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50 Casual, Non-Preppy Ways To Wear Boat Shoes

Boat shoes are some of the most comfortable shoes you can wear in summer, but it’s easy to write them off as being too preppy for your personal style. We’ve found 50 great outfits with boat shoes that prove that wrong.

It’s hard to find a pair of footwear that’s easier to toss on running out the door than boat shoes. You can slip them right on, they fit securely, and you don’t even need socks. They mold to your feet and become the most comfortable pair of shoes you own. What’s not to like?

The primary misconception people have about boat shoes is that they’re inherently preppy; this isn’t necessarily true. They certainly have a strong history in the prep styles of coastal towns in New England. But that’s like saying Vans can only be worn by skaters or Red Wings by construction workers. It’s entirely possible to wear a pair of Docksiders with Getups that aren’t brightly colored business casual or dressier. If played right, boat shoes might be one of the most versatile summer footwear options in your closet.

Check out the album below for some inspiration on ways to branch away from the preppy connotations of boat shoes.


Like Shane’s looked featured in the top image? Check out our article One Henley, One Pair of Joggers, Three Outfits

one henley one pair of joggers 3 outfits

Some boat shoes we’re digging

boat shoe

Sebago Docksides, $90

boat shoe

Sperry Top-sider, $93

boat shoe

Sebago Spinnaker, $73

boat shoe

Sperry Top-sider, $93

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