Dress Like a Man (9 page)

Take every item in your default outfit that doesn't serve an irreplaceable safety function, and think about how you can kick it up one small notch.

In some cases this can be as simple as making sure you've got a good fit and clean fabric. Here are a few examples of small, easy upgrades that won't ruin an outfits functionality:

• Blue jeans -- go with a dark shade of blue and spend a little more to get ones that fit nicely, even if your work is going to stain them. Then keep 'em as clean as you can, and bust out a fresh pair (or some khakis) when you're holding meetings or doing other non-manual labor.
  
• T-shirts -- upgrade to a button-fronted work shirt (short- or long-sleeved) with a soft turndown collar. Polo shirts are a slightly dressier option, if you're not worried about getting them dirty. If you run your own business, throw a company logo on there.
  
• Belts -- sturdy brown leather always looks more impressive than nylon webbing. Same goes for tool pouches and the like.
  
• Shoes/Boots -- go with rubber-soled, leather uppers work boots or work shoes. It's fine if they're scuffed up from work, but just like with the belt, leather looks a heck of a lot better than colored synthetic fabrics.
  

All of these upgrades will still function in a hands-on, physical work environment. They're a little more expensive to replace than plainer versions, but they're not any less useful.

When to Upgrade the Working Look

So when is it worth wearing slightly nicer clothes for manual labor?

Basically, when there's a concrete benefit in it for you. If it's just you and your work crew, hidden away somewhere, there's not much point. But you might consider going for a sharper style if anyone's going to be watching or evaluating you -- clients, bosses, potential customers, etc.

When you
shouldn't
bother is when it would actually impact your work, or make you look less prepared for it.

Because don't get us wrong -- you look better in clean, dark jeans and a polo than you do in overalls and a T-shirt. But if you're showing up to paint houses, and you know you're going to get covered in spills, wearing anything but your grubbiest and cheapest clothes makes you look wasteful and foolish.

So use some common sense. When you're mostly going to be walking, lifting things, measuring, testing, and doing other things that are hands-on but not dangerous or grubby, dress the look up a little. When there are environmental factors that could harm you or your clothing, forget about fashion and wear what works.

And when it comes time for a meeting, a project proposal, or something else that takes place in an office, rather than a job site, go ahead and throw a collared shirt and a sports jacket on. Can't hurt -- might help.

C
HAPTER 16:
D
RESSING
Y
OUR
A
GE

Should style change as a man ages?

In one sense, it doesn't matter if you think it "should" or not. A man's fashion is
going
to change, by virtue of his role in life and his budget, whether he wants it to or not.

Over a long enough lifespan, you'll also see fashion standards change fairly dramatically -- think about what twenty-somethings tend to wear today, versus what they wore fifty years ago. Plenty of men who were twenty in 1963 are still around, and they've seen a lot of change since then!

So to some extent you have no choice. But it's also worth a man's while to think about his age and how he can dress to flatter it specifically. Some looks just work better with a young face, or with gray hairs.

Men's Style - In Your Teens and 20s

The first adult years are generally not a time of custom clothing and high fashion, apart from a lucky few born into wealth.

Most men are going to spend their teens and 20s wearing whatever they can afford. That generally improves as the age range wears on -- guys in their late 20s typically have a lot more disposable income than guys in their early 20s, though there are obviously plenty of exceptions there.

A few things to keep in mind for dressing as a young man:

• In professional settings, it's better to overdress than not. Wear jackets and collared shirts a lot, and make sure you have good leather shoes. You're a lot harder to dismiss as some punk kid when you're dressed like a older gentleman.
  
• In your personal life, on the other hand, this is the time of life when you can be most experimental. Play around with different looks until you find the styles that suit you best. It's much less embarassing to have a fashion experiment go wrong on you when you're 20 than it is when your 50.
  
• Once you're out of college, ditch the styles associated with campus life. Hoodies with lettering and logos should vanish from your wardrobe, and you want to be pretty careful with things like jeans and flannels as well.
  

This is a time of transition, so make your changes as gradually as you need to -- but be focused on making them. Don't be complacent. Be adding to and improving your look now, so that you're not scrambling to dress your age a few years down the line.

Men's Style - In Your 30s

Traditionally, we think of men in their 30s as being men who are settling down into their places in life.

How true that is these days is sort of up for debate. The "traditional" model of manhood is hardly the only way of doing things. But no matter what you're doing with your life, your 30s is still not a bad time to be projecting an air of stability, or at least dependibility.

You're ready to stop being treated like a kid at this point. Your clothes should reflect that.

Don't be afraid to make some significant fashion changes as you hit your 30s and age through them:

• Do a thorough wardrobe cleanse and get rid of graphic T-shirts, hoodies, and anything else that just screams "college kid." You can keep an item or two for nostalgia (or irony), but they should be out of your regular clothing rotation for good.
  
• While you're at it, start pitching or adjusting anything that doesn't already have a custom fit. Again, a couple old favorites that hang sort of loose aren't a problem, but most of your wardrobe should be adjusted to fit you at this point.
  
• Invest in a few real wardrobe expenses. A couple pairs of high-quality leather shoes, some fashionable blazers; whatever strikes your fancy -- just have a few items that you're really happy with, even if it means spending a little more up front.
  
• Own at least one dark, business-appropriate suit, even if you don't need to wear it for your line of work. At this point in your life you're going to start getting invited places where you should really be wearing a decent suit, at least once in a while.
  

The 30-something man's wardrobe isn't really that different from the 20-something man's -- just a little more focused, a little better fitted, and maybe a little less varied now that you know the looks that work for you.

Men's Style - In Your 40s

A man's 40s are when the "you're not a kid anymore" thing really needs to be taken seriously.

No matter how well you've aged, no one's going to mistake you for a wild young buck in your 40s, and you don't want to give the impression that you're trying.

Instead, your 40s are the years to start cultivating a more refined style. Dress yourself a little nicer, spend a little more on clothes, and work on building a collection that's going to last, if not the rest of your life, at least a good chunk of it.

Rather than radically changing your style from your earlier years, work on making improvements in quality throughout your 40s:

• Add a couple really nice, built-to-last core pieces. Suits, shirts, shoes, outerwear, watches...whatever you're buying, buy it a little nicer than you're used to. Make a conscious effort to ratchet up the
  quality
  of the brands and materials you're buying.
  
• If you never have, go ahead and get something custom-made just for you. If you can't afford bespoke, go made-to-measure. It's still an amazing difference compared to basic off-the-rack stuff.
  
• Diversify your non-core wardrobe a little. Try out some new styles of shoe, for example, or of coats and jackets. Add accents you've never tried before. These don't have to be big changes -- just look over your style, think about what it's missing, and shake things up a little. You don't want to get
  too
  set in your ways.
  

This is a good age to be upgrading, refining, and personalizing your style. Be classy -- you're not a kid anymore -- but have a little fun with it.

Men's Style - In Your 50s

Ah, the 50s. Not retirement age, for most of us, but certainly moving toward thinking-about-retirement age, at the very least.

This is actually an interesting age, from a fashion standpoint. You don't want to be dressing like a young man, but you also don't want to signal to people that you're past your prime. It can be a delicate balancing act.

If you have a key word for style in your 50s, it should be
elegance.
This is the age when you want to look refined, confident, and in charge, without pushing to achieve it.

Key things to look for in your wardrobe when you're past 50:

• Invest in richness of color and texture. Go ahead and buy the good stuff, if you can afford it. There's a startling amount of difference between a high-quality Italian wool and whatever they're using this week at Men's Wearhouse. The drape of the fabric and the way the color sinks in are striking in a way that no fashion statement can be, if you get the right stuff.
  
• Extend that philosophy of quality to your smaller items, too. Never underestimate the power of a really good hat or even just a rich wool scarf to put your look ahead of everyone else's.
  
• Start thinking about upscale, sophisticated-looking styles. If you have to wear a suit, for example, consider a double-breasted or three-piece instead of the basic single-breasted model.
  

Depending on your career path, these may well end up being the most powerful and influential years of your life. It's worth dressing to reflect that.

Men's Style - In Your 60s and Up

Our society is not kind to old age.

Men in their 60s who don't take the time to dress sharp can easily find themselves dismissed from younger people's minds altogether. Once you've got gray (or no) hairs, wearing sloppy or battered clothing says "I'm done with life, you go on and don't pay any attention to me."

Cruel, but people are. So squash that train of thought before it gets started, and dress like someone who's active, confident, and important, whether you are or not.

Tips for guys in their 60s or older on the wardrobe front:

• Embrace the traditional looks. Casual "Sunday" suits, tweeds, checked trousers -- you're old enough now that no one can question your right to wear 'em. Go nuts with the old-school stuff. Just keep it high-quality and well-fitted.
  
• Velvet jackets. Seriously. You can get away with them now.
  
• If you find yourself needing a cane, make it a nice one. Similarly, if you need orthopedic shoes, go for ones with nice leather uppers. Needing a little help getting around doesn't have to look clunky, medical, and impersonal.
  
• Be cautious "dressing down." You really, really want to avoid things like tracksuits (unless you're actually running) and old sweatshirts. They present an unfortunate stereotype that you want to avoid.
  

Keep it classy and dignified in your 60s. Your clothing should claim a respected status, not an easily-dismissed one.

The Limits of "Dressing Your Age"

No written rule is going to apply universally to all men of a certain age.