Spiff Up Your Sperry’s: How to Plan a Stylish Boat Outfit

Spiff Up Your Sperry's: How to Plan a Stylish Boat Outfit

Sailing can be a relaxing way to spend an evening or an exciting way to zip across the water. But while sailing is a sport that anyone can enjoy, it comes with its own set of rules and codes that can be confusing for newcomers.

One thing you’ll want to learn is the dress code. You can wear anything sailing; but if you want to fit in, you’ll need to learn to dress like a sailor.

From sailboat dresses to stripes and sweaters, here’s what you need to know to plan a stylish boat outfit to pair with your Sperrys.

Start with Stripes

Nothing says nautical chic quite like a set of stripes. Whether you want a simple, casual outfit for a day out on the water or a preppy ensemble for dinner on the docks, you can’t go wrong with stripes.

A few simple ways to dress up Sperrys with stripes include:

  • A short sleeve white and navy striped tee with white jeans
  • A black and white striped tee with dark blue jeans
  • A long sleeve striped tee tucked into a preppy structured skirt
  • A short sleeve t-shirt dress in navy and white or fun hue, preppy hues like green and pink

Cable Knits Take Sperrys Into Cooler Weather

When most people think of sailing, they picture warm days and shorts with tank tops.

But in New England, spring and fall bring chilly weather and dedicated sailors who still raise their sails. If you’re invited out on the water when temperatures have cooled, skip the shorts and stripes and opt instead for a classic cable knit sweater.

Cable knits in neutral tones like cream or navy look cute and casual with a pair of jeans and your favorite Sperrys.

Add a Vest for In-Between Days

When it isn’t cold enough for a sweater but its too chilly for a t-shirt or even a long-sleeved tee alone, there’s another sailing staple that’ll fill the gap.

A structured puffer vest is a perfect accessory for staying warm on the water. It protects and insults your core, warming you up. But it leaves your arms free of bulk so that you can still chip in and work on the ropes or hoist the sails.

You could opt for a plaid vest over a solid t-shirt for a cute fall look. Or, layer a solid-colored vest over those stripes for a more water-worthy outfit.

If the weather warms up, you can always stuff your vest in your L.L. Bean canvas bag, if you were lucky enough to receive one of the best gifts for boaters.

Go All-American

When you’re shopping for outfits to pair with your Sperrys, choose your colors wisely. Just about any piece can be made to look sailing-ready if you choose the right colors.

One look that always works on the water is an all-American color scheme. Red, white, and blue screams nautical ready. For instance, a navy sweater with white jeans and a bright red rain jacket, paired of course with your leather Sperrys, is a look that’s as chic as it is comfortable.

Pairing Your Boat Outfit With Your Favorite Sperrys

Cruising the coastline in a sailboat is a wonderful way to spend the day. And with your stylish boat outfit and Sperrys, you’ll look chic and ready to hoist the sails and cruise out of the harbor.

Looking for other fashion advice? Head on over to our blog to find other advice for putting together the perfect outfits for every situation.


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