Clothes to Wear With Sperrys

Nicky Tavares wears boat shoes with her dress at a movie premiere.

Photo: Ben Gabbe/Getty Images Entertainment/Getty Images

If you're looking for flat shoes that are perfect for any errand, casual event or just to slip on while around the house, Sperrys are a fabulous choice. They come in tons of colors, textures and patterns, but these boat-shoe inspired flats have one thing in common: versatility and a vintage flair. Wear them with jeans and a t-shirt, a cute summer dress, boyfriend jeans, a romper or a chunky sweater.

Jeans and a T-Shirt

Boat shoes like Sperrys look great with your favorite go-to outfit, jeans and a t-shirt. It doesn't matter what style jeans you prefer, Sperry shoes complete your casual and comfortable look and add a just the right amount of preppy to your look.

A Dress

When you're pairing shoes with your cute summer dress, a floral confection, plain tank dress, or other style, Sperrys are a great go-to choice. With the subtly vintage feel of the shoe you will add an interesting flair to your outfit with ease.

Boyfriend Jeans

Boyfriend jeans -- jeans that are a bit baggy and cuffed -- look super cute with Sperrys. You can pair these pants with a tank and cardigan combo, a blouse, or your favorite vintage tee to complete your look. With a bit of your ankle showing between your Sperrys and your pants, your shoes will draw attention and get compliments for sure.


Rompers are adorable and perfect for warmer weather when you don't feel like wearing a skirt or dress. With a floral romper or basic one, Sperrys will show off your effortless style and go so well with your outfit. Compliments on your shoes will be inevitable!


Sperrys aren't just for warmer months, though they may remind you of the beach. You can don them with jeans and an oversized knit sweater for fall or early spring to perfect your cute and casual look.

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