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Preppy style is associated with the higher class, Ivy League universities, expensive prep schools, Hamptons holidays, spendy skiing vacations, and all-round clean aesthetics.

Think polo shirts, slacks, chinos, argyle sweaters, cardigans tied around the shoulders, knee-high socks, nautical stripes, crisp shirts, plaid skirts, and brogues. 

The preppie look was big in the eighties, as evident on the runways and the big screens of the decade. 1980s preppy style is a fun fashion aesthetic to emulate in 2020, and we’ve found the best ways to “get the prep” today. 

Slacks or jeans, a pastel polo, and cardigan or sweater

Celebrity inspiration: in the 1980s, Calvin Klein was a huge name in the fashion world, with his jeans and briefs gracing the bodies of celebrities and the “normal” folk of the world. Some of his campaigns and collections had a distinct preppy vibe to counter the super-sexy underwear and toned bodies.

However, Ralph Lauren was and still is the ultimate preppy brand, with 1980s collections featuring bone-colored slacks, pastel polos, blazers, and boat shoes. The models were tanned and windswept beauties you imagine to be named Bunny and Chaunce off for a spot to have drinkies with Kitty and Chip. 

One of the most inspiring photos of 1980s preppy fashion shows Brooke Shields dressed in a pink polo, a yellow sweater over her shoulders, and high-waisted dark blue jeans. Her big, curly hair and sultry makeup made her the ultimate all-American girl. 

This look reminds us of days on the golf course, Summer barbeques, or strolling the grounds of a tree-lined university. In real life, it could be a great look for weekend markets, work casual Fridays, and afternoon drinks on the lawn. 

How-to: 

  • If polo shirts are just not for you, swap it out for a pastel or candy-colored crew-neck tee or cotton shirt tucked into dark blue kick-flare jeans
  • Pick a contrast-hue sweater or cardigan and tie around your shoulders 
  • Pair with black Chelsea boots under your boot-cut jeans, or smart white tennis shoes 
  • Edge-up the look by picking distressed skinny jeans and studded leather brogues worn with your sensible blouse and sweater (party on the bottom, preppy on the top)

Shirt-dress with cable-knit cardigan 

Celebrity inspiration: Reese Witherspoon’s timeless everyday style is classic preppy mixed with Southern glamour. Reese takes classic 80s-style preppiness and brings it into the modern era seamlessly. She rocks white jeans, tennis shorts, dark blue jeans and flats, all with her signature item: the preppy button-down shirt in crisp white or pale blue. 

She’s also a fan of the clean shirt dress, cinched at the waist and worn with flats or wedges. This is a sweet little ensemble for more casual workplaces, weekend markets and brunching, and hazy afternoon drinks. 

Reese is also often snapped with a tote slung over her arm, fresh hair, and minimal-yet-curated accessories such as sunglasses and a leather belt. Reese is our Southern-meets-California preppy queen. 

How-to: 

  • Find a denim or chambray shirt-dress with a hemline that sits above or below the knee (mid-knee-skimming hemlines tend to be unflattering) with a self-tie, or cinch with a braided tan belt
  • Pair your shirt dress with leather Chelsea boots or moto boots, or strappy wedges for Spring (and a little extra height)
  • Deconstruct the look by pairing an oversized bright white linen shirt dress with tanned suede Western-style boots and a tote over your shoulder 
  • Up-the-prep with a nautical-style striped sweater worn over your shirt dress with the shirt collar exposed, or with the sleeves tied jauntily round your neck

Pastel Bermuda shorts with a cotton shirt, cardigan around the shoulders, and visor 

Celebrity inspiration: Emily Gilmore from ‘Gilmore Girls’ is the ultimate old-school preppy baby boomer. The senior Gilmore woman was most often seen in smart skirt suits or a gold-buttoned collarless jacket and neat slacks. 

However, on a few occasions she was seen in a more preppy-casual attire of bermuda shorts, a pastel shirt (tucked in), a cardigan worn around the shoulders, and a visor. 

This is the perfect outfit for a day on the golf course, touring college towns on foot, or running weekend errands. However, if you’re not living in a fancy fictional world, it’s a great costume idea for an 80s/90s preppy party. Or, adjust it to make it edgier and less refined for 2020 casual styling. 

How-to: 

  • Find a pair of high-waisted denim “skorts” or culottes and pair with a plain marle grey tee or graphic long-sleeved tee
  • Get your hands on some woven huarache flats for authentic 80s styling, or go full golf-course prep with plain white trainers or Keds
  • Search for a college-style cardigan or jacket with contrast trim on the lapel, cuffs, and pockets and sling it around your shoulders 

 Pleated miniskirt, sleeveless Argyle sweater, knee socks, and Keds

Celebrity inspiration: Rachel Green’s style on early season ‘Friends’ has become somewhat of a reference point for 2020 casual styling ideas. 

Her style had some overhangs from the 80s preppy scene mixed with 90s sweet-grunge, for example; shirts tied at the waist, mini skirts and cute shoes, and her USA long-sleeved top (OG fans will remember).

However, her most preppy look was a tartan pleated mini, knee-high socks, and a high-neck crop sweater.  

This is arguably one of Rach’s most iconic and recreated looks of the early seasons, and for good reason, she looked so darn cute! This is an ideal look for a Friends-themed costume party, or a 1980s preppy party. 

How-to: 

  • If you’re past your ultra-mini phase, opt for a tartan midi-skirt with a pencil silhouette and high waist and pair with a cropped long-sleeved boxy-style sweater
  • Pair an a-line miniskirt with an argyle sweater and shirt with the collar peeking over the sweater neckline
  • If you prefer full tights as opposed to socks, there are some great stockings on the market that feature a knee-high-style illusion with opacity to or over the knee, with sheerness at the thigh 

Country-chic with tan trousers, a crisp white shirt, and tweed blazer 

Celebrity inspiration: in the 1980s, Ralph Lauren was the ultimate preppy brand (and still is). Campaigns showed men in creamy-colored trousers, tan brogues, ties, and navy blazers, or all-white tennis outfits with shorts and polos. 

The women were dressed in tan trousers, tucked-in white shirts and tan belts. Or smart Ivy-style with trench coats, tweed blazers, neckties, and all-beige outfits.

The Ralph Lauren preppy look is fused with country, equestrian hints, with all-American overtones. You can easily translate this look into 2020, as it’s timelessly classy and very versatile.

How-to: 

  • Find a pair of cream or tan high-waisted, pleated trousers and wear with a tan leather belt and white linen blouse tucked in. Rough-up the look by rolling up the sleeves and unbuttoning the top few buttons for a low V effect 
  • Pair with a navy cardigan worn undone for casual wear, or an earthy-toned tweed or wool blazer 
  • Streamline the look by swapping out pleated trousers for slimline cream or tan denim jeans in a straight or boot-cut 
  • Swap out the blazer for a v-neck cable-knit or argyle sweater vest worn over a roomy linen blouse 
  • Tan or chocolate-brown Chelsea boots or tan leather brogues are a classic footwear choice for smartwear, or leather slip-on moccasins for a more casual (but still classy) ensemble 
  • For the true 80s Ralph Lauren preppy-country aesthetic, wear your hair out and lusciously lifted at the roots, with soft brown kohl on the eyes, deep nude lips, and a golden tan if your complexion allows 

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