Smart Casual Shoes

How Can You Tell If a Shoe Is Smart Casual?

I’ve come up with a simple test to figure out whether a shoe fits the smart casual category. It really comes down to just two questions:

Can it be worn with jeans?

Yes: Move on to the next question.
No: It’s probably too formal (like Oxfords).

Can it also be worn with dress pants?

Yes: You’ve got yourself a smart casual shoe.

No: It’s too casual (think Adidas Stan Smiths or Air Force 1s).

Let’s call it the Roger Test. 🙂

With that in mind, here are my top five smart casual shoe styles—plus great options for every budget.

The best smart casual shoes

Minimal Leather Sneakers

When it comes to leather sneakers, you’ve got your go-to white pair. I also like adding a pair of all-black leather sneakers for extra versatility. Brown options can work too, depending on the outfit, and they can still fit the smart casual look.
If you want the most versatile “smart” sneakers, I recommend sticking to the classics.

 

Loafers

Some consider loafers a spring/summer option, but they can be worn year-round with the right pair of socks, unless you need specific winter footwear. They’re one of the most comfortable and low-maintenance choices for smart casual outfits.

Personally, they’re my favorite type of dress shoe. There’s a wide variety to choose from, ranging from classic penny loafers to more relaxed driving shoes. If you want the “smarter” option, go with a penny loafer. If you want to add a little flair (like I did), horsebit loafers are a great choice.

Derbies or Buchers

When it comes to smart casual shoes, derbies hold a special place. They’re the kind of shoe that can take you almost anywhere: from a wedding to a casual coffee date. If you’re starting with just one pair of dress shoes, derbies are a solid choice.

They’re my dad’s favorite, and I’ve seen him wear all kinds of derby styles for the past 27 years. As I was writing this, I realized he probably wears derbies every single day. 😦

Thinking about my dad reminded me that he often buys Florsheim, and those shoes last him for years. I wasn’t planning to mention the brand, but they’ve definitely earned their place.

Chelsea Boots

Nothing looks better than a pair of Chelsea boots (in my opinion). They’re as functional and stylish as it gets. They were one of the first pins I ever saved on Pinterest. The only real downside is wearing them during the hottest months. Aside from that, they’re pretty much perfect (again, just my opinion).

Leather Chukka Boots With A Clean Design

I was struggling to find a fifth option that felt as solid as the other four for a good “smart” pair of shoes. I went back and forth on whether to include brogues (which are technically just a design), monk straps (which might be too formal), or chukkas (which can lean a bit too casual). In the end, I decided to go with chukka boots.

Just like with minimalist leather sneakers, you’ll want to be selective with chukka boots. To stay on the safe side, go for a leather pair with a clean, minimal design. They add a layer of protection in colder months, and the right pair can be worn with a wide range of pants.

Investing in quality footwear

The advantage of shoes is that you don’t need many pairs. The downside is that if you want real quality, it usually comes at a higher price. I’ve found durable clothing under $30 that lasts for years, but footwear is a whole different game. Still, it’s better to invest in one high-quality pair every now and then than to keep buying cheap ones every few months.