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How To Be Preppy AF

When I was in elementary school, kids referred to as “preps” were the kids who wanted everyone to like them; they were overly-nice to win the crowd over, and they were made fun of for being so. I had this idea in my head of what it meant to be “preppy,” until later in high school. My best friend was already preppy when I met her, and definitely influenced my style choices over the last few years. Being preppy, and dressing like so, does not equate to people who are looking for the approval of others, but people who define their style in a highly particular, calculated way. That specific style can be summarized as bright, layered, and polished. If you’re looking to indulge in the preppy lifestyle, you’ve come to the right place. Here are the best ways to achieve your status as “Preppy AF.”


Your Planner

It’s not just a planner- it’s colour coordinated, it’s hard cover with a coiled spine, and it’s likely Kate Spade or Lilly Pulitzer. Oh, and it’s overpriced. 


Layer everything. Button downs, knit sweaters, vests, flannels. A go-to outfit, in the fall especially, is a button-down/plaid flannel under a V-neck knit sweater, polished off with a light vest. Too many layers? That’s not even a question.

Statement Necklaces

They’re bright, they’re bold, and they’re eye catching. Statement necklaces polish an outfit. Whether it’s chunky and colourful, or classic and sparkly, a statement necklace literally makes a statement, and a good one. Confidently rocking your outfit with a statement necklace to top it off is a preppy girl’s dream.


Like many preppy girls already know, the golden rule is: if it doesn’t move, monogram it. Whether it’s your shoulder bag, your necklace, your laptop decals, or even your car. The classic monogram format is first initial, last initial, and lastly, middle initial. To top it off, they’re stylish.

Prints, Stripes, and Plaids

While anyone can rock the prints of their choosing, people with preppy style rock them hard. Stripes are a go-to, and so are plaids. They are perfect transition pieces for spring and fall, when it’s not quite warm enough for tee’s and not cold enough for sweaters. On top of that, pairing plaid or stripes with a solid pant or shoe makes it stand out and look timeless.



It can be on your attire or your accessories. Scalloped shorts are flattering on everyone, and can add flare to even the most plain black dress. Scalloped hems also add visual aesthetic to an outfit. Scalloped bags, clutches, and even shoes are also a perfect accessory that helps tie the preppiest of outfits together.

It’s important to some people to define their style. For myself, I tend to stick to preppy. Being confident in your style is also important; be proud of how you rock your look.


If you’re looking for inspiration when it comes to upping your preppy style, check out the Instagram I share with my best friend, @canadianprepstyle!

Jenna Weishar

Wilfrid Laurier

Fourth year, 20-something year old Psychology and Sociology Major at Wifrid Laurier University. Sorority Girl. Lover of Grey's Anatomy, the Bachelor/Bachelorette, and Sex and the City. Relies heavily on caffeine to get through the day, and wine at night. Follow me on Instagram: @jennaweishar and Twitter: @jennaweishar
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