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How To Dress For Your Age | Appropriate

Styles For Men Of Different Ages | Dressing
For Your Age
Shakespeare listed seven ages of man in As You Like It, but happily we only have to dress
ourselves for three or four of them.

There's a dignity to dressing your age that cuts both ways. A balding man with a gray beard who
wears board shorts and an Abercrombie polo is just kidding himself, but so is the college student
in a $3000 bespoke suit. Both of them are reaching for something they can't attain.

I don't want to lay out absolute brackets here, and I wouldn't expect you to take it seriously if I
did — there's no rule that says you turn from a “Young Man” into a “Professional” at age 21;
throw out your wardrobe and buy a whole new one.

The Young Man: 18-35

A full head of ungrayed hair and a body that stays in shape with unfair ease goes a long way in
fashion. Enjoy them while you have them.

Apart from the physical advantages, the “young” look is de ned by experimentation, variety,
and a touch of aggressiveness as far as bucking the traditional look goes.

Of course, knowing when to experiment and when to fall back on the timeless still becomes
more and more important as the young man ages; a college boy of 19 is far less likely to need a
sharp-looking suit and the practice to wear it con dently than a young professional of 32.

Casual Dress for the Young Man

Young men can usually wear just about any style as long as they're willing to really own it. That
means no half-measures — funky, bright-colored trousers mean a mix-and-match look in the
rest of the out t; don't pair them with plain black dress shoes and a pressed white dress shirt.
You'll just confuse people.

#1 Pick One Image

You want an out t that can be described in one word. (This is good advice for all ages, but
especially helpful for young men, whose wardrobes tend to be more varied). Do you look
“preppy?” “Grunge?” “Hipster?” If you're looking like a little from each all at once you probably
need to change some items around.

#2 Vary the Look

Youth is about experimenting. If you're the guy
who always wears khakis and a polo, you're
doing “young” wrong. Play around a little. I've
never met a stylish young man who didn't have
a wide variety of tops and trousers (to say
nothing of accessories) in the closet.

Varying the look from day to day keeps you

from being pigeonholed. Dress classic-sharp
one day with a tucked-in dress shirt, slacks, and
a dark blazer, then switch to bright corduroys
and a graphic T-shirt under a zippered hoodie
the next. And so on.

#3 Accessorize to Make the Look “Deliberate”

What's the difference between a guy in jeans

and a hoodie with ip- ops and a guy in jeans
and a hoodie with bright white bucks?

Quite a bit, actually.

Having an eye-catching accessory somewhere

in an out t makes it clear to people that you're
wearing a deliberate “look” rather than some
mismatched pieces grabbed at random out of
your closet.

This is especially important for casual out ts,

which can look like the careless sloppiness of
callow youth if you're not careful. Sharp-
looking accessories mean that even if the older
generation doesn't like your style they still have
to at least concede that it is a style.

Casual Clothing For Young Men

1) Dark, well- tted blue jeans, the always-
acceptable casual staple. Go ahead and invest a
little extra to get a pair that ts well and is a
nice, deep indigo rather than light blue.

2) A light-colored blazer and a dark-colored

blazer, nice and casual.

3) Some brightly-colored pieces, anything from

T-shirts to trousers and jackets. Try not to wear
them all in the same out t, but use them to
liven up an otherwise-conservative out t.

4) At least one pair of plain khakis or slacks and a dress shirt that you can wear when you go to
church with Grandma (or whatever other casual-but-conservative events come up in your life).

5) Belts. Wearing trousers with belt loops and no belt just looks sloppy.
6) A couple pairs of funky shoes. Colored canvas sneakers, decorated leather brogues and
saddle shoes, espadrilles, moccasins — whatever you feel like. But some options that aren't
sneakers or plain black/brown dress shoes are key.

7) Some brightly-colored or patterned socks never hurt either, while we're on the subject of
feet.

Business Dress for Young Men

As you get out of school and into the business world the need for conservative trousers, dress
shirts, and blazers increases. At least one actual suit becomes something of a necessity as well,
for interviews if nothing else. In many cases these are unfamiliar articles of clothing — a good t
and attention to the basics are key to looking like a grown man, rather than a schoolboy in his
dad's old suit.

#1 Good Fit Above All Else

Ready-to-wear suits are made deliberately big. This lets stores sell them to a maximum number
of men, but is bad news for t younger men. A loose, baggy suit jacket paired with a young face
is the easiest way to look like a kid in borrowed clothes.

Whenever possible, shop for jackets and trousers at places that do in-house adjustments. If
necessary, take them to a tailor as well. The t should be closer than an older man's. Don't wear
anything so tight it pinches, but avoid any loose cloth hanging off the body when the garment is
properly-buttoned.

#2 Keep it Simple

There's such a thing as a business-dress suit with a distinct pattern or unusual features, but on a
young man it's likely to look more like an error made in ignorance than a conscious style choice.

Stick to basic styles like the two-button, single-breasted, notch-lapel business suit in a dark
solid. Leave the three-piece, padded-shoulder, peaked-lapel, pinstriped charcoal suits for men
who have the gray hairs to carry them well.

#3 Err on the Side of Overdressing

A young man who wears a suit and tie when everyone else is wearing sports jackets and open
collars looks like he's striving to impress. A young man who wears a blazer and khakis when
everyone else is in suits looks like a kid who can't be taken seriously.

You're always going to be better off looking like you try too hard than looking like you don't try
enough. When in doubt, wear the suit. You can always take your necktie off and tuck it in a
pocket if you nd yourself badly overdressed. If you show up underdressed, there's no remedy.
Business Clothing For Young Men
1) At least one suit. A simple single-breasted model in charcoal gray or navy blue is best, and the
t should be adjusted to keep it close to the body.

2) A navy blue blazer. It goes with everything and is always respectable. It can also be paired
with unusual shirts or trousers for a funkier look in the evening.

3) A plain white dress shirt, spread or point collar (not button-down). For the most formal
business settings.

4) At least a few collared dress shirts, lightly colored or patterned.

5) A minimum of three or four neckties, including a few conservative ones in dark colors with
modest or no patterning.

6) A pair of plain black oxford balmoral shoes, well shined. A second pair of brown leather
oxfords or bluchers is also worth having for more casual business wear.

7) Medium gray wool slacks. They're the navy blazer of the lower body — versatile and
functional with almost any look. And, of course, they can indeed be paired with a navy blazer.

8) A plain black leather belt and a plain brown leather belt. Your leathers should always match,
and a ratty belt ruins the fanciest suit.

The Professional Man: 25-50

Alert readers will already have noticed that our age bracket for “the Professional Man” overlaps
with the age bracket for “The Young Man.”

That's deliberate. Surely you've heard of young professionals?

But there is a transition point; it just comes at different ages in different men's lives. At some
point you go from being a man who's trying different careers, interviewing often, and
experimenting with life to someone who's got a path pretty well gured out and plans to keep
working at it. Fashion changes accordingly.

Don't break out the walker and Geritol just yet. Being a professional man doesn't mean it's time
for tweed jackets and high-waisted stretch pants. But it does mean a transition from more
aggressive younger men's styles that say “look at me!” to the restrained elegance of a man who
feels con dent about his place in the world.

Instead of “look at me,” a professional man's clothing should say “I know you're looking at me.”
It's all about con dence of assumption.

A little honesty also goes a long way. When your waistline starts to expand and your hairline
starts to recede, change your style accordingly. Trying to wear the clothes you wore fty pounds
and a different hair color ago is unlikely to atter you.

Casual Dress for the Professional Man

Days and evenings off aren't entirely free time for most working men. You never know who
you're going to run into, and appearances still matter. Stocking the closet with comfortable
casual clothes that actually look good — rather than relying on work jeans and T-shirts — keeps
you prepared without having to work at it.
#1 Raise the Standard

Training yourself to dress well is easy: it

requires you to only have good clothing.

Easy, right?

Most men's default wardrobe can use a raise in

standards. A pair of jeans or two is ne
(especially dark, tted jeans), but you should
have just as many cotton slacks, and just as
many wool trousers beyond that. A variety of
colors keeps you varied as well as dressy.

Shirts should get the same treatment. Once

you're past 25 or so there's really no room for
T-shirts outside of exercise and physical labor.
The majority of your casual shirts should have collars. Your stepping-outside out ts should
almost always be something that would look good if you threw a sports jacket on over them.

And speaking of that, a professional man's closet needs casual jackets. Several of them. The
tapered shape is going to atter your body, and by stepping up the formality a notch you're
showing everyone that you can afford to dress well for pleasure as well as business.

#2 Moderate Your Colors

Neon orange corduroys are a young man's indulgence. As you age and settle a bit in life you'll
want to tone it down a notch.

That doesn't mean you should stop wearing a variety of colors. In fact, a professional man
bene ts from a wardrobe made up of many different colors (it keeps regular work wear from
looking uniform), but the colors shouldn't be the focus of the out t.

Casual clothing doesn't need to stick to the blues and grays of business wear. Explore shirts,
jackets, and even trousers in rich colors like burgundy and forest green, or for a more muted
look pastels like pink and sea-foam green. They take even a basic chinos-and-collared-shirt look
and turn it into something unique.

#3 Layer

A complex life deserves a complex look. Don't be shy of visual clutter in your casual out ts.

Sports jackets over collared shirts are a good default out t, but hardly the sum of a
professional's options. Invest in turtlenecks, cardigans, long-sleeved T-shirts, vest, long
overcoats, and other pieces that add complexity to your upper body.

Texture also adds visual depth that gives a simple out t a little added gravitas. Visible weaves
are great in jackets and trousers, as are decorative elements in shoes and belts. You're wearing
it for fun, so have some fun shapes in there.

Casual Clothing For Professional

Men
1) A couple of patterned or textured sports jackets. Throw them on over any out t with a
collared shirt and long trousers for an instant upgrade.
 2) Pocket squares. You're old enough to be
paying attention to details, and you should have
one of these in the breast pocket any time you
wear a jacket.

3) Gray wool slacks. Think of them like you used

to think about blue jeans: default pants for
every situation, to be dressed up or down as
needed.

4) A good collection of casual long-sleeved

dress shirts and polo shirts.

5) Shoes that make a statement: brogues,

saddle shoes, chukka boots, or whatever other
interesting options catch your eye. Tennis
shoes and plain black/brown dress shoes should be reserved for playing tennis and business
meetings, not worn for fun.

6) A few neckties with an interesting color, pattern, texture, or shape (bow ties are an option
here). Wearing a tie every time you wear a color shirt is stodgy, but wearing a tie for fun once in
a while shows that you're in control of your look.

Business Dress for the Professional Man

Your business dress needs are partially going to be determined by what the “profession” in your
“Professional Man” is — lawyers need a wide selection of suits; car mechanics don't. Every man
can use at least one suit in the closet for interviews and business meetings; beyond that use
your judgment and focus on buying the kinds of clothes you wear to work regularly. But there
are a few rules that work at any level of formality:

#1 Be Realistic about Fit

Don't kid around with the t of your good business clothes. Get them tailored speci cally to
you, always, and be honest about the measurements. Counting on losing those ten pounds next
month is just kidding yourself. When you do lose the weight, you can have the clothes adjusted.

At the professional age the t of your clothes is a major sign of success (or failure). Someone in a
slumped suit, or a sports jacket that's too short for his arms, is someone who looks like he can't
afford or doesn't care to look better. Neither one is going to inspire much con dence in your
friends and peers.

You're better off owning less clothes that t better than a lot of clothes that t okay. Prioritize
getting everything in your business wardrobe looking sharp and feeling comfortable over
adding items to the closet.

#2 Exceed Standards and Set the Example

Think about the basic dress requirements for your job, whatever it may be.

Now plan on exceeding them.

In business, there's no reason to blend in. If you work for someone else — a boss or an employer
— it shows them that you're comfortable where you are and don't plan on advancing. If you're
self-employed, it shows clients and business partners that you're getting complacent.
So plan on upgrading a small step beyond the
“dress code” at your workplace, whether it's an
of cial set of rules or not. If khakis and an open-
collared dress shirt are the norm, alternate
casual jackets and neckties as ways of
exceeding standards. If everyone's already in
suits and ties, invest in good dress shirts and
neckties, and make sure you're always sporting
a pocket square.

#3 Complete the Ensemble

Wearing a good suit, or a good pair of slacks

with a nice blazer, is only half the battle. The
devil is in the details.

A professional man needs to strive for professionalism in all of his business clothes, not just the
big pieces.

Dress shirts should be of good quality and tted properly around the neck, with no loose collar
standing off the skin. Cuffs should be visible a half-inch or so beyond the end of the jacket
sleeve. Pocket squares should be present, bags should always be leather briefcases and not
cloth backpacks or messenger bags, and leather and metal accents should always match (no
silver watches if your blazer has brass buttons, etc.).

The difference between a man in a nice suit with no accents or sloppy details and a man in a nice
suit with all his smaller accents crisp and in place is a striking one. Once you're getting out of
your 20s, it's a difference you should be able to manage every day.

Business Clothing For Professional Men

1) A proper suit, preferably a made-to-measure or bespoke one. 100% wool, good t, dark color,
and a reasonably conservative style keeps it appropriate for all business occasions.

2) At least one pair of gray wool trousers. When your suit is too formal, wear these with a blazer
instead.

3) A navy blue blazer. You'll need one of these at pretty much all ages, in fact. Add more blazers
and sports jackets if you're at an of ce that doesn't require suits but does expect “business
casual” dress.

4) Lightly-patterned or textured sports jackets for business-casual events. Throw them on over
your dress shirt and slacks rather than stopping with just the collared shirt.

5) Lots of neckties, if you wear collared shirts to work on a regular basis. Nothing says “stuck in a
rut” like the same half-dozen ties over and over again.

6) A couple of plain white dress shirts, not button-down collar, for the most formal meetings and
occasions.

7) Plenty of lightly-colored or patterned dress shirts for more casual business wear.

8) Black leather balmoral oxfords, in good shape and well-polished. A similar pair in brown is
good for slightly less formal suit-and-tie occasions.
9) Good belts and a good wristwatch. If you're not wearing a watch at this age you look a little
careless.

The Mature Man: 45+

By the time you're in your 40s people expect you to take life pretty seriously. You're also getting
old enough to start seeing hints of ageism in how people treat you, especially if you're looking
for a new job (increasingly common as the economy ounders and bene ts are slashed).

Dressing in your mature years means nding a balance between dignity and stodginess.
Timeless styles are increasingly your friend; trend-based fashions that fade in and out less and
less so. It's also time to simplify a little, leaving the intricately detailed out ts to younger men
and opting for simple elegance whenever possible.

Casual Clothes for Mature Men

If you don't want to be taken for a xed-income pensioner, don't give up on your casual style.
Stretch pants and sweatshirts say “done with life.” Have a little more crispness than that as you
welcome your silver (or vanished) hairs.

#1 Outdress the Younger Men

One of the joys of old age is that you no longer look like you're trying too hard if you wear a suit
for fun, or are the only man in a crowd wearing a blazer. You're an old guy. You get to do things
like that.

Casual suits are one of the underused joys of American menswear. Have a few — in striped
seersucker, plaid wool, pastel linen, or anything else that strikes your fancy. When you're not in
the mood for a suit, go for slacks and a sports jacket instead. An open-collared dress shirt or a
turtleneck underneath will always say “I dress this way for fun.”

The key thing to avoid is anything that smacks of laziness rather than studied casualness. Your
out ts should look like they took a little thought and work. There are a lot of young men out
there eager to dismiss their elders as “tired-out” and “over the hill” (often so that they can feel
better about ignoring good advice)

#2 Wear All the Extras

It's surprising how many great pieces of clothing some men never bother to wear. Hats, gloves,
scarves, cuf inks — these are the re nements that an elder gentleman can use in his everyday
wardrobe.
A few beloved hats are something every man should own by the time he's 40. If you don't have
them yet, work on nding them. Colored leather gloves (anything from a sedate burgundy to a
stylish yellow) are a three-season piece that almost nobody thinks to wear anymore, setting you
rmly apart without being anything but the soul of dignity.

Smaller accents like French-cuff shirts with casual cuf inks, colored pocket squares, and neck
scarves all complete the image of a man with both the time and the skill to out-dress everyone,
even on his day off. The only touches worth avoiding are ones that evoke a speci c past era,
whether they've come back into style or not — younger men are wearing cravats again, for
example, but an elder gentleman wearing one is going to look like an oil painting from the 19th
century. Stick to timeless styles.

#3 Don't Be Afraid to Startle

The older you get the more people will want to pretend you're invisible.

Don't let them.

Wear the unusual, the interesting, and occasionally the downright startling when you're on your
own time. Got a favorite old tweed jacket? Pair it with a pair of brightly-colored cotton or linen
trousers to go from “aging British squire” to “urbane sophisticate.”

Mid-forties and up is also the age at which it nally becomes acceptable to wear novelty ties for
fun. Don't make a habit of it, but don't shy away from the occasional startling necktie either. It'll
put a smile on people's faces when they're looking at you, and that's always a good thing.

Just a sharp-looking pair of shoes can be enough to draw the eye in an otherwise-relaxed out t
like slacks and a knit shing sweater. Whatever it takes to remind people that you're there and,
if necessary, that you're older and wiser than them. Even what you carry in your pockets can
come in handy here; young people these days are always impressed when someone in their 60s
pulls out a smart phone and opens its web browser.

Casual Clothing For Mature Men

1) A few non-business suits. These can be casually patterned or made from traditionally casual
materials like linen and seersucker.

2) Vests and waistcoats are a great way to look dapper without wearing a jacket (they're also a
nice way to slim any expanding waistlines). Have a few in the closet, either as part of three-piece
suits or on their own.

3) Lots of wool slacks and sports jackets. The more colors, patterns, and textures you have in the
wardrobe, the more mix-and-match looks you can create.

4) Good, casual sweaters: cardigans, Guernsey or Aryan Island sweaters, etc. Nothing baggy or
shapeless.

5) Comfortable, well-shined leather shoes in a variety of patterns and colors. A few pairs of
dress boots wouldn't hurt either.

6) All the little elements: hats, gloves, walking sticks, scarves, etc.

7) A good knee-length trenchcoat or similar overcoat. More than one in varying colors is no bad
thing.

Business Clothes for Mature Men