How To Wear Sperrys The Right Way (For Men & Women)

We only feature products that we hope you will love. We may earn a commission if you decide to make a purchase through our links, at no cost to you.  

Boat shoes are a wardrobe staple for a chic, classy look! In this guide, we’ll explore what to wear with Sperrys for both women and men. 

Boat shoes are a time-honored summer staple that has been around for decades. The popularity of boat shoes is undeniable, and they continue to be the shoe of choice for men, women, and children alike for a casual outfit with a nautical look. What do you wear with boat shoes? There are many possible combinations – this blog post will talk about that!


What Are Boat Shoes Or Sperrys?


The term “boat shoe” can be used to describe a type of low-heeled, casual shoe with a nautical style. Boat shoes are typically made from leather and designed in such a way that they resemble the deck shoes worn by sailors. 


Brown leather boat shoes

Get these boat shoes at Sperry


Boat shoes became popular when they were introduced by Sperry Top-Siders in 1935; since then, boat shoes have been adopted as part of many summer wardrobes.

While there’s no wrong way to wear this pair of shoes, there’s only one classic rule of thumb: you must wear no-show socks. For a sockless look, you can wear invisible socks (or foot socks) along with your favorite boat shoes.

Keep in mind that although boat shoes are designed to be worn on a boat (hence their rubber soles), they’re not meant to get wet especially if they’re made of leather. But with proper care, your iconic boat shoe will last you for many years to come.

Boat shoes are very classy footwear that adds a touch of elegance and sophistication when worn. In this style guide, we will discuss what clothes to wear with boat shoes – both for men and women.


What To Wear With Sperrys For Women

1. Jeans


What To Wear With Sperrys: Distressed mom jeans

Get these jeans at Lulus


All jeans are alright to pair with boat shoes, but for a more laid-back, casual feel, we recommend mom jeans. Mom jeans are not too constricting on the legs, therefore giving you space to move around freely. To complete your casual look, wear an oversized white button-up top, and tie the ends in front of your waist to give it style.

Dark-wash skinny jeans are also another great option to wear with boating shoes – they look classic and never go out of style. But if want to opt for a nautical look, white pants (or white jeans) and a striped top (preferably a long sleeve shirt) would be a perfect pair.


2. Leggings


What To Wear With Sperrys: Black mono leggings

Get these leggings at Lulus


If you want to go the extra mile and look stylish, leggings are another great choice. Leggings can be paired with boating shoes just like jeans – they’re both casual staples that pair well together for a chic athleisure look. Sperry topsiders paired with your favorite tee and leggings are the perfect outfit for casual wear or everyday wear.


3. Midi Skirt


Printed midi skirt with black crop top

Get this midi skirt at Hello Molly


Midi skirts are a great choice for women who want to look classy and chic. Pair your boat shoes with a cute cami top, a pencil-style midi skirt, and the boat shoes of your choice: now you’ve got an ultra-feminine look that’s perfect for a day out on the yacht club.

Midi skirts can be worn both in warmer weather or for the fall season.


4. Denim Shorts


What To Wear With Sperrys: Denim shorts

Get these shorts at Lulus


For an ultimate summer look, denim shorts are another great option for women. Pair your boat shoes with a cute tank top and some short denim cutoffs – it’s an effortlessly stylish outfit that’s perfect for the beach or even just hanging out at home.


5. Dress


What To Wear With Sperrys: Sage green bustier skater dress

Get this dress on Lulus


If you want to look extra-feminine, why not pair your boat shoes with casual dresses? A cute casual skater dress is the perfect choice – it’s classy and feminine at the same time, making it the perfect outfit for a relaxed picnic date or an elegant look for dinner parties aboard a yacht.

It’s also a great choice if you’re going for a preppy look. Wear any boating shoe of your choice, then maybe throw on a denim jacket for an edgy twist. 


6. Wide-Leg Pants


Striped wide leg pants

Get these wide-leg pants at Lulus


Wide-leg pants are a great way to dress up and look stylish. Pair your brown boat shoes with wide-leg pants like striped or navy trousers, then add on a simple top for extra style points!


What To Wear With Sperrys For Men

1. Jeans


What To Wear With Sperrys: Casual jeans

Get these pants at J.Crew


Jeans never go out of style; plus, you can wear them with almost anything! You can pair any boating shoe choice that you like with jeans and be comfortable while looking stylish at the same time.

Jeans are one of the most common items of clothing worn by men in America today; they are versatile enough to be paired with any type of shoe imaginable! You can wear your pair of boat shoes with jeans regardless if you’re dressing up nice or going for a casual vibe.

Jeans are a classic choice for men, so pairing your boat shoes with jeans is the perfect way to show off your laid-back style. If you prefer something more formal, then dark-wash slim-fit slacks paired with some dressy brown leather boat shoes will do just fine – it’s what we’d call smart casual!


2. Chinos


White chinos with striped polo shirt

Get these chinos at J.Crew


Don’t want to get too casual? No problem! Just choose chinos instead of denim jeans and put together an outfit that’s perfect for a sunny day out on the boat deck. Chinos are a great choice for boat shoes because they’re not too casual or dressy.

Chinos can be paired with any type of boating shoe to create an outfit that’s appropriate in almost all types of settings – whether it’s at work, school, church, or even when you go out for drinks! Chinos look great with both formal and informal styles so pairing them with your favorite pair of Sperry boat shoes is easy peasy lemon squeezy.

If chinos are not your personal preference but you still want to look smart-casual, you can also wear boat shoes with khaki pants and a striped polo shirt.


3. Dock Shorts


Navy dock shorts

Get these dock shorts at J.Crew


Dock shorts are a great look for summer or on casual Fridays! If you want to look laid back and casual, then wearing your Sperry shoes with dock shorts is perfect.

Dock shorts especially pair well with a white shirt or a button-up polo – this just adds a nice touch to complete your outfit. You can also opt for chino shorts if you want. Don’t forget that boating shoes come in different colors besides brown either – so feel free to be creative by adding color into your outfit as well!

We hope you found this style guide helpful! If you’re still looking for more fashion inspiration and tips, check the posts down below.


Get More Fashion Ideas

Attending A Boat Party? Here’s The Dos & Don’ts You Don’t Want To Miss

How To Pick The Perfect Shoe Color To Wear With A Yellow Dress

What To Wear (And Not To Wear) To A Celebration of Life Ceremony

Browse All Fashion Posts

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.