Situation, environments, culture……all this goes into our personal style.
What I wear to a presentation during the summer is very different from what I wear around town during the cold winters as I taxi my kids to school!
BUT….if I had to layout the rules I follow……it would go something like what I have laid out in this detailed article.
It’s not the only way to think about style.
But it’s the way I’ve found best after years of experimentation, and it’s certainly a good starting place.
It all starts here.
If you don’t care how you look, you’re never going to look good. You can put on the best clothes in the world and you’ll still look like a kid dressing up for a school play.
Attitude is everything, in style and in life. I start my personal style journey every day by caring about who I am and what I represent — my business, my family, and my values.
2. Know Your History
This is an important rule for anyone who wants to really understand his clothes, as opposed to just trusting experts to tell him what to wear.
You could, for example, memorize the “rule” that trouser cuffs are informal, and that business suits should always be hemmed without a cuff.
Or you could understand the history of the trouser cuff — as a working man’s protection against fraying and mud, especially when working with horses and carriages — and know that its associations are with labor, not with business.
At that point you don’t have a rule to remember. Instead, you have an understanding of what your clothes mean, which in turn tells you when they would or would not be appropriate.
3. Don’t Be Afraid to Lead
I always tell my readers and my clients that they can’t be afraid to be the best-dressed guy in the room.
It takes getting used to. You may initially feel “overdressed,” particularly when you’re the only man wearing a jacket or a suit as opposed to a shirt or sweater.
Learn to embrace it. People may treat you differently — but the differences will be overwhelmingly positive. Turns out that most regular people assume a man in a sharp jacket or suit is someone important, and treat him accordingly.
That’s a good thing. It’ll open doors for you. But you do have to accept and embrace your new role as someone people look to as a leader, especially if you’ve never thought of yourself as one before.
4. Know Your “Why”
You need to know what you’re doing, and why. Otherwise you just end up looking silly.
I think “fedora guys” are a great example of why this rule is important. You probably know them — guys who own one black fedora, and wear it with everything.
They look out of place when worn like this. Sorry, guys, if you’ve ever done it, but there it is.
It’s not that you have to follow the rules all the time. It’s that you have to understand how the rules work in people’s minds, and what they’ll see if you break them. No one gets to rewrite style overnight. Even celebrities and designers get mocked if they push too far, too fast.
5. Understand Clothing Fit
This is my first rule for actually buying clothing: the fit of your clothing is its most important feature.
If you don’t have the right fit, everything else is wasted effort. Plain and simple.
Take the time to get to know your body, and have a tailor help you get accurate measurements. Learn to say “no” to clothes with a style you like, but a fit that can’t be adjusted to suit you. It really does matter.
6. Buy Clothing That Will Be in Style Years from Now
I like to focus on a “timeless style,” both in my personal life and in my advice to other men.
Certain looks are always going to be dependable. Men might not wear suits as much today as they did in our grandfathers’ time, but the suits our grandfathers wore would still mostly pass muster today.
I always urge men to focus on pieces that are both classic and associated specifically with men: suits, blazers, sports jackets, and trousers, both dress and casual.
Keep your look timeless and classic, both for your sake and your budget’s.
7. Buy the Best Quality You Can Afford
Treat your clothing like an investment. Look for a good return on your money. It’s better to buy one item that lasts ten years than ten that last one.A serious wardrobe requires serious budgeting. You don’t have to be rich, you just have to be realistic.
Realistically, if you aren’t drawing the kind of salary that would cover $5000 bespoke suits, you’re probably not working in an environment that expects them, either.
Spend the money you need to. If you’re traveling in high-powered circles, that’s going to be more money. If you’re upgrading a social wardrobe for hanging with your friends, it’s going to be less. Be sensible — but be willing to make at least a little bit of an investment.
Remember, the fit is everything.
8. Practice Wearing Your Best
The average guy doesn’t have a lot of ready-made excuses to wear a suit and tie. Unless you’re a lawyer or a banker, that’s an outfit that’s mostly reserved for special occasions.
If you don’t have business occasions to wear anything fancy, dress up for a social occasion. If you belong to a church, church services are always an appropriate time to wear a suit and tie (even if most of the congregation dresses to a more relaxed standard).
Even day to day errands like running to the grocery store can be done in a blazer, rather than jeans and a sweatshirt. There’s no law against being well-dressed at the supermarket. People will just assume you’re coming from some important meeting or other — and probably treat you with a little more respect without even realizing that they’re doing it.
9. Know Your Environment
Different situations call for different clothes. I love my worsted wool suits, but they’re not the right choice every time!
Physically, you want to be comfortable. That means lighter clothes in warm weather, thicker layers in cold, and a good fit all the time. Changing your wardrobe seasonally adds a little expense when you’re first building it, but over time you’ll end up saving wear and tear (and sweat damage) as you spread your usage out over more weather-appropriate options.
Socially, you want to look respectable at all times, without inviting trouble. And yes — wearing an expensive business suit to a dive bar in a bad part of town is inviting trouble!
Make the effort to fit in while looking sharp. That means jeans and even T-shirts, when jeans and T-shirts are appropriate. Just make sure they’re nice jeans and T-shirts: well-fitted, in good repair, and flattering to your body.
If you’re always wearing the same basic outfit, rethink your strategy. Odds are you need a little variation, in one direction or the other.
10. Buy Clothing That Is Interchangeable
The more of your existing wardrobe a new item goes well with, the more use you’re going to get out of it. Apart from those very purpose-specific outfits, everything I own is as interchangeable as possible.
This is very easy to achieve if you stick to simple, solid colors for most of your base pieces. There’s nothing wrong with a little pattern and texture here and there, but if you make sure that most of your big items aren’t overwhelming on their own, you’re free to liven them up with smaller accents when you want to make the look unique.
I think of it this way: if everything involved is interchangeable, then three jackets, three pairs of trousers, and five shirts gives me forty-five unique outfits (3 x 3 x 5 = 45). And that’s before I take belts, shoes, neckties, and other small items into account!
It never works out quite that perfectly, of course. There are always some matches that just don’t quite work. But if your items are interchangeable, every new one has a multiplicative effect on your wardrobe instead of an additive one.
There you have it — my rules for dressing well! I hope they help you on your own style journey.