The Ultimate Guide to Men’s Shoes (And the Suit Color Rules to Abide By)

Guide to Men’s Shoe Styles

The Oxford

 

$190 at Bloomingdale's

If you only get one pair of dress shoes, it has to be the oxford. The essential element of an oxford is that they have laces that use a closed-lace system. Let’s break that down. Dress shoes contain a vamp, which is the front part of the shoe that extends past the eyelids and tongue. In an oxford shoe, the shoelace eyelids are sewn underneath the vamp, which gives the appearance of singular piece of leather (or whatever material the shoe is), instead of a separate area for shoelaces. Beyond that detail, oxfords can come in a variety of styles (like brogue, almond toe, and captoe), but are still a member of the same category. In any case, oxfords are considered to be the most formal dress shoe, which makes them incredibly versatile. These are the shoes that should be worn to job interviews that require a suit and any formal events. Luckily, there is such a variety of options that you’d have to try to be bored by the style. Time to look sharp!

The Derby

 

$200 at Nordstrom

We can’t force you to fill your closet with shoes, but if you already have a pair of oxfords, please get a pair of derbys. They are less formal than oxfords, but still dressy enough for most occasions like a regular day of work or a destination wedding. Unlike oxfords, derbys have an open-lace system, which basically means the part that the shoelaces are attached to are separate piece of fabric (sewn on top of the vamp), which gives a less dressy look. Just like the oxfords, derbys are available in a variety of styles, like wingtips. For suit pairing, stick to formal pairs of the shoe in brown or black. It’s easy to find casual derbys in brighter colors, which tend to be better suited for jeans or chinos, or a fancy beach event.

The Monk Strap

$710 at Todd Snyder

Reserved for only the most stylish men, the monk strap shoe’s iconic silhouette blends formality with high fashion. The shoe replaces laces with either one, two (called “double monk”) or even three, buckled straps. Although one buckle is considered more formal, the double monk style is significantly more popular. It’s less dressed up than an oxford, but a step up from the derby. Think of monk straps as a statement piece; it’s a perfect pair to wear to a movie premier or on a special date with your significant other, but not to a job interview or formal business meeting. Either way, don’t fear the business suit and monk strap combo. It will turn heads for the right reasons.

The Loafer

 

$195 at Nordstrom

Loafers aren’t just for fraternity brothers. These slip-ons come in a variety of styles that range from casual to suit-appropriate. Don’t even think about pairing penny loafers with a suit unless you think you can start a new fashion trend; pair them only with shorts, jeans, and chinos. A good pair of dress loafers tends to have a bit, which is typically a metal piece around the vamp. This style was actually invented by Gucci in the ‘60s, and is now the go-to way to dress up the typically-casual shoe. You can wear loafers in the same way you’d wear a pair of oxfords or derbys for a formal look, which is acceptable in most offices or dressy venues. Alternatively, you can completely transform your suit by going tie-less and cuffing your pants legs to show off your loafers, which will make you look trendy and possibly the coolest dude in the room.

The Chelsea Boot

 

$104.95 at Zappos

Although they feel like a newer trend, the Chelsea boot has been around since at least 1851, with a patent that included a mention of how Queen Victoria is a fan of the style. The Chelsea boot is a lace-less ankle-length boot with a rounded toe that typically has an elastic side that allows you to slip it on with ease. Some manufacturers have mimicked the same silhouette but replaced the side with features like a zipper, but the principles of the boot remain the same. The Chelsea boot is typically casual, but is a step up from a loafer. For a dressier look, stick to all leather without the zipper. If it was good enough for the Queen of England, it’s good enough for us.

The Chukka Boot

 

$375 at Zappos

Chukka boots are a dressed up alternative to desert boots. Chukka boots are ankle-high boots that have two or three sets of eyeholes and a round toe-box. They are open-laced and commonly made with suede, although the dressier variety is made with leather. They can give your suit a casual look that makes it ideal for more laidback or outdoor events. Despite being more casual than most dress shoes, chukka boots still look well put-together and give a sartorial edge that you won’t find on a typical walk down Main Street.

Sneakers

 

$244 at Ace Marks

Pairing sneakers with a suit requires careful planning to avoid coming off as sloppy. If you know what you’re doing, it’s possible to wear just about any (clean) non-athletic sneaker with a suit, but it’s best to start with a pair of all-leather white sneakers. It’s essential to keep everything casual. This is the best time to wear a t-shirt under your blazer. A navy blue suit with a white t-shirt and white sneakers is a classic look for a reason. It works so well because the sneakers provide the perfect amount of contrast. Once you can pull off this outfit (which you can), you can start experimenting with other sneakers, but please save the basketball shoes for the court. And though many have tried, a tuxedo with white sneakers is trying to do too much at once.

The Cowboy Boot

 

$199.95 at Zappos

Unless you’re in West Texas, cowboy boots with a suit is a memorably strong statement, so don’t even think about trying the look out unless you want to be the center of attention, which is not always the goal. Don’t wear your favorite pair of western boots to your next destination wedding unless it’s on a ranch. If you want to attempt the look, you might as well lean into it. If you’re opting for traditional brown boots, they will follow the same rules that any brown dress shoe follows. So one outfit could be a navy suit, cowboy boots, and a bolo tie (remember: lean in). It’s essential that your outfit is well tailored because an ill-fitted suit will give the impression of a halloween costume instead of a cowboy ready for business.

Shoe Toe Styles

Now that you know the main types of men’s shoes, it’s time to talk toes. There are many different styles of shoe toe, which can be found across shoe categories and dramatically change the appearance of your suit. Here are the major toe styles you’re likely to encounter while shopping.

Plain Toe
In a plain toe, there is no stitching or additional detailing on the toe box. Typically, this is considered to be the most formal toe option, although there are exceptions.

Cap Toe
In a cap toe, there is horizontal stitching across the toe box, which breaks up the toe box into two parts. It’s a formal look that is used on many types of dress shoes.

Wingtip
A wingtip is a common style where the detailing on the front of the toe box is spread out to give the appearance of wings, like in a w-shape. Often, this detailing is copied throughout the rest of the shoe.

Split Toe
A split toe is a feature sometimes found on derbys, where there is a vertical line of stitching in the middle of the front of the toe box; as the name announces, it is splitting your toes. It’s not a common feature, but it adds personality to your shoes.

Apron Toe
An apron toe is a design element where there is piece of material that covers the vamp. It’s worth noting that most split toe shoes also have an apron toe. It is also a common feature on penny loafers.

Medallion
A medallion on a shoe is like a minimal version of a wingtip. Instead of dramatic broguing that typically covers the entire shoe, a medallion style is when the front of the toe box contains a set of dots in the front. This is the perfect feature if you want to add a hint of personality to your dress shoe without having the design takeover the entire shoe.

Which Shoe and Suit Color Combinations are Best?

You’ve mastered shoe and toe styles, and now comes the most confusing part: understanding which suit color pairs with which shoe color.

Which color shoes should I pair with a black suit?

Yes, it may seem boring, but stick to black shoes with a black suit. Any other color would bring too much contrast for the classic look that a black suit brings. Still, there are plenty of ways to introduce variety with black shoes. Try out just about any of the shoe types mentioned above, which will give you plenty of room for experimentation. Brown shoes are a definite no.

Which color shoes should I pair with a brown suit?

Believe it or not, the best color shoe for a brown suit is brown. Don’t worry about matching shades. In fact, that’s the opposite of what you want to do. Make sure your brown shoe is a shade darker than your brown suit, this will help draw the eye upwards. Beyond brown, burgundy is also acceptable, but is on the more casual end. Sneakers with a brown suit is a hard look to pull off—if you’re not sure it’s working, it probably isn’t.

Which color shoes should I pair with a burgundy suit?

Burgundy isn’t a typical suit color, so there’s a good chance that you already know exactly what you’re doing if you happen to have a burgundy suit in your closet. Brown is definitely an acceptable choice, but make sure you stick to something like a derby, or even a double monk, instead of a more formal oxford. Don’t attempt to color-match with an oxblood shoe, since it’s unlikely to be the exact shade and won’t provide enough contrast. White sneakers or gray slipper-style loafers would be a fun choice if you want to look laidback.

Which color shoes should I pair with a charcoal suit?

There isn’t much leeway when it comes to charcoal suits. The rule is to avoid brown at all costs. Even though charcoal is considered to be a shade of gray, it will give the appearance of pairing black and brown, which is an obvious no-no. Stick to either black or dark burgundy shoes. From there, the style of shoe that you select will depend on the occasion. As always, oxfords are the most formal, so choose accordingly.

Which color shoes should I pair with a light gray suit?

It’s hard to go wrong with your shoe selection for a gray suit. Light gray is a true neutral, which means you’ll almost certainly be safe. This is your opportunity to experiment with brighter colors if you’d like. The one thing to keep in mind is that if you decide to go with gray shoes, make sure they’re at least a shade darker than your suit. Brown shoes with a light gray suit is the epitome of formal, whereas black shoes tends to be the opposite. You can use this idea to throw on a pair of black Chelsea boots to look exceptionally trendy.

Which color shoes should I pair with a navy-blue suit?

You’d have to try to get a navy-blue suit and shoe pairing wrong. Just about any color is acceptable, but the tried-and-true combination is brown. It’s better to steer towards darker shades of brown, although a light tan is still acceptable. If you have an extensive enough dress shoe collection to own a pair of burgundy dress shoes, now is your chance to really show them off. If your event is on the casual end, don’t fear a pair of leather white sneakers. It’s also common in formal offices to pair black shoes with navy, but make sure the shoes are the traditional variety.

Which color shoes should I pair with a light blue suit?

A light blue suit is nearly as versatile as a navy-blue suit, but brown shoes are still the best color to choose. The main difference is that, unlike with navy suits, it’s better to steer towards lighter shades of brown. Tan shoes will give the perfect amount of contrast and look fresh. As with navy, white sneakers are acceptable, but make sure to wear a t-shirt instead of a tie and button-down shirt to keep the look cohesive.

Which color shoes should I pair with a pastel suit?

A pastel suit is the perfect opportunity to bring some additional color to your feet. At the risk of sounding like a broken record, it’s hard to wrong with a brown shoe or a white sneaker. Like with a light blue suit, it’s better to steer in the direction of tan instead of dark brown, although both color choices will get the job done. Another option here, if it’s not in a clashing shade, is to wear a pair of blue dress shoes. Go with blue suede for major Elvis vibes.

Which color shoes should I pair with a patterned suit?

Patterned suits come in a variety of colors so there is no hard and fast rule when it comes to color. It’s more important to keep the style of the shoe in mind. Since a patterned suit is already pretty busy, make sure your shoes are minimal and informal. There’s no better time to wear luxury sneakers and there’s no worse time for formal oxfords. Follow the above color combination rules to look sharp and fun.

Can I wear sneakers with a suit?

You can definitely wear sneakers with a suit, as long as the event isn’t formal. It’s not a look you’d want to bust out for a job interview or conservative business meeting, but it’s perfectly tailored for a first date, holiday party, or night out for drinks. Make sure you stick to simple, leather sneakers instead of a pair of maximalistic basketball sneakers. It’s hard to go wrong with a pair of all-white leather sneakers. There’s a plethora of designers who make their own take on the shoe, so you’ll find plenty of options to make sure you stick out from the crowd.

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