Rules for dressing well exist for a reason. This may not be clear to us as boys when our fathers instruct us on the importance of wearing a blue blazer. But they make sense over time, and we realize that certain enduring principles help men look terrific. That’s made easier by the fact that men’s clothing is quite straightforward, which is why if you dress like Fred Astaire, you’ll still look very smart indeed.
Illustration by Hilbrand Bos
In general, trends send men in strange directions against their better judgment. Skinny jeans come along and addle our legs and our minds. Single pleats go away, replaced by flat-front trousers, but wait, what’s this — stylish men are wearing double-pleat trousers? Back to the drawing board. There are new fabrics, and while some are good, anything ending in an “x” should make you think twice.
Ultimately, we look to rules because guidelines are useful guardrails. You can steer clear of them or crash into them, but it’s important to know they’re there. Most well-dressed men I know indeed break a rule or two, but they’ve earned it. And you can earn it, too. Here are 10 defining style commandments to dress by.
David Coggins’ 10 Style Rules
Illustration by Hilbrand Bos
1 | Let Your Clothes Serve You
The first thing to note is that clothes should flatter you. They should express your personality and your worldview all while fitting well. So consider your size, your eye and hair color, and how you want to fit into society. These things evolve but don’t change too drastically, which is why when you arrive at your personal sense of style, it’s a good thing to hold onto it.
2 | Respect Proportion
You’re tall, you’re stocky, you’re some other adjective of distinction. Your clothes can help accentuate or hide what’s worth accentuating or hiding. Here, I’ll go first: My head is big. There I’ve said it. It may be because it’s full of ideas or maybe not, but it’s a fact. That means a sport coat with narrow lapels will make my large head look even larger, like a balloon that might float away, and nobody wants that. A while back, every man wanted to look like he walked off the set of Mad Men, and lapels became very narrow. That works for Don Draper, but sadly, I’m not Don Draper. So try to find clothes that are in harmony with your figure. Smaller, trim men look better in concise, tidy proportions. Larger men can handle clothes cut more generously.
3 | Know a Tailor
In a perfect world, you’re friendly with a tailor. You know what he does well, and he knows what you wear well. That’s a beautiful relationship, as important as knowing a good bartender, psychoanalyst or fishing guide. That also takes time, money and proximity. If you don’t have a tailor, then get to know someone you trust for alterations. Good alterations are as important to clothing as good editing is to writing: The basics are there; it just helps with the shape of things. The sleeves of your jacket too long? That’s no surprise, because most men wear their sleeves too long. Your tailor can help. Have thoughts on the break of your trousers? You should, because you don’t want cloth pooling around your ankles. Again, a tailor can save the day. Also, they can let out our waistlines — no shame there! — because if your ancient clothes don’t fit, you have two choices: get them sorted out by a tailor or donate them to charity. (There’s no third way.)
4 | Fear Not the Suit
There is nothing banal about a suit; it simply needs to be cut well and worn even better. How does this happen? Buy one from a man who’s wearing a suit and looks good in it. A suit should be comfortable, with high arm holes that allow for easy movement through the shoulders. It doesn’t need too much construction (the padding that’s a hallmark of very traditional English suits), so probably an Italian suit. Start with classics: charcoal or a deep shade of blue. There’s a reason these colors are available at Ralph Lauren every season, year after year. Then go from there. The suit is a criminally overlooked aspect of the sartorial arsenal. A suit is not middle management; it’s boss.
5 | Invest in a Tuxedo
By definition, a black-tie event is important, and naturally you want to look good. Even if you’re attending opening night of a Wagner opera against your will, you want to be an attractive date for whoever your attractive date is. Yes, you only need to wear it rarely, but you’re a grown man and grown men don’t rent clothes. One word of advice: If your tuxedo is neglected in the back of your wardrobe, take it out for a test drive before the big event. Tuxedos have been known to shrink from years of disuse, so to speak, and hearts have been broken when a man tries to squeeze into an ancient once-fitting tux an hour before heading into public.
6 | Buy Good Shoes
Well-dressed men wear good shoes. That’s a fact. Good shoes are not sneakers, which are for boys. They’re leather and expensive, because there’s not a good way to make them cheaply. They’re usually English (Crockett & Jones, Edward Green, Lobb), but they can also be American (Alden). They’re cordovan brogues, suede chukka boots, nice loafers with or without tassels. Keep them polished or wear them rakishly scuffed, but accept no substitutes.
7 | Be in Season
Clothing reveals who you are, naturally, but it also reveals when you are. You’re a man for all seasons, and your clothes should celebrate the heat of July or the chill of December. The same way you drink gin in the summer, which feels like a white linen jacket, you drink whiskey as the days get shorter and don a shawl-collared cardigan by the fire. I love seeing a man on the street who embraces the conditions, even when the conditions aren’t optimal. Style in a rainstorm is true style.
8 | Add Some Texture
Texture brings richness and depth to your clothing. This is particularly true of suits and sport coats, which look great when they have a little tooth to them. Once you know what colors work for you, seek them out in tweed or corduroy. What could be more elegant than a gray flannel suit with a white oxford cloth shirt and a beloved silk knit tie? Wear a combination of textures in a single tone, and you’ll come across as the sophisticated man you are.
9 | Embrace Eccentricity
There is nothing wrong — and in fact there’s a lot right — with a strong attraction to something singular. So let’s raise a glass to your white bucks, your velvet jacket, your seersucker suit and everything else with outsize character. What’s the secret? Conviction and repetition. If you’re concerned about getting away with something, wear it around the house until you feel ready to face your adoring public. The first time you wear your Panama hat, you might meet minor opposition. The second time, people will understand what you’re driving at. By the third time, it’s your signature look and nobody can remember you without it.
10 | Set the Standard
Your clothes communicate something about you whether you want them to or not. And you don’t want to communicate that you are on your way to or from the gym. There are very few rules that are truly unbreakable, but here’s the cold hard truth: No man has ever looked good in sweatpants.
A Minnesotan turned New Yorker, David Coggins is the author of the New York Times bestseller Men and Style and writes a style column for Artful Living.
