How to Dress With Boat Shoes

by Lane Cummings ; Updated September 28, 2017

Paul Sperry invented what we know to be \"boat shoes\" in 1935. According to Sperry's official website, \"Paul Sperry, inspired by his dog Prince's ability to run nimbly over ice and snow, used a pen knife to cut siping into the outsole of a rubber sneaker.\" Boat shoes are similar to loafers, but are sportier, offer a no-slip grip and give you more pairing options when it comes to dressing. Traditionally made of brown leather, with a raw hide lace woven throughout the perimeter of the shoe, they now come in more colors such as blue, dark green or white.

Items you will need

  • Boat shoes
  • Appropriate attire
Step 1

Wear any type of khakis, chinos, jeans, shorts or cargo pants with boat shoes. Boat shoes are a type of footwear designed for water enthusiasts; they're extremely sporty shoes that are sometimes even compared to moccasins. Thus, they look good with very sporty to slightly sporty pants. Do not wear boat shoes with dress pants.

Step 2

Wear any kind of T-shirt, long-sleeved shirt, sweater, sweatshirt, hoodie, or thermal jacket with boat shoes. All of these clothes lean on the more casual side of the wardrobe. Boat shoe complement such a casual look.

Step 3

Wear button-down shirts, sports jackets, sweater vests and ties with boat shoes only if you want to give your look a more casual \"dressed-down\" appearance. For example, wear boat shoes on a date with a button-down shirt and sports coat so that you look nice, but not too nice.


  • Women can follow the above advice for dressing with boat shoes, with garments that are made for women, such as jeans, khakis, shorts and cargo pants. Women can also wear summer dresses with boat shoes, but they should be of the casual variety, preferably made of cotton.


  • Never, ever wear socks with boat shoes.


Photo Credits

  • Jupiterimages/ Images

About the Author

Lane Cummings is originally from New York City. She attended the High School of Performing Arts in dance before receiving her Bachelor of Arts in literature and her Master of Arts in Russian literature at the University of Chicago. She has lived in St. Petersburg, Russia, where she lectured and studied Russian. She began writing professionally in 2004 for the "St. Petersburg Times."