As fashion trends keep gearing towards casual wear, many guys out there are forgetting to invest in a pair of dress shoes. And, if there’s one thing a modern gentleman shouldn’t miss, it’s a nice pair of dress shoes.

Even with the casual trend, dress shoes remain a wardrobe staple. Since you’ll never know when you’ll be invited to a fancy occasion, it’s best if you’re already prepared if ever that happens.

If this is your first time buying a pair of dress shoes, buckle up. There’s a lot more you need to know about dress shoes than you think. Because, unlike sneakers, dress shoes have certain styles that match different functions and occasions. In fact, you’ve got more than a handful of options to choose from to find the perfect pair.

But you don’t need to get overwhelmed. In this guide, you’ll discover the most important things to consider before you yes to a certain dress shoe. As you find the right pair for you, you’ll also learn that you can certainly stick to just a few styles that’ll fit your personality despite the vast options.

In addition to knowing the most comfortable dress shoes, which you can discover here, here are ways for you to pick the right pair of dress shoes:

How To Pick A Pair Of Dress Shoes

Start With The Shape

Believe it or not, choosing the wrong shape for your dress shoes can break your carefully curated formal wear. The shape of a shoe accentuates the overall silhouette of your look. That’s why it’s important to choose a trendy shoe but not way too out there.

Gone are the days when square-shaped, skinny-looking shoes were dominating men’s formal wear. So, if you’re still relying on your square-toed dress shoes, it’s about time to toss them out. Today, the trend has reverted to the classic slim and round-toed formal shoes. Rounded shoes are more stylish and elegant compared to the outdated square-toe lace-ups.

While newer styles, cuts, and designs have come up on the market, there is no denying the fact that when it comes to dressing shoes, traditional is the way to go. Brands like pedro shoes are keeping alive the spirit of classic dress shoes and styles. They have retained design patterns that stretch back many decades. Being contemporary does not mean losing touch of the impact traditions have had on the classic dress shoe.

Choose A Style That Speaks You

Of course, the silhouette or style of the shoe matter. As mentioned earlier, there are several styles to choose from, and all of which are worthy of your attention.

However, take note that a good pair of dress shoes do not come cheap. So, if you’ve only got enough money for one pair, you need to choose wisely.

Here’s a list of dress shoes you can look for the next time you visit a fancy shoe store:

  • The Oxford: This is by far the most basic yet most versatile piece of footwear you can own. Oxfords can be dressed up or down whatever the occasion requires. Oxford dress shoes come with closed lacing, which means that the shoes’ faces are sown beneath its vamp, giving it a slim look on the feet.
  • Loafers: These are a type of slip-on shoes made from leather or suede materials. Most people consider loafers to be casual footwear because of their slip-on style of wear. But with the suitable material and fitting suit, you can pull off a pair of loafers even on the most formal occasions.
  • Dress Boots: These are Oxford dress shoes but with a higher cut. When choosing a pair of dress boots, pay attention to the shape and chunkiness of the boots. Dress boots should be sleek to still give off a formal vibe.

There’s a lot more styles than Oxford dress shoes, loafers, and dress boots. But these are the most common silhouettes you’ll find and are the most versatile out of the bunch.

Black Never Goes Out Of Style

A pair of black dress shoes should be a wardrobe essential for every gentleman. Hence, if you only had to buy one pair of dress shoes, it should automatically be a pair of black lace-ups.

Black lace-ups never go out of style. It’s so versatile that you can dress it up or down. Also, it matches your jeans and your suits, except for brown ones.

Additionally, it’s a shoe that chooses no occasion–you can wear it in the office and head straight to the club afterward.

Find The Right Comfort

Of course, you should never put function over fashion. When shopping for dress shoes, buy a pair that fits when you first try it on. Leather doesn’t stretch even after a few wears. For this reason, dress shoes have little to no break-in period.

Remember, you’ll be wearing these shoes probably for hours on end. So, it’s best to buy one that fits (but is not too snug) and provides comfort for all-day use.


Dress shoes are an investment. Since shoes that are able to last for years don’t come cheap, you must know what to look for when finding the perfect pair. Follow these steps to see which type of dress shoes fits your wardrobe-essentials.

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