Have you noticed certain pieces in fashion that have recently ascended beyond having “a moment” to becoming modern-day staples? This includes rugby shirts, blazers, and tennis skirts, to name a few. The stylistic common thread throughout all of these resurged pieces has us wondering, is preppy style coming back? When you look around, the answer is simple–it’s already here.

To celebrate prep’s revival, we’ve teamed up with Sperry and its timeless, yet understated, boat shoes. A required accessory for any prep uniform since 1935, the boat shoe is now trending once again, securing the brand as preppy style's ultimate icon.

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While we can credit the style’s return to celebrities such as Tyler the Creator and David Beckham, who have recently been seen sporting sweaters vests and chinos, it turns out that the return of prep reflects shift in culture–an evolution.

The past two years of on and off solitary confinement, along with its practical consequences like increased solo activities, have forced us to slow down and reflect. And while today's prep style movement may be aesthetically similar to its previous surge in fashion, this modern movement embraces a new era of appreciation–one that moves past cheap thrills of the past into a more thoughtful and intentional future.

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Along with this new perspective on self-expression, comes contemporary adaptions to the market. From street-style brands focusing on more tailored fits to classic prep-renowned brands reentering mainstream media with a modern edge, the way in which the style comes together is truly something new, but Sperry’s position within prep style hasn’t wavered.

Sperry’s latest drops show the brand's eager anticipation for today's new-wave prep, while ongoing collaborations with iconic forces such as John Legend and Rowing Blazers showcase its trendsetting spirit. Other note-worthy collections include Cloud, keeping the classics fresh with modern stylings, and Gold Cup, sourcing luxury materials for premium prep status.

While Sperry’s innovative spirit has taken the boat shoe to new heights, the footwear brand has decided to keep a few elements sacred since its start. True to its heritage, Sperry footwear is still hand-sewn using moccasin construction, with premium technology like its enhanced traction Razor-Cut Wave-Siping™ that made them legendary.

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Whether prep style is popularized or thought to be just another passing trend in fashion history, one thing remains: Sperry revolutionized the genre 87 years ago — and will be here for 87+ more.

Shop the latest from Sperry at sperry.com.

  • Photographer:Louis Browne
  • Stylist:Lisa Li
  • Set Stylist:Kate Leonard
  • Photo Assistant:Dylan Peterson
  • Digital Tech:Running Pixels
  • Wardrobe Assistant:Bre’jon Golden
  • Producer:Justin Trevino
  • Models:Malcolm Evans, LA Model Management & Megan Rodrigues, State Artist Management
  • Producer:Justin Trevino
  • Models:Malcolm Evans, LA Model Management & Megan Rodrigues, State Artist Management

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