The Most Versatile Shoe Isn’t What You Think It Is

Versatility.

Most of us look for this trait in everything we buy, especially when it comes to clothes. It always sucks buying something and realizing you can only wear it in limited circumstances.

Also, we always try to buy things that already go with a number of existing items in our wardrobe. Thankfully, if you dress in a fairly timeless manner (which, if you read this website, you probably do), then any relatively traditional piece of menswear will slide into your current rotation fairly seamlessly.

Pretty much any sport coat you buy will go with your oxford shirts, chinos, and loafers.

Pretty much any casual jacket you buy will go with your boots, jeans, and cap.

More than any other category of clothing, shoes need to be the most versatile of all. For one thing, they can be expensive, or relatively more expensive than many of the other items you own. Therefore, you probably don’t own as many pairs of shoes as you do, say, shirts or pants. Given your limited number of shoes, you need to make sure they go well with almost everything else you wear. You wouldn’t want to drop, at the very least, a few hundred dollars on a pair of shoes to only be able to wear them with one outfit.

So, which shoe do you think is the most versatile you can own?

A burgundy pair of open-laced leather shoes (in either plain toe or brogue design), perhaps? These can be worn with chinos, some suits, as well as jeans, at times.

What about a pair of brown loafers? Again, these can be paired with more casual-leaning suits, khaki pants, sport coats, jeans, t-shirts, pretty much anything business-casual.

Both of those are solid choices.

What about a simple, white sneaker? Well, I have already made my opinion known regarding white sneakers.

What if I told you there is a shoe you can wear in pretty much any warm-weather circumstance?

A shoe that is timeless, durable, AND inexpensive?

You’d say I was mad!

But I’m not.

In my opinion, the most versatile shoe you can own is a canvas boat shoe.

Now, I know what you’re saying. “Richard, I clicked on this article and read a whole page of text only for you to tell me that I should wear boat shoes in the spring and summer? I could have gotten that information from the other million menswear sites on the internet. Also, these boat shoes look like they have been beaten to hell!”

All true! But I’m not telling you to simply wear a boat shoe. I am asking you to examine exactly how mind-bendingly useful canvas boat shoes are, as evidenced by this beaten-to-hell pair! And this all comes from personal experience, as does all my advice on this site.

I bought my pair of canvas boat shoes way back in 2013. I had recently become interested in more classic style and already owned a pair of leather Gold Cup Sperry boat shoes. I was in the “Avalanche” stage of my menswear journey so I figured that if one pair of boat shoes was good, then two must be better!

My canvas pair differed from my leather pair, though. My canvas pair, for one thing, had pretty much no insole to speak of. My Gold Cups were like big, soft pillows. The canvas pair was much more bare-bones.

I found that I used them differently than my leather pair. When it was hot, my leather pair would stick to my feet. It was a little bit of a pain slipping them on and off to walk the dog, so I would keep my canvas pair by the door. With time, the canvas softened tremendously to the point where they felt like slippers. I also made sure the laces were super loose so they could be slipped on and off with ease.

Since they were boat shoes, I wore them in fairly casual settings, however I soon realized that they were pretty good at bouncing back and forth between ultra-casual (jeans and t-shirt at the park) to somewhat, kind-sorta nice looking (chinos and polo shirt at brunch).

Interesting, but not exactly shocking. But it was certainly nice to know that I could wear these shoes in nicer situations and not feel out of place.

But I still kept them by the door and used them for dog-walking duty and taking out the garbage. I obviously also wore them to the beach. They are boat shoes, after all.

Then I set up my home gym and everything changed.

My wife and I lived in an apartment at the time (before the boys were born) and the basement floor laundry room had concrete floors. I took advantage of this by setting up a barbell and weight plates so I could do deadlifts without leaving the house.

I never felt like putting on socks and shoes just to go down to the basement, so on went the canvas boat shoes.

You know what? Canvas boat shoes make a pretty excellent weight-lifting shoe. They are almost completely flat and have zero cushioning. It was like lifting barefoot or like wearing a pair of Converse. Also, since they were canvas and not leather, they dried out rapidly and never smelled bad. I did put a dryer sheet in them, just in case, but they never actually needed them. They could also be thrown in the washing machine if situation got desperate.

Wearing my canvas boat shoes while weight-lifting really opened my eyes to how versatile these shoes could be.

I wore my canvas boat shoes for years. When the boys were born, we took pretty frequent trips to the beach. It shouldn’t be a surprise that my canvas boat shoes came with us.

But what DID surprise me was the fact that I could wear my canvas boat shoes while teaching my sons to swim. Since they were so light, being canvas and having no lining or padded insole, I could use them as water-shoes and not weigh myself down as I was swimming along with my kids.

I wouldn’t have been able to do that with my leather Gold Cup Sperrys since they were a little too heavy. However, the canvas boat shoes performed admirably.

Oh, and since they dry quickly, I was able to wear them later that night out to evening drinks with my wife while the in-laws put the boys to bed.

So, let’s recap…

In the morning you slip on one pair of shoes and you can…

Toss on a t-shirt and sweatpants to grab coffee.

Do your morning lifting session.

Play at the park with your kids.

Take them swimming at the beach (and actually swim with your shoes on!).

Go to dinner with your wife.

And do this all without changing your shoes! I think that is pretty much the definition of the word versatile.

Oh, and I forgot to mention… I paid $60 for these. Not only were they super cheap but they are also incredibly durable. The hole on the side of the left shoe is from when I bashed my toe on a piece of jagged steel in a parking lot. If it had not been for the thick canvas of my boat shoe, I would have been in the hospital getting my toe stitched up.

Because of this particular episode, I wouldn’t think twice before wearing these shoes for even some light hiking.

The last bit of praise I can give these shoes is that they are perfect for traveling as they can squish down as flat as a pancake, so they take up minimal space in your luggage.

Really, these really are the perfect warm-weather shoe. Pack them for a long trip and you won’t need to bring any other shoes.

So, as you go about analyzing your warm-weather style this spring and summer, don’t be fooled by all those articles touting the versatility of items using well-worn phrases like “it will take you from work to happy hour” (as if that’s at all difficult).

Take it from me and grab a pair of canvas boat shoes and you’ll be adequately covered until practically the first frost.