Have you ever noticed a well-dressed man and thought, “I wish I could look that good”? Here’s a secret: you can.
Dressing well is not rocket science. True, there are many rules and reminders to follow, but you too can learn how to dress well without driving yourself mad or breaking your budget.
We’ll show you how with our 10 commandments for dressing like a man that will have others wondering how they can look as good as you. And then you can let them in on the secret.
How to Dress Well as a Man: The 10 Commandments (A simple, illustrated guide)
1. Thou shalt get the right fit
OK, so one of the commandments for dressing well should have a biblical reference and we might as well make it the most important one.
While it’s true that all the commandments on this list are of vital importance, getting the right fit is crucial for dressing like a classic man, or any man for that matter.
The highest-quality, most expensive clothing won’t look good if it doesn’t fit. It may look terrible, for that matter.
The following are tips and suggestions for making sure that you always get the right fit to ensure that you look the best you can.
- Learn your measurements – Get measured by a tailor, if possible. Men often buy suits that are too large, as much as two sizes too large, and you’ll avoid that blunder if you have your precise measurements in hand.
- A good fit 101 – If your clothing sits close to your skin without pinching or constricting your movement, then it’s probably a good fit. Your pants can be a bit looser than your shirt, but don’t let them become too baggy.
- Bring your shoes – Bring your dress shoes, or the shoes you most often wear, with you when trying on pants. You’ll be able to measure the pant length accurately at the place where it falls on the shoe.
The way your clothes rest on your body affects their – and your – appearance a great deal. And there’s a lot to be said about fit:
- Dress shirts – The collar of a dress shirt is too tight if your collar turns with your head. The cuffs should extend to just above your wrist bone and have a slightly looser fit and feel of a watch. The sleeves shouldn’t be so tight that they expose your arm’s details, but they shouldn’t be overly baggy either. Meanwhile, the shirt should be long enough that it doesn’t come untucked when bending or making other natural movements.
- Dress pants – You should wear dress pants that have a single defined creased down the middle of the pant leg. You want your dress pants to fit comfortably close to the leg without billowing.
- Jeans – Choose a straight leg or slimmer fit. The fit should be slimmest in the thigh and tapered or straight beyond the knee. The length of your jeans should vary depending on if you plan to cuff them.
- Chinos – Like dress pants, chinos should fit comfortably against the skin but not so tight as to cause resistance. The waist should fit snug enough that you don’t need a belt to keep them from falling to your ankles.
- Suit jackets and blazers – The shoulder seams of a suit jacket or blazer should lie on the edge of the shoulder to reduce the amount of buckling or wrinkling while your arms are at your sides. The jacket shouldn’t pull across your chest (in which the fabric makes an ‘X’ shape), or across your shoulder when your arms are folded. The sleeves should cover your wrist bones while a suit jacket’s length should cover your buttocks.
- Tie – Many men fasten their necktie as it were a noose, cutting off all blood flow at their throat and neck. OK, maybe not that tight, but the point is that the tie should sit comfortably under your collar without tightening it. The width of the knot depends on the width of your collar; a wider collar calls for a wider knot and vice-versa. Always pay attention to the length of the tie, too: the bottom of it should reach the center of your belt when you stand straight.
2. Know your style
Defining your signature style is an important part of dressing well but it’s not easy. You need to have plenty of self-knowledge and to be honest with yourself. A style or manner of dress that suits your colleague, friend, or favorite celebrity, may not suit you.
So, what to do? Here are some things to keep in mind:
- Your body shape – Certain styles look better for your body shape than others. Don’t become attached to the idea that you can wear anything and everything.
- Your job – A lawyer or banker in a large city dresses differently than, say, a home inspector or fishing cruise captain.
- Weather – Your environment is another important factor for dressing well. A man who lives in a wintry climate, or at least one that experiences harsh winters as a matter of course, should dress differently than a man who lives in Hawaii. Heavier wools work well in cold weather while cotton suits warmer climates.
- Watch what others wear – While a certain man’s style may not suit you or your body type there’s nothing wrong with keeping a close eye on what other men wear. Take cues from another man if you think he rocks his style to the fullest. Adopt the cut and colors of their clothes if they work for you.
- Choose the right colors – We’ll talk more about color in a bit but choose colors that suit your style and skin complexion.
- Your age – It’s always a bit creepy when a 50-year-old man walks into a club dressed like a 20-year-old. Don’t be that guy.
3. Know the occasion
No one wears flip-flops to a black-tie dinner. Or, if they do – well, you can imagine the reaction.
The point is there’s always the right time and place for an outfit. Dressing well also means dressing appropriately for the occasion.
You don’t want to stick out like a sore thumb at an event because you’ve over or underdressed.
You don’t want to go over-the-top with an outfit or accessories when the event is decidedly casual, nor should you be the underdressed person who looks like he doesn’t respect the formality of the event.
Always think about where you’re going. Does your office have a dress code? Is it a job interview? A wedding?
Understated is typically a safer bet than overstated. You want to look good, but you shouldn’t overdo it and seem like you’re trying too hard to impress everyone. If you’re unsure, don’t be afraid to ask someone who knows.
4. Choose your colors carefully
Proper color coordination is among the most important men’s dressing tips. Even the priciest, best-fitting clothing in the world won’t look good if the colors don’t match or coordinate.
Among the fundamentals of properly wearing colors is that neutral colors are almost always best.
Yes, you can make your wardrobe look bold with bright vibrant colors but, in most cases, they’re not appropriate to the occasion, and they’re harder to pair with the rest of your wardrobe.
Neutral colors include black, white, grey, navy, tan, brown, cream, khaki. Olive is another neutral color that looks good without calling too much attention to your wardrobe. Plus, you can combine neutral colors with brighter colors (but bright on bright not so much).
In general, a less-is-more approach is always important regarding color. One nice “pop” or color per outfit is fine, but don’t overdo it. And, relying on certain color combinations can help you dress well without looking too bright or too bland:
- Navy and white
This is a can’t-miss combination that works for almost every occasion. The contrast between blue and white is pronounced, which helps make it pop, and you can make it work with a variety of clothing styles and types.
- Black and white
It doesn’t get more classic than a black and white color combination. It’s an elegant, clean look, albeit one that is a bit more formal than other color combinations. But it all depends on how you wear it.
- Gray and black
You should seriously consider adding a gray and black combo to your wardrobe if you don’t already have one. It represents a subtle variation in color that offers a nice, muted contrast. Wearing a dark gray polo shirt with black jeans is one way to capitalize on the two colors.
- Brown and cream
The brown on cream on a lighter tan look is decidedly laid back and looks damn good whether you’re hanging out in warm weather – like on a pool deck.
There are other combinations, such as khaki and green and brown and burgundy that also work well in your wardrobe. As far as bad color combinations go, well, here are a few:
- Red and orange
Red and orange just look too bold when paired together.
- Red and green
Save red and green for the Christmas season, if even then.
- Green and orange
Orange is loud while green is a neutral shade that has enough color in that you shouldn’t dull with a louder counterpart.
- Brown and black
Nope. Don’t do it. While some men can pull it off, the brown and black combination is one that never gets any kudos, and with good reason.
Meanwhile, choosing the color of your tie all comes down to your shirt.
You can wear a contrasting color to added little life to a solid-color dress shirt, while a darker tie in a complementary color helps to create a nice look with a lighter color shirt. A patterned tie looks good with a solid dress shirt, as well.
A solid-colored tie is a safe bet with a patterned shirt that has multiple colors. And it doesn’t hurt if one of the colors in the pattern matches the color of your tie.
5. Build a versatile wardrobe
You can look good, damn good, without a closet that’s overflowing with clothing items.
The key is versatility, i.e., to have several pieces that work with many complementary items. If you have a shirt that matches most of your pants, then it’s highly versatile and interchangeable.
Or, if you have a suit and blazer that pairs well with most of your dress shirts, you’ll reap the many benefits of versatility.
Well over half of your wardrobe should consist of classic interchangeable pieces – the higher compatibility the better.
A versatile wardrobe means less clothing in your closet and less money spent on clothing.
Purchase core wardrobe pieces, such as a dark suit, blazer, or sports jacket, leather dress shoes, a variety of solid color dress shirts, gray pants, dark Levi’s, and more.
In general, most of your pieces should feature a neutral, solid color, while the fabric should be of a medium weight that’s more interchangeable than light or heavier weight fabrics.
6. A suit and blazer can make the man
No man’s wardrobe is complete without a good suit or blazer (or both). A suit enhances your look, gives you confidence, and makes it clear that you know how to dress like a man.
A suit – or blazer – looks terrific on any man, and is versatile enough to wear to the office, a business casual setting or event, or a fancier occasion that requires formal wear. But, like any men’s apparel, there are a few rules of the road to follow when wearing a suit:
- Dark colors, such as charcoal, black, or navy present a timeless, classic look. But color coordination is the key – no matter what color you choose – and you should make sure your shoes complement the color of your suit, and that your shoes match your belt, among other rules.
- Again, the fit is crucial for every part of your wardrobe. The fit of your suit jacket should be form-fitting, so you don’t look like you’re swimming in an over-abundance of material. It should properly hug your shoulders, and the sleeves should stop before your shirt cuffs because you want a bit of your shirt to show.
- A suit jacket that wraps around your mid-section while leaving stretch creases is too small.
- Pairing a suit jacket or blazer with jeans is a classic smart casual look that never grows old. Just make sure that you don’t wear baggy or ripped jeans.
- Blazers are incredibly versatile and add a bit of formality to an otherwise casual wardrobe. You don’t need to wear matching pants with blazers, as you do with a suit jacket, and you can pair a blazer with everything from t-shirts, dress shirts, jeans, chinos, sneakers – and more.
7. Never underestimate the importance of your shoes
Stylish men always regard their footwear with the same importance as they do the rest of their clothing.
The old saying that “you can tell a man by his shoes” isn’t one to take lightly, especially when you consider how the wrong shoes can spoil an otherwise fashionable outfit.
There’s a lot to keep in mind when deciding what type, brand, and style of shoes you should wear, including the occasion – of which we just finished discussing. You shouldn’t wear athletic shoes to the office, unless your office’s dress code permits it.
A good pair of quality shoes, such as dress shoes for the right occasion, complete your outfit but also should be constructed in a way that keeps your feet comfortable throughout your day.
You can expect to pay more for the best shoes and shoe brands but it’s almost always a worthwhile investment. A pair of shoes made from quality leather should last you a long time (you may have to re-sole them from time to time) with proper care.
Whatever style you select, keeping them in the best shape is essential. Your shoes will not only last longer, but they’ll always look good. Never let a scuffed or poorly maintained shoe detract from your look.
8. Use accessories wisely
The right accessories can dress up and enhance an outfit’s appearance. You can add some zest to an otherwise boring outfit with accessories such as watches, sunglasses, ties, suspenders, pocket squares, and more.
Be careful that you don’t go overboard with accessories, however. A wardrobe that features an overabundance of accessories can look more like a costume rather than a classic, versatile style of clothes.
A couple of accessories – say, a watch and sunglasses – is enough to add some taste and style to your outfit. Less is more is true in most cases.
9. Rely on a tailor when needed
Another great way to enhance your style – while looking like the best-dressed man in the room – is to rely on a tailor’s expertise. The benefits are many, including:
- Your suit will look fantastic
A well-tailored suit kicks ass in a good way. You’ll get the right fit, for one, and that’s essential if the suit you choose off the rack fits OK, but not as well as it could. Often, those suits are slightly big, and a tailor can alter it so that it accentuates your build.
The tailor can modify everything, from the sleeves to the shoulders to the length to turn a slightly “sloppy” suit into a work of art.
- It’s a wise investment
Sure, the cost of a good tailor isn’t cheap, but he or she may save you money in the long run. You may have clothes that just don’t fit or look right anymore, which prompts you to buy new clothes, while a tailor can often alter the clothes you have.
You’ll look good and get more use from your clothes.
Clothes never quite feel comfortable when their fit varies from one area of the body to the next. A tailor can adjust the fit so that comfort becomes second nature.
- Your clothes will complement your body shape
Body shape is an important consideration when buying clothes. You may never find the “perfect” fit for your body without the help of a tailor, who will take your precise measurements and alter the clothes accordingly.
Here’s the other thing: tailoring will accentuate the parts of your body that look best while hiding the parts that you’d rather leave less conspicuous.
10. Shop accordingly
Unless you buy on impulse, which we hope you don’t, you should have a plan before you shop for new clothes and spend your hard-earned money.
So, before you go on your next shopping trip, take stock of your current wardrobe, i.e., what you have, what you like, what you dislike, and what you think you lack. Doing so will help you to develop a plan and strategy for shopping.
Also consider factors such as your style and personality, your work environment, whether it coordinates with other pieces in your wardrobe, whether it’s best worn for a certain season or whether you can wear it year-round. Do the clothes inspire you?
You’ll want to consider your budget, of course, and should shop for versatile clothing that pairs well with other clothes you already own, and that has a reputation for excellent craftsmanship and durability.
Dressing well doesn’t have to be complicated because, in many cases, a less is more approach is best.
There are several things to keep in mind, as we list above, but once you get the feel and sense for what works for you and your style you should be able to create a classic-yet-modern look effortlessly.
What are some styling rules and tips you follow? What clothes are staples of your wardrobe? We’d love to hear from you.