5 Options For Your First Pair of Dress Shoes

Every man should have a decent pair of dress shoes in their wardrobe. Buying your first pair of dress shoes is just as big and important a milestone as buying your first suit.

In fact, we think it’s even more important. After all, you don’t just wear a dress shoe to the office. You’ll also wear them on dates, on big nights out to bars and clubs with your friends, and just about any other special occasion you can think of.

The dress shoes will make or break your outfit. Let’s face it, that’s a lot of pressure on a pair of shoes!

But with so many different kinds of quality leather shoes on the market, it can feel impossible to know where to start. Don’t worry: We’re here to help! Now is the perfect time to upgrade your shoe collection, and here are our picks of the very best shoes you can choose:

Choose a Chelsea Boot

Chelsea boots might not be the first and most obvious choice when you start thinking about dress shoes, but they are an ideal pick if you’re looking for something versatile that you can wear for both formal and informal occasions.

A leather Chelsea boot will offer simple and clean lines that will look great worn with both dress pants and jeans.

5 Options For Your First Pair of Dress Shoes : Footwear | https://www.royalfashionist.com

Harry Styles isn’t famed for his commitment to formalwear, but he is known for his passion for fashion. He injects grown-up style and formality into this casual outfit by pairing his skinny black jeans with coordinating black Chelsea boots. These same boots would look just as good paired with a dark suit and slim fitting shirt. 

Black Chelsea boots are the best choice if you want something that is as formal and easy to wear as possible; this is because black is a wonderful colour you can wear with almost everything. It doesn’t matter whether you’re looking for boots to wear with blue jeans, black jeans, a black suit or a charcoal one, black Chelsea boots will coordinate perfectly.

Chelsea boots are a  pick for dress shoes during the winter months, offering extra warmth and support, but they shouldn’t be dismissed during the summer months. They can add an edgy, rock and roll-inspired feel to your formal outfits.

5 Options For Your First Pair of Dress Shoes : Footwear | https://www.royalfashionist.comWhen it comes to choosing the right Chelsea boots for you, we love the leather Wyatt Chelsea boots from our own Royal Fashionista collection.

They slip on and have a convenient zip fastening, making them easy to wear. Made from genuine cow leather which has a gentle sheen, these boots also have a pointed toe to add extra style credentials.

Because they can also be worn for a myriad of casual occasions, Chelsea boots are a great introduction into the world of wearing dress shoes for guys that are either younger or prefer a more casual aesthetic.

Bring in a Brogue

Brogues once had a reputation for being too stuffy: they were the staple shoe of old men and bankers, and were at the height of their popularity in the 1970s and 1980s. But in recent years, brogues have seen a massive revival.

They have been reappropriated by the young and the hip, and now they are not only worn as a formal dress shoe but as a fun casual shoe too. The most popular choice when looking for a brogue is to choose a brown version; this will contrast with the colour of your pants, and

5 Options For Your First Pair of Dress Shoes : Footwear | https://www.royalfashionist.com

Is there anyone more fashion-forward than David Beckham? If he’s wearing brogues then it’s a shoe worth wearing! Note that he has chosen a two-tone shoe that coordinates perfectly with the color of his suit.

Not sure what a brogue is? A brogue is a formal leather dress shoe designed with punched leather hole details across the upper.

In the 18th century, these holes were originally designed to drain out any water that may form in the shoe as a result of walking across boggy Scottish marshes. Now they are simply a style feature.

We suggest opting for a medium brown brogue that would look great paired with a grey or blue suit but would look equally as fashion-forward paired with a simple jean or chino.

If you really want your shoes to make a statement (and your feet to do all the talking) then why not opt for a two-tone brogue? Two tones of leather will make your shoes much harder to coordinate with your outfit, but if you can get it right then you will steal the show for all the right reasons.

Stand Out in A Monk Strap

A monk strap or double monk strap shoe is a shoe which is fastened with buckles rather than with laces. It is often known as the most ‘advanced’ dress shoe, and it is certainly the most detailed and unusual shoe on this list.
5 Options For Your First Pair of Dress Shoes : Footwear | https://www.royalfashionist.com

David Gandy, a model best known for his commitment to fine tailoring and looking dapper for every occasion, often favours the monk strap shoe, and it’s easy to see why.
He oozes Italian inspired style here, pairing a double monk strap show with white chinos and a close fitting double breasted jacket. 

Double monk straps look great worn on traditional loafers, and this typically old-fashioned shoe is bang on trend for 2019.

The double monk strap is the more fashion-focused look, but these shoes are also very stiff, making them uncomfortable to wear if you have a high arch, or are looking for a shoe you can wear all day, every day.

By contrast, the single monk strap version is softer and more flexible. It also lends the manufacturer more options to inject some individuality and style into the shoe.

The thickness of the strap, the angle it sits at, the size and shape of the buckle, and the color of the cut out can all be modified until you have the perfect shoe.

These are definitely the shoes to choose if you want to stand out from the crowd for all of the right reasons!

Look Continental In An Oxford

The Oxford is the most popular and traditional of all the dress shoes, and that also makes it one of the easiest to wear. Most men will opt for a simple black leather option when choosing their first pair of dress shoes.

There are many reasons for this; Oxfords are a classic suit shoe that will look great worn with a suit for prom, graduation, and the many other formal occasions you have to attend during your formative years.

5 Options For Your First Pair of Dress Shoes : Footwear | https://www.royalfashionist.com

Taye Diggs wears his oxfords with a pair of formal dark pants. He injects personality into the shoe by adding blue laces, and his statement scarf and hat lend his whole outfit a fashion-forward feel.

They’re also versatile enough that you can wear them for weddings, job interviews, internships and work experience, and other office-based situations. Basically, the Oxford is the workhorse of the dress shoe family.

Now, we’re not going to lie to you and say that this is the most stylish dress shoe you could choose. But what it lacks in style, it makes up for in practicality. And, if you choose the right shoe, Oxfords can still have high- fashion credentials.

Look for an Oxford with a hard leather sole and a slightly pointed toe. The shoe you choose should also have a soft sheen so that it’s easy for you to polish them to perfection.

Unlike other shoes on this list, the Oxford isn’t versatile enough to be paired with jeans, so don’t worry too much about how it will fit into your casual wardrobe. It’s all about looking dapper, and showcasing your formal style.

Wow in Wholecut Shoes

Finally, if you’re committed to minimalism and are looking for a dress shoe that will lend your outfit a streamlined aesthetic then why not invest in the lesser known wholecut dress shoe.

Many men aren’t entirely sure what a wholecut shoe is, but it’s really quite simple: this is a shoe that is cut from just one piece of leather, meaning that there are no panels, no stitching, and no detailing to detract from the quality of the material at all.5 Options For Your First Pair of Dress Shoes : Footwear | https://www.royalfashionist.com

The fact is that wholecut shoes are expensive: these aren’t the kind of shoes to look for if you want to stretch a tight budget. They are pricey because the quality of the leather they are constructed from is so important: the skin is flawless and a great deal of expertise from a high-end craftsman has to go into making these kinds of shoes.

5 Options For Your First Pair of Dress Shoes : Footwear | https://www.royalfashionist.comWearing a wholecut shoe immediately shows that you understand fashion, that you care about quality and artisan craftsmanship, and that you’re prepared to invest in the finer things in life. If you want to impress a woman who knows a thing or two about fashion, these are the shoes to wear!


When it comes to picking a pair of dress shoes, choose wisely. Unless you avoid leather for ethical reasons, we would always recommend choosing a high-quality pair of leather shoes, and spending as much as you can afford.

Leather shoes are well worth the investment: leather only looks better as it ages, and is easy to care for. When you polish a pair of leather shoes, you can quickly make them look as good as new. This means that they’ll last longer, helping to justify the higher initial price point.

Different shoes work well for different occasions, but if you can only afford to invest in one pair of dress shoes, we would recommend opting for either a simple Oxford shoe or a Chelsea boot, depending on the time of year and where you intend to wear them.

Whichever pair you choose, it’s essential to ensure that you have at last one pair of dress shoes in your wardrobe. Once you buy them, you’ll wonder what you ever did without them: you’ll be amazed at how often you wear these formal but versatile essentials.

Tor Brierley is a writer and editor from the UK whose love of writing about fashion has taken her all over the world. With a passion for tailoring, Tor often looks to menswear for inspiration, and believes that fashion should be accessible to everyone. Tor has three main obsessions: red lipstick, her kids, and finding the perfect leather jacket.

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