Not only is it wise to invest in a good pair of dress shoes, but it’s also essential. Even the nicest sneakers sometimes won’t cut it. Sure, sneakers have their purpose. There are some events that call for footwear that is both elegant and classic, whether it be a wedding or burial, a job interview, or a meeting with the top executives from corporate. The time has come to once again don the cutest pair of dress shoes in your collection, even though it has undoubtedly been a while.

Style and fit are the two most important considerations when choosing a dress shoe. Finding the ideal pair of dress shoes involves picking one that complements both your style and your feet. We looked for the best dress shoes to aid you in your search for the ideal pair, from the timeless to the eye-catching.

Oxfords

Consider an oxford first if you’re only going to have one pair of dress shoes in your closet. You won’t ever be without options for a major work event—or if you need to put on a tux. It is the style that can go with your most formal options. This is made possible by the “closed-throat” structure of the oxford shoe, in which the leather that surrounds the laces (the quarters) converges at the base and is stitched to the leather that extends from your instep to your toe.

However, you don’t need to spend a lot of effort on the terms. Simply glance at the eyelets and top of the shoe. Rather than a series of parallel lines, does it create a “V”? The sleek silhouette of your oxford ensures that you will seem put-together for any dressy occasion.

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Brogues

The detailing that goes on top of the silhouette, not the silhouette itself, is what we’re referring to when we talk about brogues. Traditionally, the distinctive perforations served a practical purpose, allowing water to drain from shoes worn when walking through Irish bogs. Currently, it serves as ornamentation, but formal shoes still rely on it heavily.

There’s a solid reason why brogues are often known as wingtips. Two of the common shoe types contain ornamental “wings” that extend from the shoe’s toe. They wrap around the back of the shoe with longwings. They wrap around mid-foot with shortwings. Of course, cap-toes and other design components also feature brogueing. A pair of derbies, oxfords, monk straps, or even ankle boots might have those components. Everything about brogues is a question of personal preference.

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Loafers

Some people once believed loafers were too casual to be worn with a suit. Just ask your fatherMagnanni Raso Loafer or even your grandfather. Thankfully, those times are a distant memory. The slip-on design is now available in styles that are fashionable and elegant enough to pair with even your sharpest two-button. The two variations that you’ll most frequently see are penny loafers and bit loafers. According to loafer lore, there is a strap across the shoe with a cutout on coins that was intended to hold a penny (it probably wasn’t, but it’s still a funny story). Bit loafers include a decorative metal component across the foot that nonetheless has a stylish appearance.

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Chelsea Boots

The largest British trend-setters, including Queen Victoria, Mods, and Daniel Craig, have all donned Chelsea boots. Even though it was named after a wealthy area of London and popularized by WASPs, the style has now evolved into one of the most democratic and universal footwear options available. It is an ankle-height boot that can be worn in the summer or the winter, while working or not. It is typically made of leather or suede. Particularly when worn with tapered-leg suits, the Chelsea boot looks fantastic. In the 1960s, consider the Beatles. Need we say more?

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Derbies

Don’t let the fact that derbies are technically a touch less formal than oxfords scare you too much. If you’re going to be surrounded by black-tie traditionalists, a good pair may not be appropriate with a tux. Additionally, the open-throat silhouette—where the leather around the laces continues parallel and over the vamp—works well with both jeans and tweed pants. Derbys are a good choice if you’re the kind of guy who occasionally wears a suit but also wants a pair of shoes on hand for a date night at the weekend.

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Monk Straps

Although you dislike laces, security is still a must. The monk strap is the only thing you need. The straps, which fold over the vamp and are secured at the ends by buckles, give the shoe its distinctive appearance. They can be single or double (there are a few exceptions when there are more). According to legend, it was first worn mostly by monks in Europe in the fifteenth century, therefore its name.

Later, especially in the 1920s, the monk strap emerged as the chosen shoe for gentlemen who, because of history, wanted something dignified and reserved. Although that notion is still valid today, numerous companies have started to recreate the look in recent years by using exotic leather and vibrant colors in their creations.

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Venetian Loafers

The Venetian loafer can’t really be casual, unlike the penny. Possibly leisurely, but not casual. It is the most opulent shoe available; the kind that would be worn to dinner with place cards and an excessive amount of cutlery or while smoking a Cuban with a glass of sherry. For this very reason, some variations of the Venetian loafer are referred to as smoking or supper slippers. It is a shoe that exemplifies luxury at its purest and most straightforward. The upper, which is typically made of leather or velvet, is distinguished by its absence of any ornamentation.

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Patent

Patent leather shoes are considered the pinnacle of special occasions by fashion purists, calling for a full tuxedo suit and matching tuxedo shoes. However, aren’t laws designed to be broken? In light of this, it’s not unusual to see them worn these days with jeans or even white athletic socks and shorts. Although the majority of today’s supply has a synthetic coating, the “patent” look was traditionally produced using a linseed oil lacquer finish. Any crease or scratch looks unsightly because of the shoe’s extremely polished exterior in either circumstance. That would be the one reason to wear patent leather shoes in moderation.

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