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It's not just important to have a good pair of dress shoes; you need a great pair. Sneakers are great and all, but there are some situations where they simply won't cut it. Some events call for shoes that are both elegant and timelessly classic, such as weddings, funerals, job interviews, and meetings with corporate executives. It's been a while, but now is the time to break out your best pair of dress shoes.

There really are choices for every taste. If you have the financial flexibility to do so, don't be afraid to pay a little more for the experience. That doesn't mean you have to go into debt, but remember that investing in a pair of shoes that will last rather than one that will just last a few months is worth the extra money.

Also, the most reliable method of making sure your cash is well spent is to Aware of the landscape Therefore, you can find an item that complements your current wardrobe without breaking the bank. Every man should be familiar with these eight classic dress shoe styles: the oxford, derby, brogue, loafer, chukka, Chelsea boot, monk strap, and Venetian slipper.

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Among the many options for formal footwear, an oxford is a good choice for those with limited storage space. It's the kind of look that pairs well with a tuxedo or a dressy business suit, so you'll never be unprepared for a formal business event. This is because of the "closed-throat" construction of the oxford, in which the leather around the laces (the quarters) meet at the base and are sewn into the vamp (the leather that runs down your instep and towards the toe).

In all candor, though, you need not devote an inordinate amount of time to the jargon. Check the area above the shoelaces. Does it look like the letter "V" instead of a collection of parallel lines You have an oxford, and its trim cut ensures that you will look presentable at any formal event.

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Even though derbies aren't quite as formal as oxfords, don't let that stop you from wearing them. A quality pair will complement any suit (except perhaps a tuxedo if you're going to be in the company of strict black-tie purists). As an added bonus, the open-throat design is versatile enough to be worn with anything from jeans to tweed slacks because the leather around the laces runs parallel to, and over the vamp. Derby shoes are a safe bet if you're the type of guy who wears suits on the regular but also needs a pair of shoes on hand for date night on the weekend.

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Brogues are not so much a shoe shape as they are the ornamentation on top of a shoe shape. Shoes with these distinctive perforations were originally created for a practical purpose: to allow water to escape while stomping through Irish bogs. These days, it's purely decorative, but it's still a staple of most modern men's dress shoes.

Brogues are sometimes referred to as wingtips, and that's not without merit. From the tip of the toe, you'll find decorative "wings" on two of the most common styles. They're the kind with long wings that go all the way around the shoe. The midfoot is reached before the shortwings begin to wrap. Cap-toes and other decorative features can also feature brogueing. A pair of derbies, oxfords, monkstraps, or ankle boots could feature such details. When it comes to brogues, fashion is subjective.

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Some people, for a while, considered loafers inappropriate for business attire. Find out from your father or grandfather. For the most part, those times have passed. To complement even the slickest two-button slacks, slip-on styles are now available in a variety of sleek and sophisticated silhouettes. The most common variations are penny loafers and bit loafers. Loafer legend has it that the cutout in the strap across the shoe on pennies was meant to hold a penny. Bit loafers are distinguished by a decorative metal strap across the foot.

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The chukka is an unusual shoe. Some of them look like they belong on a building site rather than in an office setting. But there are others They are just as sophisticated as the other examples here. To pull this off, you need to give priority to a sleek silhouette and premium construction. In most cases, this means that the boots are shorter than usual, with a more pointed toe and sleek lines leading up to the ankle, so that they can be worn subtly under dress pants. Try to find something with that, and ideally something with a sole that isn't too thick.

Commonly known as "Chelsea Boots,"

The Chelsea boot has been worn by the most influential people in British fashion history, from Queen Victoria to the Mods to Daniel Craig. The style of shoe was originally worn by wealthy white Anglo-Saxon Protestants (WASPs) and was named after a posh section of London. Ankle boots are versatile footwear that can be worn year-round, regardless of the season. When paired with a slim suit, the Chelsea boot is a knockout. The Beatles in the '60s come to mind. Is there really a need to elaborate?

Belts with a Monkish Flavor

If you need security but hate laces The monk strap is where it's at. The shoe is easily recognizable by the one or two (or more, in rare cases) straps that cross over the vamp and buckle at the toes. According to legend, it was first worn by monks in Europe in the 15th century, hence the name. Later on, in the 1920s specifically, the monk strap became the preferred shoe of gentlemen who, for various historical reasons, favored a more subdued and refined look. While that remains true, in more recent decades we've seen a number of labels put a fresh spin on the look by using exotic materials like leather and bright colors.

Slippers from Venice

In contrast to the penny and the horesbit (discussed previously), the Venetian loafer does not lend itself well to a relaxed style of dress. Perhaps leisurely, but definitely not informal The most elegant footwear available, this design is perfect for a night out on the town with a Cuban cigar and a bottle of sherry. For this reason, some iterations of the Venetian loafer are known as smoking or dinner slippers. The upper of these shoes, which is typically leather or velvet, is bare of any decorative elements, representing luxury in its purest form.

Miako Katoh was responsible for the prop styling.

Photographs by Allie Holloway

Headshot of Jonathan Evans

Mr. Jonathan Evans

Jonathan Evans, Esquire's director of style, writes about men's style, including clothing, grooming, and accessories like watches and shoes. There, he and his family make their home in Brooklyn. If you're on Twitter or Instagram, you can find him as @MrJonathanEvans.

Headshot of Barry Samaha

Samaha, Barry

Former fashion and grooming expert Barry Samaha was Esquire's style commerce editor. He has worked as an editor for Harper's Bazaar, Surface, and WWD, and he is currently in charge of the editorial content at Tod's Group. Among the many publications he has contributed to are The Daily Beast, Coveteur, Departures, Paper, Bustle Group, and Forbes. He calls New York City home and has trouble fitting all of his footwear into his closet.  

Rabbi Avidan Grossman

At Esquire, Avidan Grossman handles all things related to men's style on the internet, including the publication's coverage of clothing, footwear, grooming, and accessories. As a result, he takes excessively long to get dressed. Obviously, his parents still have no clue as to what he does for a living.