15 Cute Summer Outfits With Sperry’s

Thalita Ferraz // Last Update: July 7, 2023 // 0 Comments

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Hello my wonderful reader, wherever you are in the world!

Not long ago, we spent a few days on the coast in a cute port town. You know, amazing fresh seafood and nautical decor everywhere. It was beautiful and the weather was perfect!

Something you’ll notice in a beach town is that nearly every one of it’s residents owns this one particular shoeㅡand for a good reason too! Any guesses?

Sperry Top-Siders. I personally love my Sperry's for fashion, but they’re actually notorious footwear for sailing and quite functional! Of course, I packed my favorite boat shoes for our trip, but it dawned on me that these really aren’t as common inland.

With that said, I wanted to do a post to give you ideas of cute summer outfits to wear with your Sperry's even if you don’t live at the beach!

1) Romping Around in Rompers and Sperry's

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I love, love, LOVE these two outfits right here! They’re so, “summer-y,” feeling, and it’s awesome that they’ve paired their two different romper outfits with their Sperry’s!

These ladies went the extra mile and matched their hats to their shoes, which helps the color flow through their outfits. A cute straw bag would pair perfectly also!

2) Preppy in Sperry's

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Like I mentioned above, “preppy,” is no stranger to the Sperry Top-Sider agenda but look how cute this outfit is!

Her Sperry loafers look amazing with her khaki shorts and sweater/button up combo! This is a great example of how to dress up a look without needing to put on heels. Loafers scream upper class and business.

Check out my H&M Summer Look outfit, which features denim shorts and a button up that would look amazing with a pair of Sperry Loafers.

3) Nautically Inspired Outfit with Sperry's

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Remember how I said Sperry's were known as Boat Shoes? That is because of the sole, which is designed to maintain traction on slick surfaces- such as on a wet or icy boat deck without harming the deck.

I had to share a look, where the shoes were not only perfect fashion wise but they were also functional!

Horizontal stripes have always been a player in the nautical world. Her striped sleeveless shirt looks amazing with her crisp white pants (which are also functional because white helps keep you cool).

She of course could have worn a cute pair of wedges or sandals with this look, but out on a boat? No way! Her Sperry Top-Siders are keeping her aboard the boat and looking fabulous.

4) Spring-y in Sperry Flats

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Pretend this outfit excluded the jacket, because during the summer we of course don’t usually need them over our dresses. I wanted to share because it is a great way to wear Sperry flats fashionably with a dress.  Who knows, maybe she gets cold in the rain.

This is a good example of a different type of Sperry, where it’s more like a flat than a loafer. Also a look that doesn’t make you look like you’re going to the beach or out on a boat!

5) Shorts and Blue Sperry's

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Keeping with traditional nautical hues, Sperry’s often put out shoes in shades of blue. They’re perfect, aren’t they?

This look is a really easy way to wear Sperry’s on a normal and casual basis. There’s nothing fancy about her white tee, denim shorts, belt, or hat. She’s just out there living her best life in a great pair of shoes.

6) Sperry Sneakers

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Sperry’s come in a plethora of styles, colors, and even patterns. This outfit shows a cute pair of Sperry Sneakers that look great with her cardigan, t-shirt, and shorts. 

Sperry Top-Siders that embrace the Loafer look is commonly seen in a more, “preppy,” street style, so the sneakers are a fun option to be more casual while still looking classy.

7) Sperry's and Dress

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This is another great display of Sperry Sneakers but worn with a t-shirt dress!

It’s such a simple look. Striped dress, with a button up wrapped around her waist and sneakers. It pulls together nicely, and is truly effortless.

Check out my Mini Blue Dress outfit which is a great example of a dress that would work perfectly with a pair of Sperry sneakers, flats, or loafers!

8) Sperry's and a Skirt

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No surprise here that these Sperry loafers look amazing with the vibrant skirt and striped shirt in this look. It’s a great layer being added with the jacket, which makes your look more versatile and seasonally friendly.

9) Printed Sperry's

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I love that this look gives an alternative to the beachy vibes. These Sperry’s step away from the shore with a fun animal print on them, which adds a little flare to this simple black pant white tank outfit. Plus, who can deny a great animal print?

10) Street Sperry's

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Another fun alternative to the nautical-ness Sperry’s have to offer, this outfit is super cute and much more edgy! 

Her Sperry's pull into the same hue as her cropped long sleeve, which could easily be substituted for a cropped tank or short sleeve for those warmer days.

All of it looks amazing with her high waisted shorts. Imagine how amazing these particular Sperry's would look with my High Waisted Suspender Shorts outfit! Yes please!

11) Sperry Business

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This is one of those looks that is right up my alley, I love wearing clothes that would usually be considered business in a casual setting, or at least outside of work.

This pair of Sperry Loafers has that traditional loafer look with the tassels across the top. She’s wearing a blazer over a white shirt and vinyl skirt. Check out my Gray Plaid Blazer outfit for some more outfit inspiration that would look amazing with a pair of loafers like these!

12) Sperry Boots

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Remember I said earlier that Sperry’s came in a variety? Love these Sperry leather boots with me! Another pair that is less beach and more city that would look amazing with work attire, denim pants, and leggings, dresses, and (as we can clearly see here) skirts!

Imagine how cute these boots would look with an outfit like my Dalmatian Denim set!

13) Sperry Duck Boots

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I’m a little unsure if this outfit is meant for cold weather and she’s really brave, or maybe it’s just not that cold and she’s really tough. Either way, check out these duck boots!

The duck boots are fun because they’re a combination of rubber for a waterproof element, and either canvas or leather. They also come in a variety of colors, so it makes for some extra shoe options.

These boots could easily replace combat boots in your summer outfits and be used during the winter to keep your feet dry on those snowy winter days!

14) Classic Sperry

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I really do love a good graphic tee outfit. This is one of those that is just… a “duh” moment for me. It’s so easy to throw a graphic tee on with a pair of high waisted denim shorts. Adding the hat and jacket is fun.

She could easily have worn a pair of regular sneakers here, a pair of cute slip on Vans, or similar. Having these classic Sperry’s almost gives this outfit a touch of masculinity, if that makes sense. Whatever it is, it’s awesome and this look is rocking the casual classic Sperry!

15) Sperry Sneakers and a Dress

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I know I shared a dress outfit already, but this one is so cute with the polkadot red dress! This is a different color of the Sperry sneakers that you saw in one of the outfits above, and they’re just as awesome.

I should also note that these don’t have to be worn with short dresses! They’d look great with a longer skirt or dress, such as this Yellow Polka Dot Matching Set.

Being so far from the ocean is a bummer, but that doesn’t mean we can’t enjoy nautical fashion! Of course, after checking out these outfits, we can see that Sperry’s are amazing and aren’t limited to just nautical wear.

What do you think about these summer outfits to wear with Sperry's? Sperry’s are so versatile, and look great with cooler weather outfits too. Perhaps when the seasons change I’ll do a post on wearing Sperry's during the winter. Do you have any requests? Tell me in the comments below!

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