3 Critical Mistakes Men Make When Dressing Casually… and How to Fix Them

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7 seconds. That’s all we get…

We only have one shot at making a first impression. Our window to take advantage of it is microscopic.

How would you like to guarantee that you’ll make a great first impression no matter what situation you’re in?

Before we get to that let’s talk about a gentleman I coached a number of months ago.

Troy is a successful salesman at a local utility company and has managed to build himself a notable career in the short time he’s been there.

He works with large accounts worth hundreds of thousands of dollars and enjoys his work.

When at the office he would always dress professionally in a pair of dress pants, dress shoes, and one of many button-up shirts.

Here’s where things get interesting…

On the weekends Troy would ditch the office wear for something much more casual — jeans, t-shirts, and ball caps.

Pretty standard for a lot of guys.

The problem with his approach was that it was TOO CASUAL.

Since he’s built like a linebacker he also had trouble with finding clothes that FIT PROPERLY (check out this article to learn more about fit).

Also, the chances of seeing a client or coworker while running errands is high.

The last thing Troy wanted to do was give them the impression that who he is at the office isn’t the real him.

In other words he didn’t want to mislead his colleagues.

Troy’s not alone. When ditching the office-wear for something more laid-back a lot of guys miss the mark.

The reason is simple — there isn’t any CLEARCUT guidelines for what defines casual attire.

On top of that, it seems like there’s endless clothing options available and trends keep changing from one season to another.

How’s a guy supposed to keep up?!

No need to worry. If you’re reading this you’re in the right place.

Today I’m going to share with you a few solutions to avoid the common mistakes men make.

The same tips that transformed Troy!

You’ll also be introduced to what many men’s style experts are referring to as the ‘Smart Casual’ look.

Smart Casual is basically the middle ground between wearing jeans & a t-shirt or a full suit & tie.

Here’s 3 Common Mistakes Men Make…

  1. Holding on for sentimental value:

It may not seem obvious but this one’s a very common mistake.

It could be a favourite sweater from college or a souvenir t-shirt that you picked up while on vacation.

Those memories are great but let’s save the souvenirs for the photo albums.

SOLUTION: Some of the staples every man should have in his wardrobe would actually solve this problem for you.

A grey crewneck sweater will easily take the place of any old college gear. It’s comfy and versatile since you can easily dress it up or down.

The Smart Casual approach would be to wear a white button-up shirt underneath with the collar sticking out.

   2. Sticking to what they know/playing it safe:

I’ve seen this one far too often with the men that I’ve coached. Let’s be honest, you can only own so many blue shirts.

Playing it safe works because it’s easy to stay in a comfort zone.

I get it, taking risks can be scary. Who knows how people react when you branch out.

Don’t worry about whether you get it right or not.

More often than not people are willing to acknowledge the courage it takes to break from the norm.

Solution: Take a look in your closet. Does a lot of your stuff look similar?

In other words, do you have variations of the same shirt in different patterns or slightly different shades?

If this sounds familiar I encourage you to branch out. In this case the grass is greener on the other side.

I can’t count the number of conversations I’ve started with complete strangers that turned into friends or acquaintances because they commented on something unique I was wearing.

The Smart Casual approach would be to take a small risk in the form of a subtle details.

Venture out into a pair of attention grabbing socks.

Though it may not sound like a big change, consider it a small victory. This is a great way to showcase your personality without being too loud.

   3. Jumping on trends just because everyone else is:

First of all, trends ALWAYS come to an end.

So to invest heavily in what’s trending can be risky since you’ll have to update your wardrobe in about a year.

Now, picture yourself passing someone you know on the street but not having the time to talk.

What 3–5 things about yourself would you like to communicate to them in those few seconds?

A great example of those qualities could be that you’re confident, successful, and happy.

Taking the time to define what message you want to send through your style can eliminate a lot of confusion and reduce frustration when shopping.

Solution: What’s commonly known as Timeless Style will be your best bet. Considered a way of dressing that’s always relevant.

Think dark blue jeans, white t-shirts, aviator or wayfarer sunglasses, white sneakers, and leather jackets to name a few.

These items were in style as far back as the 50’s.

Invest in Timeless pieces and you’ll be guaranteed to look great no matter what’s currently trending.

This will save you money in the long run since you won’t have to upgrade your wardrobe as frequently.

This doesn’t mean that you shouldn’t buy trendy pieces.

Just do so in smaller doses rather than diving in head first.

Final Word:

At the end of the day your style is something very personal.

No two guys will ever be the same. I encourage you to venture out of your comfort zone.

Troy did and ended up winning the ‘Best Dressed Male’ at work.

He was in good company…the best dressed female was the boss’ wife.

Troy proudly displays his Best Dressed Male award he received at work after style coaching

I’d love to hear your thoughts or if you have any questions please get a hold of me here: Sunjeev@StreetGentlemen.com

Finally, I’ll leave you with my favourite quote…

“If you look good, you feel good. If you feel good, you play good. And if you play good, they pay good.” Deion Sanders

Take care, Sunjeev (a.k.a Jeevs)

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