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Dressing The Man

The Complete Rookie’s Guide on the Very Basics of Navigating the Business World in Style

By Spencer Lee Boya

Navigating the business world in style is no easy job. It requires years of education in subjects such as fashion history/color theory etc. This article will serve as a rookie’s guide to mastering the basics of dressing.

Fashion Illustration Archives | Gentleman’s Gazette

A Very Brief History of Menswear

Men did not always dress like those in the image above. In the Georgian period during the 1700s, men were once required to wear feathers, pantyhose, and high-heels. The idea of a group of men in high heels and pantyhose storming around the New York Stock Exchange with its floor covered in feathers that had fallen off their heads may not be the most practical nor aesthetically pleasing to those alive today.

The origin of the ‘Classic Menswear’ that we speak of today strictly began at around the 1900s, widely known as the ‘Height of Elegance’. This ‘Height of Elegance’ is solely conferred by those who attended Oxford University with countless items popularised by its students, such as the Oxford Dress Shoes, Colorful Socks, and Club Ties. As the Americans became more affluent and thus actively broadened their horizons culturally and aesthetically, more started traveling to England and France, bringing back suitcases of the latest fashion.

At the time, the Prince of Wales, later the Duke of Windsor was one of the most influential figures in the history of Menswear. He was known for his impeccable taste and attention to detail which critically shaped menswear both philosophically and aesthetically.

Edward, Prince of Wales, 1926

Formal Day wear for men in the 1740s

Therefore, the art of dressing is all about the philosophical concept of ‘Aesthetics’, defined by Professor Andrew Klevans from Oxford University as ‘clusters of interrelated meanings’. It’s all about the art of combining multi-faceted elements such as Color, Pattern, Silhouette, Shapes, Structure, you name it. It’s all about the attention to detail, and a small change in your ensemble (the technical jargon for ‘outfit’) will truly go a long way.

In the following sections, we will explore the very basics of menswear through critical pieces of garments that you should have in your ensemble.

Spot The Mistakes

This is Erling Haaland, one of the most prolific footballers in 2023. If you can spot 15 rookie mistakes from his dinner suit, congratulations, you know the very basics of menswear and you may start thinking about ‘style’. If you are not able to, please keep reading.

The Suit

The suit is possibly the most well-known and necessary piece of garment in one’s wardrobe. Unfortunately, it comes in countless shapes and forms, styles and colors and hardly anyone can get it right, like Erling Haaland. Broadly speaking, the British, American, and Italian suits are the most mainstream among all. They are loosely categorized by the drape and silhouette, colors, materials, patterns, and lapels.

Loosely speaking, the British suit is usually more structured, with padded shoulders, and comes in mute colors such as navy and charcoal. On the other hand, the American suit is usually relaxed and denotes a ‘boxy’ silhouette. The Italian suit is the most flamboyant of all, and it is not uncommon to find them in hues of Pink and extra wide lapels.

The Lapel

A lapel is a folded flap of cloth on the front of a jacket or coat below the collar. It usually comes in three styles, the Notch Lapel, the Peak Lapel, and the Shawl Lapel. The Notch lapel is only appropriate for business casual wear, while the Peak lapel is appropriate for both casual and formal wear. Finally, the Shawl Lapel is reserved strictly for smoking jackets and dinner suits (tuxedo in American English).

There are multiple minor differences in a tailored suit in every town in Italy, therefore this only serves as a broad representation.

The material of the lapel must be taken into strict consideration when purchasing formal wear. Although the peak lapel is appropriate for both casual and formal wear, a dinner jacket is different from a normal suit jacket. The dinner jacket has a satin lapel, with a satin button, while a normal suit will have a lapel of matching fabric with the rest of the suit.

Dinner Suit VS Normal Suit

Pick Stitching on a Lapel

A pick stitch in sewing is a simple running stitch that catches only a few threads of the fabric, showing very little of the thread on the right side of the garment. It is also sometimes known as "stab stitch”. Gentleman, you want to see pick stitches on your suit lapel. It is not just the symbol of quality, but a serious indicator between insiders and an outsider. By the way, if you don’t see pick sticking on your suit lapel, more likely than not, the lapel is stuck together by glue and will fall apart after a few washes. Also, if you see pick stitching on a $150 jacket, more often than not it is there to fool you. See the illustration below.

Look closely along the edge of Beckham’s lapel

A Note on Buttons

It is critical to note that if you have a suit jacket with 2 buttons, always leave the second one undone, it is there for decoration only. When there are three buttons, always keep the second button buttoned, and you may choose to button the first as well.

The Cap Toe Oxfords

If you want to know someone is well dressed, look down. Dress shoes are just as important to your ensemble as your suit, but again, they can easily be overlooked.

The choice of dress shoes should be informed first and foremost by formality. For instance, a pair of opera pumps are not appropriate for a meeting over coffee and a pair of espadrilles are not appropriate for a black tie dress code.

The most common and the safest choice for the average person would be a pair of cap-toe Oxfords, popularised by students at Oxford University in the 1920s. Owning a pair of quality Oxford shoes will simply allow you so much versatility to style it with everything from a seersucker suit for the beach to fully satisfying a black tie dress code.

A pair of cap-toed Oxfords from the English Shoemaker Crockett and Jones

Ties and Pocket Squares

If Eau De Parfumes is the cheapest way for luxury brand fanatics to buy into the world of Gucci or Christian Dior, Ties, Pocket Squares, and Socks are the simple most cost-effective way to elevate your look.

We have all been taught the four-in-hand knot in our youth, unfortunately like everything else above, few can do it right.

Two of the most important things to keep in mind are the dimple in your tie knot and to ensure that it is attached properly to your shirt collar, to avoid looking sloppy. Looking at the image on the left, the dimple in the knot provides a strong structural support to the overall silhouette of the tie knot and gives it a three-dimensional look. Whereas if we look at the image on the right, we can barely tell the difference between the knot and the blade of the tie. Even worse, the tie is detached from the shirt collar, which denotes a lack of attention to detail and just a general sense of sloppiness.

The pocket square is your best opportunity to bring in character and style. There are countless ways to fold a pocket square for different occasions and styles. No matter your choice, a pocket square is necessary to elevate your ensemble.

As a rule of thumb, you do not want your pocket square to share the same pattern as your neckwear, as you are giving away the best opportunity to add dimension and depth to your ensemble. You always want your pocket square to share some color with the rest of your ensemble to look coherent, which is the key to being sophisticated and convincing.

Where To Shop?

We have covered the bare minimum basics to putting together a coherent ensemble, but where to shop? Here are some recommendations for different price ranges. This list only comprises the rack suits as tailored garments are a different ball game.

Above the $2000 range 

  1. Brunello Cucineli, the epitome of the off the rack tailoring, shop here for a  clean and classic look.

  2. Ring Jacket, the Japanese’s take on classic Western tailoring, known for its  attention to detail and craftsmanship.

  3. Ralph Lauren PURPLE Label, the top tier label from Ralph Lauren, can be  easily styled with products from cheaper lines, great versatility, and a one-stop shop.

Circa $1000 range 

  1. Brooks Brothers, the founding father of off the Rack tailoring, great for  business wear, arguably best value for money even comparing to those  above the $2000 range.

  2. Pal Zileri, another Italian brand, offers a contemporary take on tailoring,  incorporating many avant garde elements but remain classy.

  3. Hackett, due to the pressure of the pandemic, the Savile Row tailor started  offering a wider range of off the quintessentially British rack products.

From $300 to $800

  1. Suitsupply, the absolute go to for those on a tighter budget but want to  invest in a good suit.

  2. Hawes and Curtis, another one stop shop for all thing basics and offers  great deals for shirts, accessories and dress shoes 

  3. Spier and Mackay, directly states that they offer the best valued suits, and quite rightfully so. You can land some quality garments at $300

Closing Remarks

The art of fashion is an erudite area of study just like Astrophysics or Classical Music. When making a fashion choice, like making an argument, it's all about being coherent to be convincing. If you want to convey respect for your guests when welcoming them to dinner and decide to show up in a dinner suit like Erling Haaland’s, a disparity can be apparent between your intentions and actions. 

The above guide only covers the most critical pieces in the Western world of Menswear and hopefully, it managed to throw you down the rabbit hole to explore further.


Spencer Lee Boya

Spencer Lee Boya is a Multi-Disciplinary Artist and Entrepreneur reading Entrepreneurial Studies as the ESG Scholar at King’s College, Cambridge. He is currently devoting his time to his newly established social enterprise: The Social Canvas Projects. The organisation aims to reimagine the power of the creative arts in driving social change—and to inspire more creative artists to dedicate their artistic practices to creating social impact in this evermore-divided world.

As a Multi-Disciplinary Artist, he is a classically trained conductor, composer, and pianist who has composed extensively for film, concert, and theatre music. Spencer’s works for film and TV have been screened at Academy and BAFTA awards-qualifying Film Festivals in Tokyo (Animation Short: K.I.T), Belgium, Dublin (Visual Poem: The Snowglobe), Berlin (Animation Short: Sweet Dreams), Los Angeles (Short Film: Morendo), and more. His recent concert piece ‘An Ephemeral Bagatelle’ for string orchestra was played at the Royal Academy of Music—and his Original Music ‘Gabrielle’ played 3 sold-out concerts in Greenwood and George Wood Theatre in London, and was named ‘an iconic performance’ by the China Daily and Shenzhen Daily.

Important Disclaimer: The contents of this article are written according to expert art/fashion historian-conferred ideas (as well as expert-conferred aesthetical judgments). It does not aim to promote or denounce any ideologies beyond the art of dressing. Most importantly, it speaks strictly of Western fashion in the English-speaking world only.

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