The Best Men’s Dress Shoes for Any Business Casual or Formal Fit

Contents

Oxfords
Derbies
Loafers
Monk Straps
Chukka Boots

Are you looking forward to a specific special occasion in order to show off your style? If you are, be sure to grab this opportunity to elevate your style game with a pair of men’s shoes, specifically dress shoes. Of course, it all comes down to understanding the basics.

There are various types of dress shoes, ranging from Derbies to Chukka boots. And, understandably, it can be confusing to learn about what makes each style tick. That’s why we created a comprehensive guide to men’s dress shoes, containing brief information about each type and a few roundups from some of our favorite men’s online clothing stores.

Oxfords

These are the most common, classic, and timeless styles of dress shoes. If you’re looking for something like a one-and-done pair to pair with all your formal attire, then this style might be it. While Oxfords and Derbies can look similar, they differ by their shoelace tabs. Oxfords feature a closed lacing system that only opens at the top. The line down the middle of the laces will be a “V” shape, as opposed to two parallel lines. This makes the silhouette of the shoe slimmer, more streamlined, and therefore more formal.

To confuse you even more, Oxfords can be considered a brogue or cap toe (more on that later). All you need to focus on here is the lacing system. Check out exactly what we mean in the styles ahead.

Cole Haan American Classic Gramercy Cap Toe Oxford

See how the lacing system here remains closed? That little detail helps streamline the entire shoe, determining its style. You’ll see that it appears sleek and sophisticated. These from Cole Haan are a great choice for the everyday suit wearer. It’s a mid-level price point and a shoe you can depend on. The cap-toe detail on these Oxfords is a fun touch.

Salvatore Ferragamo Cap Toe Oxford Shoe

It gets confusing when you throw the term Brogue into the mix. But fear not! All you have to remember is that Brogues denote broguing. This refers to the perforated dots on the shoe. Brogues can come in any style of shoe (even sneakers) but we like them best in an Oxford, especially when they are Ferragamo.

Paul Smith Brent Leather Oxford Shoes

These lovely Oxfords insinuate luxury and elegance at a non-luxury price. They also boast tonal rubber soles for maximum traction, as well as leather footbeds that are embossed in foil for long-lasting comfort. This elegant pair is an example of footwear that will last you many years.

Derbies

Derbies are often confused with Oxfords because at a glance they appear almost the same. But if you look a little closer, you will see that Derbies have an open lacing system. Instead of seeing the “V” shape, you will see two parallel lines or an open wing shape. Derbies are actually preferred for guys with bigger feet because the open system allows for more room and comfort. With that said, they are considered slightly less formal than the Oxfords above. Check out some of our favorite Derby options ahead.

Cardineli Cap Toe Derby

Just like an Oxford, Derbies can come in the form of a cap toe, too. It actually makes the relaxed silhouette feel fancier than usual. Plus, this classy pair sports a cushioned footbed for maximum comfort, perfect for all-day use and long business meetings.

Thomas & Vine Legion Woven Plain Toe Derby

The basketweave design adds interest to an otherwise basic shoe. A lovely all-season footwear especially during the spring and summer, the Thomas & Derby Legion Derby comes with a second set of colored shoelaces for added sophistication. Given its wallet-friendly price, you’ll never think twice about investing in this stylish pair of Derbies.

Gordon Rush Fletcher Buck Shoes

These Derbies from Gordon Fletcher are for the fashion risk-taker. The chunkier fit and sole make the vibe skew chill but elevated. The Italian leather oozes the feeling of luxury. You get what you pay for in terms of comfort, so know that when you go into making this very worthy investment.

Loafers

Loafers are probably the most versatile shoe on this list. That’s because they can be worn with any outfit, formal or casual, and during any season. Even if you’re wearing track pants, your loafers show just how sophisticated you are (see Scott Disick style).

M. Gemi The Filare

Take a shot every time you see us swoon over Italian leather. Just kidding. But M.Gemi is truly one to lust over. The brand is known for its handmade Italian shoes and beautiful materials. This modern take on the classic Penny Loafer can be worn in many different ways and is worth the investment.

Paul Stuart Hope Tassel Slip-On Loafers

This is where dress shoes can become fun and fancy. Crafted from velvet, Paul Stuart’s Hope Tassel Loafers feature a slip-on style to ensure a snug, comfy fit. If you’ve got the confidence to rock these Italian-crafted blue velvet tassel loafers from Paul Stuart, we fully support you. Live your best life.

G.H. Bass & Co. “Larson” Weejun

These are the most classic idea of a loafer, highly revered by icons like JFK and James Dean. This slip-on style mimics the feeling of slippers but can pass as a suit-appropriate shoe. Every guy should own a pair of Weejuns.

Boss Portland Bit Loafer

The rich texture in these Boss loafers makes them one of those pairs that get better with age. You can wear the Boss Portland Bit Loafer during your commute since the pair is constructed from water-resistant, full-grain leather, protecting your feet from the rain. Overall, it’s a classic, timeless style that will polish any outfit.

Monk Straps

You have probably seen these before in your favorite department store but never knew the name or thought that you could even possibly pull them off. Well, I’m here to tell you that you totally can. Here’s the deal. Monk Strap dress shoes have become popular over the last decade. While they aren’t at their peak per se, they are definitely still relevant to those that are up for more of a fashion kick. They offer a cool, sophisticated edge and tell the world you are here to express yourself.

Wolf & Shepherd Gambit Double Monk

One more time for the premium Italian leather! These babies from Wolf & Shepard are an ideal double Monk. Designed to provide you with all-day comfort, Wolf & Shepherd’s Gambit Double Monk Shoes look best with navy trousers, hemmed to show just the tip of your dress socks.

Reiss High Shine Leather Monk Strap Shoes

Woah. Double Monk Strap and High Shine?! These are your subtle statement shoes. With the pair’s premium high-shine leather finish and signature double buckle fastening, you’ll surely be a subject of conversation at a lavish party or meeting. In fact, they will make you look like a million bucks for under $500.

Steve Madden Beaumont Black Leather Shoes

Shoutout to Steve Madden for creating the most accessible yet stylish shoe. If you’re willing to give the Monk Strap a try, maybe start with a good style that won’t entirely break your bank, such as the brand’s Beaumont Black Leather Shoes. Pair it up with a suit for a sophisticated look.

Chukka Boots

Before we get into it, let us warn you that not all Chukkas are meant to be dress shoes. You might be shopping on your own and stumble upon a style name that says “Chukka.” If it appears to be casual, follow your gut and stay away from pairing that with your made-to-measure suit. It’s usually the wider, chunkier Chukkas that are meant for more casual outings.

With that said, when you do shop for dress-shoe Chukkas, you’ll appear to be a very advanced style maven. They are easy wear, but not a basic combo. Chukka boots can be considered fancy because they have a streamlined appearance, similar to the Oxford but with a high ankle. Think of it as your happy medium between shoes and boots.

Thursday Boot Co. Scout Boots

Thursday Boot Co. has made some of the most durable footwear in the game, and their more formal options are just as notable. Blending British and American styles, Thursday Boot Co.’s Scout Boots boast versatility to complement your outfit, allowing you to make a powerful fashion statement anytime, anywhere. Other than their water-resistant stitch-out construction, the pair comes with studded rubber outsoles for better grip to reduce the likelihood of slips and falls. If you need an aesthetic pair that will help you power through your day, we recommend giving these Chukka boots a try.

Ted Baker London Crint Leather Desert Boots

Desert Boot vibes but with a formal feel. These Chukkas from Ted Baker are the classiest you can get. They come in both black and dark tan to cover your entire wardrobe. It’s the best option for your seasonal formal wear.

Brooks Brothers Suede Chukkas

Don’t worry, we didn’t forget about your navy attire! To some guys, this space feels like home. These suede Chukkas from Brooks Brothers are a product of meticulous Italian craftsmanship, designed to provide long-lasting comfort to their wearer.