How To Dress Your Age (And Send the Right Message)

April 06, 2017

How To Dress Your Age (And Send the Right Message)

You’re at the bank…

asking for a loan to help launch your business…

“But you’re just a kid!” – They say

You’re 32…


If only people could look past your outfit to determine your age…


…there are ways you can make that happen.

Here are 5 rules about dressing your age so you can:

  • Look younger (but not “too young”)
  • Look more mature (but not “old old”)

Read the article to discover what they are.

Dress Your Age: Tip #1 – Ask “How Do I See Myself?”

Simple question, right?

But the answer isn’t that clear-cut.

You have to figure out the kind of image you want for yourself in photos, videos, or even when you stare at yourself in the mirror.

It’s about acknowledging your age – as well as the potential setbacks it can cause.

Are you an older guy who sees himself:

  • Switching to a career surrounded by younger men (like those in the tech industry)?
  • Reaching out to a crowd of youngsters while talking as a guest speaker?
  • Trying to get younger women interested in dating you?

Are you a younger guy who sees himself:

  • Asking for bank loans or investments from older men who put faith in your business venture?
  • Showing people your track record of success in your profession?
  • Earning the same kind of respect as mature-looking men (with a little more disposable income) naturally get?

By getting a good grasp of who you are, and those age-related setbacks to combat – you can align your style goals accordingly. And that will only make your clothing decisions much easier.

Dress Your Age: Tip #2 – Ask “What Message Do I Want To Send?”

What’s the best way to portray yourself – so others will want to help you achieve your goals?

Let’s say you’re an older guy who recently left the corporate world – and is now auditioning for films in Hollywood. Would you enjoy being limited to “dad” or “grandpa” supporting roles?

What if you want a Tom Cruise type of lead? You can show the casting directors your potential by dying your hair and sporting a leather jacket.

On the other hand… what if you’re a 20-something guy who’s starting his own company?

If you want a bank loan – you’ll have to convince that 40-year old officer that you’re not some naïve college grad with a huge ego. And if you want older men as investors, they’ll need to see beyond your age.

Those are the people who need to believe you’ve got what it takes to succeed. So it helps to put on a charcoal gray suit before meeting them for the first time.

Accessories are also great for adding character to your image:

  • Pocket Squares – choosing a bright-colored pocket square (to go with your jacket) can show you’re youthful, adventurous and less conservative or traditional
  • Bracelets – wearing a bracelet or two gives you a younger, edgier look (you can also combine a thin bracelet with a watch to stand out even more)
  • Watches – a quality watch will make you look high-status, respectable and mature

Dress Your Age: Tip #3 – Be Aware Of Society’s Expectations

Unfortunately, our world is a judgmental one.

Once you drive your first car – society begins to see you as less of a kid and a more of an adult.

You can dress with a little more freedom and yet, people will still pigeonhole you based on age.

The freedom to choose what to wear suddenly turns into “choosing from clothes you’re expected to wear” – so there are limitations imposed.

And since we all need to feel like we belong in our community – it makes sense to base our wardrobe options on these expectations for different age groups.

 Younger Man (20s)

  • Individuality – These are the years when you’re expected to be yourself
  • Rebelliousness – Try breaking some “rules” in fashion (you’re encouraged to stand out)
  • Experimentation – Imitate different trends or celebrity styles and see what works for you
  • Fitness – Take advantage of your youth by being active and wearing well-fitted clothes
  • Self-Control – You’re still expected to maintain some level of normality (as in dress appropriately for work, avoid ripped jeans, etc.) so you can be taken seriously

 Professional Man (Between Ages 30 and 50)

  • Self-Awareness – You care more about the kind of image you present every day
  • Responsibility – You show that you’re level-headed in terms of building your life, which matters when you’re applying for a loan or finding a potential spouse
  • Newfound Maturity – People assume you’ve settled down and transitioned into the next stage of adulthood (leaving behind old traits like tousled hair, unbuttoned shirts, etc.)

 Mature Man (50s and Beyond)

  • Sophistication – What you wear in public depends on where you’re going (like wearing high-standard attire to fine-dining restaurants, theater or symphony performances)
  • Wealth – While most younger guys would look overdressed in suits at nightclubs or rock concerts, you’re seen as someone like a VIP guest or the owner of the place
  • Leadership – You’re viewed as a leader, a man of wisdom or mentor for the younger generation

Dress Your Age: Tip #4 – Work With Different “Stereotyped” Pieces

The concept here is another form of role-playing, something the stars of Hollywood do best.

For example: If a guy plays a doctor on TV, what does he wear to look convincing?

Of course – there’s a white jacket or stethoscope around his neck. Those make up the singular image of doctors that society is so used to seeing.

Nearly every clothing piece that exists today has some sort of age-related stereotype (tied with specific personality traits).

So your job is to determine which items will help you play your intended role most accurately.

Younger Man (20s)

Associated personality traits: active, rebellious, adventurous

  • Bright colors
  • Sportswear/sporty gear
  • Leather jackets
  • Slim-fit jeans
  • Single-breasted, two-button suits (navy or charcoal gray) for guys who are fresh out of college or launching a startup

Professional Man (Between Ages 30 and 50)

Associated personality traits: self-aware, responsible

  • Colors such as pastel, pink or light green
  • Wool overcoats that reach up to the back of the thighs (dark navy, charcoal gray or khaki)
  • Dark-colored suits (made-to-measure or bespoke) which are reasonably conservative for business/formal occasions
  • Light-patterned or textured sports jackets
  • Navy blazers (can be worn with interesting styles of shirts/trousers for a funkier look)
  • Neckties with interesting colors or patterns (bowties are also an option)
  • Stylish shoes (brogues, Chukkas or eye-catching shoes that make a huge statement)
  • Plain brown/black dress shoes for work

Mature Man (50s and Beyond)

Associated personality traits: sophisticated, wise

  • Dark-colored classic suits
  • Light plaid suits (for social wear)
  • Dark-colored blazers
  • White or pastel dress shirts
  • Open collars without neckties (unless you’re in a formal environment)
  • Non-baggy casual sweaters (like cardigans, Aryan Island, Guernsey)
  • Sleek black leather boots (like Derbys)
  • Guayaberas (instead of polos)
  • Fedoras or Panama straw hats (during the daytime)

Dress Your Age: Tip #5 – Consult Those Who Matter To You

Do consider the opinions of the people closest to you. They’re the ones who can be brutally honest if you try on something that doesn’t work.

They can be your wife or girlfriend, colleagues, friends you see on the weekends, or even your parents (your father could definitely talk about dressing more mature).

Those people will make suggestions worth following – not just because they care about you. Let’s remember to some extent, we’re all judged by the people we surround ourselves with.

And that’s going to be the case for your wife. If she asks you to tone down the “younger” wardrobe – it’s probably because she feels pressured to dress similarly… and feels uncomfortable about it.

So side with your wife when it comes to this issue (as long as she’s not re-dressing you completely). There’s still a way for you to compromise while still projecting that younger-looking image.

 At the end of the day, always bear in mind these philosophies on dressing your age:

  • Have fun – it’s okay if your outfit doesn’t hit the bull’s eye at first (it’s part of the process)
  • Love yourself – stay true to yourself and use clothing to represent the best version of YOU
  • Be confident – feel as youthful/mature as you look and don’t let the clothes wear you



Also in Dress Well Today

How to Fold a Pocket Square / The Scallop Fold
How to Fold a Pocket Square / The Scallop Fold

April 03, 2017

“Big things come in small packages.”

If there’s one aspect of life where those words speak the truth…

…it’s your clothing.

Small details can totally transform your fancy jacket, whether it’s a suit, blazer or sports jacket

Especially the pocket square.

That’s right – this accessory does wonders for your wardrobe.

It’s a small but powerful way of showing:

  • Your keen eye for details
  • Your classy, sophisticated side
  • A style that commands attention

That’s why it’s important to know different ways to fold a pocket square (aside from the common types)…

…like the Scallop fold.  This article will help you master this quick, easy, and stylish fold in no time.

View full article →

4 Reasons You Need an Emergency Suit on Hand
4 Reasons You Need an Emergency Suit on Hand

March 03, 2017

4 Reasons You Need an Emergency Suit on Hand

As a businessman, you never know when you’ll find yourself unprepared or underdressed for an engagement — business meeting, luncheon, after-work drinks, et cetera — and when you may fall victim to a wardrobe malfunction. It’s vital to have a backup suit available when such a situation arises.

Four reasons my clients have found they needed an emergency suit (and why they now have one on hand in their offices) are:

View full article →

7 Ways to Dress up a T-Shirt
7 Ways to Dress up a T-Shirt

March 01, 2017

Ever heard a guy say this?

"Yeah, I'm not stylish - I'm just a T-shirt and jeans type of guy".


I love t-shirts...

They're a classic piece for a man's wardrobe.

I would argue that t-shirts are incredibly stylish.

So how are t-shirts stylish?

It all comes down to a few key elements to look for.

The mantra that you must wear a suit & tie every day to have style is a myth.

Keep reading for ways you can dress up a T-shirt & look AWESOME.

View full article →