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.

50 Casual, Non-Preppy Ways To Wear Boat Shoes

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 look 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

Brad is a full-time student at Temple University in Philadelphia, PA. He is a consistent contributor to numerous fashion communities, and specializes in long-form composition. Above all else, he is currently stressed out of his mind. Feel free to contact him on Reddit for suggestions, inspiration, and pleasant conversation!


  • Reply July 11, 2018

    Jake Baken

    Great post! I always have such a hard time finding shoes to wear with my jeans. Finding something that is casual, but still “adult” is always tough for me.

    • Reply July 11, 2018


      Thanks! Yeah that’s definitely an annoying problem.

  • Reply July 11, 2018

    Serafin Nunez

    So always sockless?

  • Reply July 14, 2018

    Alfred R.

    Hey, this is a great post, it has helped me a lot with some ideas, but I was thinking that for robust guys like myself they don’t always looks that good, is there a chance that you can do a guide for big guys like myself? (robust is like wide back, long arms, either chubby or muscular kind)

  • Reply July 20, 2018


    Awesome post!! I must say you have listed some amazing collection of Boat shoes. I love wearing the, they are so comfortable and easy on the feet.

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