleneck + Knee Socks + Loafers = a throwback to the ’60s runways (be careful not to look too Catholic schoolgirl). Not everyone call pull this off, but it’s a great look, so dare to be a rebel and look a little out of the ordinary!

Which plaid skirt outfit would you wear? Dressy, casual, or a throwback to the ’60s?

Not sure about plaids? Not ready to invest in a cute plaid skirt or pants? I want to encourage you to at least give plaid a try. Take a test drive with a scarf, perfect for those chilly fall mornings, and it won’t cost a lot. I think you’ll like it and be adding more plaid to your wardrobe in the future!

Stay Stylish!

Shop the Look

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Outfit Details

Flats from Tieks // Plaid Skirt from Free People (old) // Handbag from ZAC Posen // Chambray shirt from Banana Republic

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