From school uniforms to business attire to scarves to bathing suits to shoes to casual weekend looks, there is nothing plaid can’t do. At least, I’m convinced of that. A classic print with an air of preppy properness, plaid has been one of my favorite patterns to play with in my wardrobe.

Firstly, plaid is timeless, so I know pretty much any plaid-laden piece I add to my wardrobe can stick around for a while without becoming an embarrassing reminder of bygone trends. Secondly, it’s versatile as hell, so you can pair it endlessly with a rotating cast of stylish statement pieces and everyday basics for a look with polish and class. Thirdly, it makes me feel like a rich prep school kid with my whole life ahead of me, so, you know, that’s fun I guess!

In all seriousness, I do think that if you’re going to have any prints in your wardrobe, plaid should be one of them because you just can’t go wrong with it and it’s easy to style in a thousand ways, so each piece can feel brand new every time you wear it.

I’ve styled a few of my favorite plaid pieces into fun looks you could wear practically anywhere, for any occasion. Check them out below:

Plaid on Plaid Action

Whoever made up the rule that you can’t mix prints and still look good is a dirty liar. Introducing plaid on plaid AKA a power move. A blazer layered over a dress with a more subtle check pattern creates an interesting contrast, while the addition of the pleated skirt and sneakers adds a playful touch.

Blazer: Thrifted. Dress: Thrifted. Skirt: American Apparel (similar linked). Sneakers: Adidas.

Properly Plaid

Like I said, I love the proper, preppy vibe of plaid, which is why I chose to pair it with a classic, high neck, puff shoulder top that is a vintage thrifted find I absolutely adore. I styled the plaid dress as more of a tunic because it’s scandalously short, but I think it looked lovely over corduroy pants for contrasting texture in a complementary hue.

White Blouse: Thrifted. Plaid Dress: Forever21. Corduroy Pants: Urban Outfitters.
Boots: H&M.

A Plaid & Peplum Party

I absolutely adore finding new ways to layer clothing I’ve had for a long time. It helps to keep your wardrobe fresh and forces you to be more creative with your dressing. I think adding a darling plaid peplum top over a black sheath dress creates a glamorous, yet studious impression. The silver shoes over ruffled socks only serve to add to the overall whimsical vibe. I dare you to wear something like this to your next job interview. It’s unique and charming, what more could you ask for?

Plaid Top: Zara. Black Dress: Banana Republic. Shoes: Urban Outfitters.

Pleated Plaid Prep

Perhaps the most classic use of plaid is on a pleated skirt. Channeling the iconic energy of Scottish kilts and prep school uniforms, the pleated plaid skirt imbues any look with a sense of vintage class and the detached cool of a brooding English major that lays on the university lawn reading poetry. I paired mine with a bright fair isle sweater for a chic winter look and finished it all off with silver boots for a touch of shimmer because why not? The fern is optional but recommended.

Sweater: Thrifted. Plaid Skirt: Thrifted. Boots: Asos.

I really need to get back into posting style posts more regularly, but for now, I hope these pro-plaid ensembles give you some inspiration for your own winter wardrobes.