5 Essentials For Men’s Wear (Part 2): What Every Man Should Know

Recently, we looked at the 5 Essentials for Office Wear for men and how you should go about building your professional wardrobe. We looked at suits, trousers (or dress pants), dress shirts and dress shoes, as well as the guidelines outlined by the “experts” on what is appropriate and professional, yet fashionable and stylish.

Now, lets look at the 5 Essentials for Casual Wear and what the guiding principles are in such a fashion-forward and image-conscious world.


Jeans are a staple in most, if not all, cultures. But with the evolving world of fashion, the styles of jeans out there can be daunting — and I’m speaking as a woman here. In order to find the perfect pair of jeans for your body type, you will have to try on many pairs before you find “the one.”


The most common styles today are the Boot Cut, Relaxed and Straight Leg. These are the easiest to wear, and they fit most body types. The relaxed fit and straight leg offer more room in the legs and are suitable for very casual activities. The boot cut tapers at the knee but falls away so the hem sits nicely on the foot. The fit is still loose in the leg and is considered the most formal of the three in that it can be dressed up with a dress shirt or blazer. These fits are perfect for the average man, whether you have an athletic build or are sturdy.

If you consider yourself more stylish, however, you can look at the Slim Fit or the Tapered Slim Fit shown above. As mentioned in the previous post, the slim fit look is in and will be around for a while. They offer less leg room, as they are designed to make you look slim; “they are crisp, and sharp.” Then there is the Skinny and Super or Ultra Skinny Fit. Some men can get away with wearing skinny jeans, and that is because they are really skinny themselves. But skinny jeans are not made for everyone. Just remember:

“Fit is good. Snug is dicey. Tight is just WRONG.”

— Esquire.com

collage-Skinny vs Slim20120709-012825

When buying jeans, go for the darker denim, as it can be dressed up or down with a white oxford and blazer, or just a simple T-shirt. The lighter blue denim, however, is more casual looking than its darker counterpart. If you choose to get both however, you’ll be fine. Just avoid acid wash, ’90s faded blue or gray, evident whiskers (faded lines running across the groin) and other graphic washing processes. And while we’re on the topic of what to avoid, please also steer clear of studs and rhinestones, as well as gigantic logos or graphics. Leave those for high schoolers and college students.

Jeans are not to be washed as regularly as other clothes, as washing deteriorates the fabric and shortens its life span. But for your first wash:

  • Wash the jeans by itself, as there is sure to be some colour bleeding.
  • Line-dry your jeans inside out to preserve the colour.
  • And if you’ve bought a pair of jeans but find it needs to be tailored, wash the jeans beforehand, as washing tends to shrink the jeans a bit. You do not want your tailor adjusting your jeans at its maximum capacity, thereby making them tighter or shorter than needed.

Other Pants

There are several other kinds of pants you can look into when updating or building your wardrobe. Some are good to have based on their versatility, but it is not essential that you go out and locate all of them. Khakis refer to 100% cotton pants made in the colour khaki. They are semi-formal to casual and can be worn to work and to other casual events/activities. Corduroys are pants that are ribbed vertically. They are more casual, as the material is thicker than the other options. They are not great for the hot summer days, but a date in the cool summer nights is the perfect time to wear a corduroy.

collage-Other Pants

Cargo Pants have external pockets and Velcro flaps. Although they are suitable for the man working in certain service industries that require him to carry various tools, cargo pants are often frowned upon in the workplace and are not suitable for dates. Chinos are often confused with khakis, but they are made with synthetic materials, tend to have a slight sheen to them, and are narrower and more tapered than the khaki. Chinos can be worn in the office as well as any other casual setting.


In the previous post we looked at the dress shirt for office wear. We said that men should look for long-sleeve dress shirts and avoid the short-sleeve version; we also suggest looking at the slim-fit dress shirts, as the regular or classic fit gives men a boxy look. For casual shirts, the rules are slightly different and non-existent in some cases. But to understand where the rules apply, let’s look at the styles of casual shirts.

When thinking of casual shirts, we’re talking about T-shirts, Henley shirts, polo shirts, casual collared shirts and more T-shirts.

collage-Casual Shirts

There are many variations of the T-shirt these days; some are considered super stylish, while others are boxy and look cheap. Fit and feel are important when it comes to T-shirts. Take, for instance, the lightweight, long-sleeve T-shirt shown above (the grey shirt to the extreme left). This lightweight T-shirt provides all the advantages of a regular T-shirt but in a stylish way that can be worn on many occasions. Similarly, the Henley Shirt (the second in the row) provides the same advantages with a buttoned fly by the collar. They are a great alternative to the T-shirt and can be found with long sleeves or short sleeves, and with a round or V-neck.

Graphic_Tee_with_Jeans_PS_largeA Graphic Tee, as the name suggests, is a T-shirt with graphics on it — not logos, but graphics. Graphic tees are more fitted than regular T-shirts, are made with a lightweight cotton material and are considered more acceptable for some events; T-shirts (like the one to the far right above) should only be worn for athletic or outdoor activities.

Polo Shirts are considered a great staple in any man’s wardrobe. According to Antonio at The Art of Manliness, “every man should own several polo shirts: one in white, one in a dark colour, and one with stripes.” Polo shirts can be worn almost anywhere: to the movies, to tea, to the beach, to work (on a Friday), to the club; you name it, a Polo can go.

The Casual Collared Shirt (fourth in the row above), is pretty similar to the dress shirts discussed in the previous post. They have a similar cut and feel and are considered more formal. The difference is that the casual collared shirt tends to have a bolder pattern, colour or style: i.e., double-breasted pockets, epaulettes or zippers, etc. These shirts, regardless of the style, can be worn anywhere, and with anything. Unlike the dress shirt, however, you can get the long sleeve or short sleeve in the casual collared shirt.

Again, the common mantra throughout is: “You will have to try on as many as possible to find your perfect fit.” If, for example, you’ve tried on a slim-fitted casual collared shirt and it feels tight and reveals too much of your belly, try to go up a size before disregarding the style altogether. The same goes for all the shirts mentioned above.


It’s not a little-known fact that women will have enough shoes to, as Jamaicans would say, “stone dawg.” We will have three different pairs of black shoes, all of which are to be worn at work. This does not include the black pumps we wear on special occasions — or, even worse, to a party. But for men, the number of shoes necessary for their wardrobe is significantly lower than that of a woman. Some would say a man only needs 5 pairs of shoes: a black pair of super-dressy shoes for formal events, a black and a brown pair of Oxfords for work (see previous post here), a pair of sneakers and a pair of boots.

collage-Casual Shoes for MenThat list is pretty simple and straightforward. There are, however, other shoes to be considered when updating your wardrobe. The Loafer, as previously mentioned, is a versatile shoe that can be worn to work and other semi-formal occasions. They are durable and comfortable and can be easily slipped on or off; they are perfect for the travelling professional.

Boat Shoes, on the other hand, are more casual than the loafer while providing the same benefits: they are comfortable, durable and slip-resistant and can be worn with shorts, chinos or jeans.

Cross Trainers are the perfect sneakers for the man who likes to stay in shape. They allow you to engage in a variety of outdoor activities and change up your exercise routine. Casual Sneakers, however, are more laid-back and casual but are a great substitute for your brown leather flip-flops.

“People tend to wear sneakers as an all-purpose shoe, but they are ill-equipped for many activities. Hence why you need boots.”


Rain Boots are strictly utilitarian, but in a country where we receive an average of 4 inches of rainfall every year, rain boots are becoming more and more essential. Granted, rain boots are not the most attractive boot out there, but in this case the functionality far outweighs their appearance. Just consider this: if you were stuck in Half-Way-Tree with 3 inches of water runoff, you would be happy with a pair of rain boots rather than your suede Desert Boots.

Speaking of desert boots, or Desert Clarks (as we like to call them), although casual in nature they are usually dressed up for a night on the town. For example, they can be worn to dinner, for seeing a show/play and for any other kind of weekend outing/activity. Also in the boot category are Hiking Boots, which are equipped for strenuous outdoor activities for which the sneakers and/or rain boots would not be appropriate. Lastly, Slippers or Flip-Flops (not sandals) are perfect for the home, the beach or going to a friend’s house; they are not appropriate for anything outside of that.


Yes, men wear undergarments, too, and for a lot of men they are as essential as a well-made suit. By undergarments I am referring to undershirts and merinos, boxers, briefs and boxer briefs.

“Undershirts are not about fashion; it’s about hygiene.”


Just as antiperspirants aid in limiting sweating and body odour, undershirts help in this regard as well. According to Cooke, a man should always wear an undershirt or merino under his dress shirts and button-down shirts, for this very reason.

As for the second kind of undergarment, Boxers are loose-fitting shorts that most men tend to prefer. Because of their loose-fitting nature, they are more comfortable and provide an ease of movement for men. They are, however, not suitable for physical activities and, according to Cooke, should not be worn under dress pants or trousers.

“Grown men should not wear briefs. Boxer briefs are barely acceptable. Man fi wear boxers.”


Briefs are close-fitting and tend to sit high on the waist, covering everything from the waist to the upper thigh. Briefs provide great gentleman support and therefore are suitable for sporting activities. Boxer briefs, as you’ve probably guessed, are the middle ground between the boxer and the brief. They are the same length as a boxer with the same close-fitting appeal of the brief.



It’s every bit a part of a man’s ensemble as it is for a woman. But unlike women, who can get away with big gaudy jewellery, the trick to wearing male jewellery is to KISS: Keep It Simple, Sweetheart. If, for example, your ears are pierced, your earrings should not be bigger than your girlfriend’s, wife’s, daughter’s or mother’s. It is not a competition. If you wear chains, avoid the clock-sized pendants like Flava Flav or Elephant Man’s necklaces. They are not your role models . . . right? Or are they?! Avoid the ostentatious styles or you will be viewed as pretentious and artificial.

Match your Metals. Always wear jewellery of the same metal. Never mix gold with silver, or platinum with bronze. That’s just not right. Instead, wear your golds together, and likewise for your silvers and any other kind of metal. Gold is easily translated to yellow and, as such, can be worn with warm earth tones like brown, green, cream, and deep blue and purple. Silver, on the other hand, is easily seen as gray and can be worn with dark colours such as black and gray, but you can also wear them with light colours during the summer months.

Copper or Bronze are seen as orange and can be worn with earth tones as well, but they are not as common as gold. Precious Stones like your birthstone should be kept to a minimum, as they are considered more feminine. Remember: no more than one stone in one piece of jewellery, like a class ring — that’s enough. Leather is a great accessory when it is kept in its natural earth tone (not dyed black). If you’re into leather accessories, nix the metal studs, unless you’re into goth. Wedding Bands and Heirlooms are the exceptions to these rules, though most male wedding bands are pretty simple. They are exempt from the mixing of metals and can be worn with anything.

Wear meaningful jewellery, jewellery that will be meaningful in the situation. And know when to wear what; save your best cufflinks, your favourite timeless watch, that classy silver bracelet, etc., for the big occasions in life. And remember to get your jewellery cleaned at least once a year. You can do an at-home cleaning, but taking them to a jeweller is the better option.

mens-hat-chart (1)Hats

Hats have always been useful and functional rather than fashionable. Hats protect you from the harsh rays of the sun, shade your eyes, keep your head warm during the winter and cool during the summer, and often save you from a bad haircut.

Hats also set you apart from the crowd. It is “better to be looked over than overlooked,” according to Las Vegas designer Nudie Cohen.

Hats are also “unique in their ability to communicate and convey respect for others,” Antonio at The Art of Manliness says.

When wearing a hat, remember to remove it when you enter someone’s house or office, during a meal, indoors at work and to show reverence.

Just to recap the main points and guidelines:

1. The slim-fit look is in; the big, boxy, blown-up look is out.

2. Try, try, try on every single thing until you’ve found the style and size that fit you perfectly.

3. It wouldn’t hurt to have an objective fashionable female present with you while shopping. She’ll guide you and ensure that what you’re wearing does and will look good on you.



I hope I’ve helped shed some light on the essentials for a man’s wardrobe and provided easy-to-understand guidelines for creating your personal style. This topic is far from closed, so if there is something you are not quite certain of, please feel free to let me know in the comments below. I would be more than happy to help.

P.S.: Thank YOU for stopping by . . . and if you want more inspiration, you can follow my Pinterest Board. 🙂

Related Links

How to Dress for the Weekend

The 100th Edition of Fashion Basics Part 1

Men’s Style Guide: 10 Ways for Rocking Jeans

Stylish Weekend Wear

9 Rules of Men’s Denim

Pants for Men: What You Need To Know

10 Shoes for Every Occasion

Back to Basics: Choosing a Casual Shoe

Shoes That Make The Man: Fall Edition

A Man’s Guide to Wearing Jewellery

Char Lesie