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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.

As winter unfolds around us and we marvel at how on earth another year could have passed us by so quickly, the Pre-Fall 2020 season is just getting started. While I have preferred to write individual articles chronicling my favorite collections each season, I opted to do one mega post of sorts this time around because I always plan on posting so many articles and never actually get around to writing them until they’re no longer relevant. I’m evolving, folks! So instead of feasting on one collection, we all get to snack on a tasting plate of the best collections this season has to offer.

Even though pre season shows are usually smaller and more commercial than their main season counterparts, I found a lot of looks to love in the collections I’ve browsed so far. The mood is predominantly romantic- flouncing sleeves, oversized silhouettes, layers of ruffles and daintily-feminine details abound. It’s no mystery why I loved so much of what I saw. It also seems like ’80s fashion is finally (regretfully) regaining its footing, with drop waist skirts and puffed sleeves making their presence known. But all in all, it was a surprisingly good season that made me wish I had any amount of money to actually buy all of the beautiful things I write about.

Check out my favorite collections (so far) below.

The Marc Jacobs

Marc Jacobs for the masses, The Marc Jacobs is a luxury brand built for the age of Instagram, with a decidedly young, whimsical vibe that photographs so easily and so well. Created in collaboration with at least six other artists and designers, the collection is rife with darling details and supremely-wearable pieces to mix and match for a variety of occasions. My favorite pieces are the Victorian-inspired dresses (of course!).

Photos courtesy of The Marc Jacobs via Vogue.com.

Jil Sander

A serene combination of Jil Sander’s signature minimalism and playfulness defined their Pre-Fall collection. Clean lines and classic pieces were refreshed with surprising twists, like a long dress in a soft mohair material, or a crisp blouse with detailed cutouts. This push and pull created pieces that are not only extremely wearable, but also delightful.

Photos courtesy of Jil Sander via Vogue.com.

Fendi

Always impeccably-styled and artfully-designed, Fendi almost never fails to impress me (even if they still use real fur in their dreamy creations). This season, they evoked the character of an aristocratic Lolita, with classic, indulgent silhouettes getting a slightly subversive makeover (see: sheer ruffled skirts and too-short babydoll dresses). I found myself drawn to the mix of rich textures- corduroy-esque suede, quilted skirts, chunky knit bralettes, sheer, flowing layers- each look is more dreamy than the last.

Photos courtesy of Fendi via Vogue.com.

Dsquared2

Mimicking the preppiness of sportswear (meaning things worn by people who actually play sports), the stylishly-layered looks in this collection exude a perplexing and pleasurable rhapsody of high-class snobbery and down-to-earth coolness. I love the chunky sweaters, the suits paired with equestrian blankets, the oversized scarves- it all makes me wish I went to college in a blustery Ivy League in the bougie northeast. I am a huge prep fan at heart, so this collection played into all of my darkest wardrobe fantasies, making me want to layer at least one sweater over everything.

Photos courtesy of Dsquared2 via Vogue.com.

Adam Lippes

Lippes knows what his customers want: Practical pieces with a whimsical touch. Featuring a plethora of feminine frills like sheer, snap-on collars, tie neck blouses, and ruffled skirts, this collection certainly delivers. As an avid user of the white blouse layered under things styling trick, this collection spoke directly to my sensibilities while proving to everyone that I might actually be onto something with my unwavering desire to layer everything all the time (and my lack of control when it comes to buying white blouses).

Photos courtesy of Adam Lippes via Vogue.com.

Tory Burch

Inspired by the spirit and style of aviator Amelia Earhart, Tory Burch traded in uptown polish for menswear-inspired sportiness with an adventurous vibe. Many pieces featured details inspired by bandanas and scarves, an essential element to an aviator’s ensemble. I found myself drawn to the crisp, yet relaxed linen, as well as the vintage-inspired silhouettes of the dresses and jackets.

Photos courtesy of Tory Burch via Vogue.com.

SEA

Known for creating pretty pieces with a feminine flourish, this season saw Sea expand on that femininity to include trippy, imperfect prints and hand-quilted materials that give their clothes a more rustic vibe. Because I’m a fan of flowy, ruffled dresses that you might have seen someone wear on a farm 200 years ago, their selection of relaxed frocks that fit this bill definitely caught my eye. But it was the delightful quilting that made me linger- just another reminder to me that I need to learn how to sew, so I can someday hope to make something half as beautiful as these pieces.

Photos courtesy of SEA via Vogue.com.

How do you feel about the Pre-Fall 2020 fashion collections? Let me know which collections are your favorite, so I don’t miss out on anything good!