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Preppy Chic For Guys: 5 Style Essentials

The preppy chic aesthetic effortlessly combines timeless classics with pops of color and playfulness, offering a more relaxed version of the old-money style. This blend of sophistication and fun makes the preppy look both versatile and enduring.

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Here are five must-haves to achieve that perfectly preppy look.

Brook Brothers Jacket

1. The Classic Navy Blazer

A perfectly tailored navy blazer is the cornerstone of a preppy wardrobe. This versatile piece can be dressed up or down, making it suitable for various occasions.

For an added touch of authenticity, opt for one with brass buttons lie this one from Brooks Brothers (a classic preppy clothier). This small detail can significantly enhance the overall aesthetic, making your outfit look even more polished and preppy.

Man traveling on yacht. Young sailor on sailing boat. Traveler enjoying sea adventure, freedom. Summer vacation in self isolation, social distance. Wanderlust in covid quarantine. Successful lifestyle

2. Versatile Shirts

When it comes to shirts, you have three quintessential options:

  • The Classic Button-Up Shirt: This shirt is incredibly versatile, perfect for both formal and casual settings. Dress it up for a wedding at Lake Como or dress it down for a day of sailing.
  • The Polo Shirt: An iconic piece that embodies the preppy style, the polo shirt works equally well at the country club or the office. Just remember to pop the collar for that extra preppy flair!
  • The Rugby Shirt: Known for its bold, sporty stripes, the rugby shirt adds a playful touch to your wardrobe. And don’t worry, knowing the rules of the game is strictly optional.

3. Cozy Sweaters

Sweaters are essential for creating cozy New England vibes. Depending on the occasion, you can choose between a fine cashmere sweater for the office or a chunky cable knit for a day at the slopes. Both options offer comfort and style, ensuring you look effortlessly preppy in any setting.

4. Statement Pants

Pants are the true stars of the preppy wardrobe. While khakis are a safe and classic choice, the bolder, the better when it comes to preppy style. Tom Wolfe famously coined the term "go to hell" pants to describe the brightly colored and patterned pants favored in preppy fashion. Here are some standout options:

  • Colorful Chinos: These add a vibrant pop to any outfit.
  • Nantucket Reds: Known for their "guaranteed to fade" look, these pants are a preppy classic.
  • Madras Plaids: Perfect for summer, these pants bring a touch of vintage preppy charm.
  • Embroidered “Critters” Pants: Playfully adorned with motifs like lobsters or sailboats, these pants are sure to make a statement.
Handsome man in daily casual outfit

5. Classic Shoes

No preppy outfit is complete without the right shoes. Here are three timeless options to wrap up your look:

  • Leather Loafers: Ideal for everyday wear, leather loafers are a preppy essential.
  • LL Bean Boots: Perfect for a weekend at your cabin in Vermont, these boots are both functional and stylish.
  • Boat Shoes: Essential for lounging on your yacht or strolling along the waterfront, boat shoes are a must-have for any preppy wardrobe.

Incorporating these five elements into your wardrobe will help you achieve that effortlessly preppy chic look mixing timeless classics with playful elements.