10 Style Rules To Live By – Ten Timeless Fashion Guidelines For Men

People often ask me what MY personal style rules are.
This is hard – as what they are really asking is:
Antonio – can you tell me exactly what to do so I don’t have to think about it.

Unfortunately it’s not that easy.
Situation, environments, culture……all this goes into our personal style.
What I wear to a presentation in Las Vegas during the summer is very different from what I wear around town here in Wisconsin 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.

Again, these are the “general rules” that guide my personal style, and my writing on style for others.
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.

For a video summary of my 10 style rules for men – click here!

1. Give a Damn.

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 giving a damn about who I am and what I represent — my business, my family, and my values.
Caring about those things strongly makes me care strongly about how I present myself. I give a damn. I dress like I give a damn.
It all starts here. And without this rule, no one’s ever going to get much of anywhere — in improving his wardrobe, or in anything else.

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 need to have a little understanding of (and respect for) where modern styles came from.
That’s both a philosophical and a practical consideration. If you just try to memorize “do and don’t” rules, it gets overwhelming. There’s too much to handle.
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.
So with all of my outfits, I strive for an understanding of the style’s history. Where our clothes came from matters, and it still influences the messages they send today — whether the people receiving the message understand why or not.

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.
Because I’ll tell you what — if you take the time to care about your appearance, it’s going to happen.
And that’s not a bad thing.
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”

This is a lot like my rule about knowing your history.
Fashion doesn’t have a lot of fixed yes-or-no rules. And the few that it does have can be broken stylishly (and have been).
But 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.
That’s because fedoras are dress hats. They’re deeply associated in our minds with suits. Wearing one with a T-shirt doesn’t make you look like an innovator — it makes you look confusing and a little off-putting to people’s habits of thought. And wearing one all the time tells people that you don’t understand any other headgear options.
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.
Have some respect for the existing traditions. They’re there for a reason.

5. Understand Clothing Fit

This is my first rule for actually buying clothing, and I’ve said it many, many times here on this site and elsewhere: the fit of your clothing is its most important feature.
Not everyone wants to hear that. It’s not the most glamorous aspect of fashion. There are lots of numbers and measurement, and it can seem kind of boring.
But trust me on this one — the most expensive suit in the world isn’t going to look good on you unless it fits your body right.
If you don’t have the right fit, everything else is wasted effort. Plain and simple.
A good fit should flatter your body. It will draw attention to the parts of you that you want to highlight (usually the face, chest, and shoulders), and it can also minimize aspects you’re not as fond of (a large midsection, for example).
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.
That’s a goal worth striving for: having clothing that your grandchildren could wear fifty years from now without looking out of place.
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.
Steer clear of exaggerated trends and “this year’s hot looks.” Think about some of the trends that defined earlier eras: huge lapels, ultra-skinny ties, padded shoulders, and so on.
You wouldn’t want to wear those today. They’d look dated and awful. So why wear this year’s equivalent? It’ll be just as outdated in a few years. 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.
That said, I do always stress the idea of buying the best clothing you can afford. Not everyone needs luxury tailoring!
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. There’s nothing wrong with wearing made-to-measure, or even off-the-rack clothing adjusted by a tailor.
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.
A clever shopper can look like a high-powered exec in nothing but thrift-store castoffs and ready-to-wear retail clothes. It just takes time — and adjustments by a skilled tailor! 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.
Get in the habit of wearing your best clothes as a matter of routine, and it’ll take a lot of the mystery (and the mental resistance) out of dressing well.
It’s easy to get into a mental paralysis with good wool jackets and slacks. They’re expensive, they’re a little harder to maintain than cotton shirts and jeans, and they make us feel more out of place. Try to teach yourself that they’re just clothes — clothes that look good on you.
If you don’t have business occasions to wear anything fancy, dress up for a social occasion. If you belong to a church, Sunday morning services are always an appropriate time to wear a suit and tie (even if most of the congregation dresses to a more relaxed standard). Evenings at the theater or sit-down musical concerts (not rock concerts!) are similarly good occasions to break out your best.
Even day to day errands like running to the grocery store can be done in wool slacks and 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!
A good dresser keeps his environment in mind — both the physical and the social aspects of it.
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.
That’s a principle that’s guided my style (and my style advice) for years. I try to stay away from anything that’s completely single-purpose, with one or two unavoidable exceptions like tuxedos. Apart from those very purpose-specific outfits, everything I own is as interchangeable as possible.
That way I can mix and match to get more mileage out of individual pieces. A dark blazer that goes with gray wool trousers is great. If the same blazer also looks good with jeans, so much the better!
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.

My Style Rules

So there you have it — my top ten style rules. Those are the ones I follow personally, and the ones I use to guide my own wardrobe choices. In list format, they are:
1. Give a Damn - Care about your appearance.
2. Know Your History – Be aware of the menswear that came before yours.
3. Do Not Be Afraid to Lead – Know that sometimes you’ll be the best-dressed man in the room.
4. Know Your Why – Realize that “rules” are there for a reason, even if they can sometimes be broken.
5. Understand Clothing Fit – A good fit should always be your first priority when purchasing new clothing.
6. Buy Clothing That Will Be In Style Years from Now – Avoid temporary trends and fluctuations of fashion.
7. Buy the Best Quality You Can Afford – Treat your clothing like an investment, and shop slowly but smart.
8. Practice Wearing Your Best – Make excuses to wear the good stuff, instead of letting it get dusty in the closet.
9. Know Your Environment – Dress appropriately, whether that means dressing up or dressing down.
10. Buy Clothing That Is Interchangeable – Expand your wardrobe with clothes that work together, not standalone pieces.


There you have it — my rules for dressing well! I hope they help you on your own style journey.