Wingtips to Loafers: 10 Types of Shoes & What to Wear them With

There will be more times than you realize when it’s required for you to suit up, which we recently covered with our How to Pick The Right Suit For The Right Occasion article.

Even if you purchase the most expensive suit you can find, or at least the most appropriate for the occasion, you can easily ruin it by not having the right type of shoes to accompany it. While you may believe that no one is paying attention to your feet, trust us, someone will. Having the wrong kind of shoes with your attire is embarrassing and classless.

While a quality pair of dress shoes may cost you a couple of hundred bucks, you should keep in mind that they not only complete your suit, they’ll also last for years – since you most likely won’t be wearing them daily.

When looking for dress shoes, remember that leather is the only way to go, and there are numerous colors and styles, so pick a pair that suits you.

To make sure that you have the proper footwear for the right situation, we’re presenting ten types of shoes, and, what to wear them with.


These were originally known as Balmorals in England, but today, oxfords refer to any lace-up shoes that don’t rise above the ankles, and, are great for almost any occasion.

There are numerous varieties to chose from, in color and style, but here’s some basic suggestions.

Black, closed-laced oxfords are best for formal suits and events. They go perfectly with pinstriped suits and double-breasted suits. In fact, any black pair will go with business suits, or with dress shirts and trousers for a less formal look.

Brown oxfords are great with everything from tweed or light suits and sport jackets to jeans and khakis. Oxblood is another color that will work with a lighter colored suit or less formal attire.

When searching for a pair of oxfords, no matter the color or style, genuine leather is essential.


Wingtips are essentially a variation of an oxford. When viewed from above this toe cap style is “W” shaped and looks similar to a bird with extended wings, hence the style name “wingtips”, which is commonly used in the United States.

Wingtips are recommended for less formal events and go nicely with casual trousers, such as corduroys or Dockers.

The Derby (Gibson, Blücher or Bucks)

The Derby and the Oxford are also similar. The main difference is that the Oxford is closed-laced whereas the Derby is open-laced. This type of shoe goes excellent with  khakis and  a blazer during a night out in town.

Cap Toes

Cap toes are essentially decorated oxfords.

In contrast to an oxford, cap-toe shoes have an additional layer or band of leather over the toe, which give them an edge style wise. A stylish pair of cap toes should be reserved for special occasions and be paired only with clothes of equal quality.

Remember, these are the most formal of all dress shoes and are always appropriate to wear with a lounge suit or daytime formal wear.

White Bucks

White Bucks are also like Oxfords – except that they are made of white buckskin. These shoes are flasher and are more commonly worn during the summer months, however, they can also be worn in the spring and early autumn.

You can pair them with a lightweight suit or even jeans, since they’re rather versatile.

Dress Boots

Dress boots are simply slim, ankle-length boots. They are often highly polished and frequently embellished with perforations (known as a wing-tip pattern). These boots will look fantastic with dressy and casual clothes, such as a pair of dark-colored designer jeans, a pair of dress trousers or a casual suit. They’re also perfect for colder times of the year and can provide a more rugged look.

Opera Slippers (Court Shoes)

Opera pumps, which are shiny black slippers with a bow on top, have been worn by kings, statesmen, poets, and other well dressed men for over a hundred years. Needless to say, if you’re attending an event where a tuxedo is required, these are a classical must. While they may have lost favor to lace-up shoes, they’re enjoying a revival.

Loafers (Slip-On)

Loafers are an invention of the 20th Century. They are similar to a moccasin on top, but have a wide and fairly flat heel. Many loafers have tassels, although these are not as common nowadays. Penny loafers have a strap across the upper portion of the shoe, which was obviously originally designed to hold change or an ornament.

Loafers, and slip-on shoes, also come in a variety of colors and styles. They should be worn for more casual and semi-formal events, although they are acceptable for business casual attire as well.

Tassel loafers are more formal and well-suited for business and tailored suits. Suede tassel loafers lean towards a more casual look, and can be worn with linen suits and other informal outfits, like jeans. The classic moccasin-style loafer has been worn by business professionals for sometime, but it also looks great with jeans for a night out clubbing.

Penny loafers are casual, and perfect for khaki-and-blazer outfits. However, penny loafers and suede moccasins are the only “dress” shoes that can successfully be worn with shorts and a polo shirt.

Boat Shoes

The difference between boat shoes and loafers is that boat shoes should be worn with sportier ensembles. This might include clothing such as khaki shorts and golf shirts or polo shirts. Boat shoes are considered to be a three-season item, so they should not be worn during the winter, unless you reside, or vacation, in tropical areas.

Monk Straps

This style of shoe refers to dress shoes that are similar to loafers, in that they don’t have laces. While loafers are typically plain or tasseled, monk strap shoes have a metallic buckle and a leather strap on the upper portion of the shoe. This is a feature that also distinguishes them from cap toes, where the leather strap is located above the toe portion of the shoe.

Monk straps are acceptable with dressy jeans, casual dress pants or in the office.

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