How to Wear Sperry Boots

Last updated on January 29th, 2022

A classic American brand, Sperry makes some of the best boots on the market. Sperry boots are a classic style that can be dressed up or down. They are perfect for colder weather and can be worn with various outfits.

While they are popular among boat enthusiasts, their stylish and durable designs make them a perfect option for everyday wear, too. Here are some tips on how to wear Sperry boots in style.

How to Wear Sperry Boots

10 Reasons Why You Should Wear Sperry Boots

1. Great for Outdoor Fall Activities

Sperry boots help keep your feet cozy and comfortable during outdoor fall activities, such as apple picking or visiting a pumpkin patch.

2. Comfort

Sperry boots are made with the highest quality materials and with your comfort in mind

3. Affordable

Sperry boots come at a range of prices to help you find what you’re looking for without breaking the bank.

4. Great for Casual Wear

Speakers can be worn for just about anything, from running errands to going out with friends. They’ll quickly become your go-to casual shoe!

5. Waterproof and Weather-Resistant

Sperry boots are designed with seam-sealed waterproof technology to keep your feet dry.

Sperry Boots Are Waterproof

6. Ageless and Timeless Styles

Sperry boots are designed with timeless styles that will never go out of fashion.

7. Quality Craftsmanship

Sperry boots are made with the highest quality materials to ensure they won’t fade or lose their shape

8. Ready for Any Weather

Sperry boots are built with weather-resistant technology to keep your feet dry and cozy, whether it’s raining or snowing.

9. Comfort Technology

The inside of all Sperry boots contain top-quality memory foam for added comfort.

10. Great for Everyday Wear

Sperry boots are a great everyday shoe because they go with almost any outfit and help keep your feet comfortable all day long!

You Can Check It Out to Can You Wear Boots With Joggers

7 Ways on How to Wear Sperry Boots

1. Casual Weekend Look      

Add a sporty element to your casual ensemble by wearing Sperry boots. The elevated look pairs well with slim chinos and a long sleeve tee. Finish the outfit off with a marled sweater.

2. Dressy Look       

Add polished appeal to your dressier look by wearing Sperry boots. The elevated addition adds polish to denim, or go for all-out style points by pairing them with slim jeans and a slim-fit blazer.

Wearing Sperry Boots

3. Creative Rendering             

Creative types can dress up their streetwear looks with Sperry boots. The elevated touch pairs well with dark selvage denim, black joggers, and a long sleeve tee. Finish by adding statement accessories like a fedora and camera bag.

4. Country Club Casual       

Pair your Sperry boots with chinos and a button-down shirt for a country club casual look. The elevated touch adds style to classic menswear staples. To give the ensemble a more playful flair, add unique accessories like tortoiseshell sunglasses.

5. Preppy Look       

To achieve a classically preppy look, wear Sperry boots with chinos and a polo. The elevated touch gives the style an edge, making it perfect for casual Fridays at the office or casual days at school. Finish off by adding statement accessories like cufflinks and aviators.

6. Street Look               

Trendy types can get in on the Sperry boot trend by pairing them with joggers and a long sleeve tee. The elevated touch gives your look an air of cool, making it perfect for weekend brunches and shopping trips. Finish off by adding statement accessories like hoop earrings and a cross-body bag.

7. More Dressy Look               

Pair them with slim chinos and a blazer for a more dressy take on the Sperry boot trend. The elevated touch gives your look an air of polished refinement. Finish off by adding statement accessories like sunglasses and cufflinks.

You Can Check It Out to Deflate Normatec Boots

Some Tips and Suggestions

Here are some tips and suggestions on how to wear sperry boots.

  1. Sperry boots should be worn with a little bit of snugness. They should never feel uncomfortably tight but bearing in mind that the leather will stretch and conform to your foot after repeated wearings, you don’t want them too loose from the start.
  2. When lacing your Sperry’s, take care not to lace them too tightly. A good fitting boot will have enough room in the forefoot area so that you can wiggle your toes and even take off your footwear without untying them first; any more tension than this, and the boots are probably too small for you.
  3. Sperry boots look best when worn with a skinny or low profile trouser leg.
  4. The original type of factory lacing on the Authentic Original is a more traditional round braid; however, if you prefer, you can have a flat lace put in as well. If you do not want to re-lace your boots, we can add a zipper to the inside of your boot (zipper on the left in the photo, traditional laces on the right).
  5. Feel free to ask for a half-size smaller if you want a tight fit.
  6. Sperry boat shoes are meant to be worn barefoot when onboard our boats. They also look great paired with no-show socks in colder weather combined with jeans, cords, or even shorts when the water is cold!
  7. A boot jack is the easiest way of getting your Sperry footwear off and on without damaging or distorting them.
Sperry Boots Look Best

Things to Consider When Wearing Sperry Boots

  1. The lighter-colored leather is very soft and sensitive,  meaning it scratches easily.   Do not rub your boots against rough surfaces, or they will quickly get scratched and scuffed. If you do happen to scratch them, clean the area with a damp cloth immediately to avoid the color from changing.
  2. Since they are made of natural materials, you must expect each pair to behave differently than another. Every leather reacts according to the person wearing it.
  3. Not all Sperry boots are created equal, especially if they’re made from different suppliers in different countries. The thinner the leather is, the more supple and flexible it. Some boots might not fit exactly as they should. It’s more of a personal preference than anything else.
  4. When you first receive your boots, make sure to give them some time before wearing them out. Please make sure they are comfortable and don’t pinch anywhere or rub your skin. If a breaking-in period is needed, it’s best not to wear them out before the leather has molded to your feet.
  5. Since leather products are naturally porous, water may affect the color and texture of your boots. If you plan on wearing them in wet conditions, make sure to clean them afterward with a damp cloth or brush to remove dirt that was trapped inside. If any salt or chemicals are still present, make sure to clean them again.
  6. To avoid color transfer, be careful not to rub the leather against light-colored clothing or vice versa. Instead, use a damp cloth to clean the affected area since the color transfer is permanent.

What Are the Best Sperry Boots for Winter?

The perfect touch to your winter wardrobe is Sperry boots. Featured in countless fall fashion shows and worn by practically every stylish celebrity, these ankle-height footwear classics can instantly kick up the cool factor of whatever you’re wearing. Like Vans sneakers or American Apparel leggings, Sperry boots are a staple for many people’s winter wardrobes.

What Are the Best Sperry Boots for College?

Many college campuses get hit with winter rain, sleet, and snow. If you’re attending class this winter, but don’t want to subject your feet to cold weather or wet conditions, then Sperry boots are a must-have. These boots feature a variety of styles and colors, including boots specifically designed to keep your feet warm and dry.

How to Wear Sperry Boots With Jeans?

We’d recommend dark blue jeans if you’re wearing brown leather boots. And if the boots are black, go with a pair of black denim. If they both come in lighter shades, wear either color. But, again, it’s a matter of personal preference. The goal is to have your legwear be predominantly one color with just a pop of another.

Wear Sperry Boots With Jeans

Is It Okay to Wear Moccasins With Sperry Boots?

If the moccasins and Sperry boots are of the same color, then it’s perfectly fine to wear them together. However, if they come in different colors, pair lighter-colored moccasins with black, brown, or white boots. Just don’t wear black moccasins with dark leather Sperrys; it’ll make it look like you’re wearing snow.

How to Wear Sperry Boat Shoes?

Dark denim jeans are always great with boat shoes. If you’re the old school type, tuck in your polo shirt or fitted tee. You can also rock casual or formal shorts with them; just make sure it’s not too short to see the socks peeking out of your shoes.

Sperry Top-Siders are probably one of the most popular casual shoes today. They’re boat shoes, so they give off a casual vibe, but Sperry Top-Siders can also be worn in formal settings. So it depends on how you wear them and what clothes to make them appropriate for the occasion.


Sperry boots are perfect for the fall and winter months. They look great with jeans, skirts, or dresses, so you can wear them to work or during your downtime. When it comes time to break out these stylish shoes, make sure that you’re wearing socks!

It may seem like a small detail, but they will freeze during an autumn walk if you don’t cover up those feet in warm woolen socks.

We recommend wearing them with your favorite dress or skirt for a night out on the town for those who want more than just basics.

No matter what you decide to do, it’s always best to wear them during cold weather, so be sure to stock up now! We hope this blog post on how to wear sperry boots has been helpful. If you have any questions or want to know more, then feel free to comment below!

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