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Preppy style in the 1980s was at an all-time excellent high, with Ralph Lauren dominating the fashion aesthetic. The preppy, all-American, Ivy League man signified WASP-y wealth, college education, and jaunts out on the yacht with mom and pop.

It was a clean style, so far from the punk-grunge, hip-hop, and country-mullet styles also huge throughout the decade. If you’re in the mood to get a little preppy and try your hand at this crisp and upbeat look, you’ve come to the right spot, lads. 

The look: bright or pastel polo shirts and sweaters 

The polo shirt is the trademark of the 80s preppy aesthetic, thanks to Ralph Lauren and Lacoste. Polo shirts (with a popped collar) were often in pastel shades such as lilac, lemon, or pale blue, or bright tones of purple, red, or cobalt. 

The true preppy look saw the polo shirt tucked into the waistband of neutral-toned chinos or golfing shorts. But it was the sweater tied around the shoulders that really took the look to new, wholesome heights.

Picture a pink knit sweater tied around the shoulders over a lemon or deep blue polo shirt. Classic. This look is best suited to Summer barbeques, golf tours, or drinkies on the lawn. 

How-to: 

  • Subvert masculine expectations and wear a hot pink polo shirt (a la P. Diddy) with your go-to jeans, but add a grunge component by adding well-loved Docs or combat boots
  • Go full prep with chinos, a belt, a tucked-in pastel polo, and a cotton or wool-knit sweater tied around your shoulders. Extra points for boat shoes or loafers! 
  • Be the Idris Elba or David Beckham of your group and go with a classic deep navy polo, dark blue jeans or chinos, and TOMS, Keds, or Converse 

College jackets and cardigans 

Preppy guys in the 80s repped their colleges with college bomber jackets detailed with leather sleeves, striped collars, and snap-close buttons. Others wore college cardigans with v-necklines, buttons, and contrast cuffs.

The varsity trend has been a preppy staple for decades and has been adopted into different sartorial subcultures such as the modern street-hipster look of our time. 

How-to: 

  • Wear a white button-down shirt and tie with a varsity cardigan buttoned-up over the top, and layered with a smart suit jacket. Polish it off with bone-colored trousers and tan loafers 
  • Take a streetwear approach by pairing a varsity jacket with jeans and Converse 

The look: beige or colored slacks or chinos and leather belts  

Preppy 80s guys rarely wore jeans when they were in full prep mode. Instead, they wore chinos or slacks and leather belts (all the better for tucking a polo into).

Preppy trousers were often in bone, tan, or beige colors, or more out-there shades of pastel pink, deep blue, or rich green. Chinos were often rolled at the hem for a little ankle action and to show off leather boat shoes or loafers. 

How-to: 

  • Copy heartthrob Ryan Gosling by pairing slacks with a knit, polo-style short-sleeved sweater, just tight enough to celebrate your torso 
  • Play with color by wearing berry-toned chinos with a sapphire-blue V-neck sweater (or any color combo that tickles your sartorial senses)
  • Roll up your chinos, throw on a pair of classic boat shoes, and add a thick knit sweater for preppy-meets-fisherman styling 

The look: argyle sweater-vests, tennis shorts, and white Keds 

80s preppy guys living the preppy life always had an argyle sweater-vest or three in their wardrobes. This classic prep print (concentric diamonds in various shades) was commonly worn with short, white tennis shorts and a pair of white Keds. This is an off-duty prep style fit for long Summer days on the court. Or you can go for the smart approach, a good blazer never fails!

How-to: 

  • Layer a white polo shirt with a creamy sweater-vest with blue argyle print, add a pair of white chino-style shorts and white lace-ups
  • If the whole ensemble is far too much (understandable), swap the shorts for neutral-toned chinos and a deep brown belt 
  • Layer your argyle sweater-vest with a tweed jacket or trench coat in Winter, with charcoal wool-knit trousers and shiny leather lace-ups for dapper workwear 

The look: boat shoes 

1980s preppy-guy style extended all the way to the feet, with the quintessential prep shoe styles: the boat shoe or loafer. Boat shoes feature leather laces, raised seams, and leather threading with metal rings along the sides.

They were worn sockless, with chinos, tennis shorts, or the occasional jean. Boat shoes are a perfectly fashionable, if not extremely mature, shoe to wear today. 

How-to: 

  • Forgo the classic deep brown or tan boat shoes for pastel or deep colors such as mint green or rich navy. For example, Pharell Williams wore forest-green boat shoes with denim shorts, a denim jacket, camo-print tee, and chunky necklace 
  • A more casual option is a pair of boat-style tassel loafers, with the leather threading and raised seams of a boat shoe, but the slip-on convenience of a loafer 

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