The preppy look traditionally referred to the style of kids attending preparatory schools in the US. Its roots go back to the 1920s when wealthy Americans began sending their children to the best private schools they could. The uniforms of these schools tended to be highly influenced by traditional English dress codes. Over time, this evolved into the preppy look we know and love today!
The preppy look incorporates pieces such as Oxford shirts, brogues, plaid skirts, pinafore dresses, blazers, and golf-wear-inspired garments. And the eyewear is an essential element of the preppy look! Thick-rimmed rectangular glasses, Wayfarers, and simple round-framed spectacles are all staples of this distinctive style.
Preppiest Movies of All Time
Annie Hall (1977)
Diane Keaton, star of Annie Hall, was dressed by Ralph Lauren for this movie – and Ralph Lauren is well-known for being the ultimate preppy brand. Black vests, printed ties, tailored white shirts, tan pants, and fedora hats delivered perfect preppy styling.
Dead Poets Society (1989)
In this seminal 80s flick, a group of boys fights back against the status quo, led by their unconventional teacher, played by Robin Williams. Why’s it so preppy? The sheer volume of Argyll sweaters, Varsity sweatshirts, tweed blazers, and neckties means it more than makes the grade as one of the preppiest movies of all time.
Clueless (1995)
This movie was filmed in just forty days; the writers actually sat in on classes at a Beverly Hills High School to get a real idea of how the students spoke to each other! And its preppy fashion credentials? An impressive 53 different types of plaid and tartan were worn in the course of the movie. Enough said.
The Talented Mr. Ripley (1999)
There is a plethora of corduroy jackets, cashmere turtlenecks, brogues, and striped scarves in this movie starring Matt Damon and Jude Law. Interestingly, we can see the journey of the main character reflected in the changing style of clothes he wears throughout the film as he becomes increasingly obsessed with effectively becoming someone else.
Legally Blonde (2001)
Everyone loves this movie starring Reese Witherspoon, who plays the preppy character of Elle, who dreams of becoming a lawyer. New England’s preppy style is perfectly epitomized by Elle’s sartorial choices – knitted cardigans, purple plaid ties, and mini tan-colored and plaid skirts reflect her sweet and stylish character.
Square-Shaped Wayfarers
One of the key preppy eyewear styles is the square-shaped Wayfarer, with either black or tortoiseshell frames. In terms of design, think classic and simple. This style of glasses is elegant and chic and looks great with all types of outfits.
It’s important to take into account your face shape when choosing glasses to find the most flattering type of frame. Square-shaped Wayfarers usually look best on those with round or oval face shapes. Those with other face shapes can still rock the style: try square-shaped wayfarers with a subtly curved frame or those with clear frames for a flattering look.
What to Wear Them With
For the ultimate preppy look, wear your square-shared Wayfarers with a layered shirt and pullover, a black pleated skirt, and a pair of flat pumps. Add a chiffon scarf and a pair of pearl stud earrings to complete your ensemble!
Simple Round Spectacles
Simple, classic round glasses have also long been a staple of the preppy look. This style looks particularly fabulous on those with square, diamond, or heart-shaped faces. Again, choose either clear frames or those in black, brown, tortoiseshell, or gold. Avoid oversized round styles to get the most authentic preppy look.
This type of eyewear can add easy elegance to most outfits and can take you from day to night- simply switch up your accessories as necessary!
What to Wear Them With
Fully embrace the preppy look by pairing your round glasses with a tailored white shirt and navy chinos or skirt, and add a fitted blazer and a pair of brown brogues. Add some fun to your ensemble with a bow tie, a beret, or a similar accessory to express your personality.
Thick-Rimmed Rectangular Framed Glasses
Another piece of standard preppy eyewear, the thick-framed, rectangular-shaped glasses are probably the most ‘traditional’ preppy specs. This style can be worn by both men and women and look best on people with oval, round, or heart-shaped faces. When choosing a pair, ensure that the frames aren’t too large to avoid overwhelming your features and looking too severe.
What to Wear Them With
Try layering a tunic over an oxford shirt and wearing it with a pair of tan cargo pants. Alternatively, team your preppy glasses with a polo shirt, jeans, and smart pair of loafers. When it comes to accessories, a stack of bead or pearl bracelets is just the thing.
Making the Preppy Look Work for You
The best thing about the preppy look is that it’s got plenty of flex in it. Have fun with it, and mold
the style to suit your personality and unique aesthetic. For example, incorporate a couple of preppy pieces, such as an Oxford shirt, brogues, and pair of Wayfarers, with other items from your wardrobe, for a new twist on the preppy vibe.
