How To Master Casual Style Without Feeling Underdressed

Have you ever walked into a room and felt like everyone was staring at you? Uncomfortable, isn't it?

I've found this always happens when the way I've dressed is noticeably out of place for the situation I'm in.

In some cases you want to stand out for all the right reasons -- like slightly overdressing at event that you'd want to get noticed at.

Other times, you can stand out like a sore thumb.

So how do you walk that fine line between getting noticed and standing out like a sore thumb?


First And Foremost, Always Keep It Age Appropriate

It's tempting to throw on an old pair of jeans with your favourite t-shirt and worn in sneakers.

I can see why. It's a comfortable and reliable look that's easy to fall back on.

This might be ok in your teens and early 20's but if being taken seriously matters to you, you may want to reconsider.

Casual Doesn't Mean Sloppy

I used to think that dressing casually goes hand-in-hand with looking sloppy or like you don't care.

What I've learned over the years is that this couldn't be further from the truth.

It's actually quite easy to dress casually and still feel like you're well put together.

At the end of the day it comes down to your mindset.

How you view yourself will determine how you carry yourself and ultimately how you present yourself.

For example: it's easy to feel lazy or unproductive when dressing casually. Doing so will result in a lazy and unproductive day.

Since I work for myself, there's no dress code. Wearing my Adidas tracksuit would be acceptable since there's nobody to answer to.

Here's the catch, if I did dress like that on a regular basis you'd be less likely to take style advice from me.

That approach (as comfortable as it is) would make you question my credibility since it wouldn't be practising what I preach.

Studies have also shown that how you dress has a direct impact on how well you perform that day.

It's almost as if the mind can't tell the difference between your "work self" and your "weekend self."

If you're working from home or have a flexible dress-code, you may want to keep this in mind.

Take The Smart Casual Approach

My personal favourite!

Taking this approach basically sets you up to be well-dressed for nearly every occasion.

You might be wondering, "What is smart casual style?"

Smart casual is all about versatility since it takes elements from a few different genres of menswear.

First and foremost, it's casual.

A staple piece when dressing smart casually is either a great pair of jeans or chinos.

Match these with a well-fitted button-up shirt, classic sneakers (or boots), and a great outerwear piece like a bomber jacket or topcoat and you're well on your way!


Smart casual style is also about incorporating elements of somewhat formal pieces into your outfits.

That's where items like Chelsea boots, button-up shirts, and knit sweaters come in handy.

The trick when taking this approach is to walk the fine line between dressing too casually and fully dressing up.

Your goal is to find that happy medium.

Doing so guarantees that you'll be prepared for nearly anything that comes up during the day.

If your days are anything like mine, there isn't usually enough time to run home and get changed for the countless commitments you've made.

My days move at a pretty fast pace between working on Street Gentlemen, meetings, and having somewhat of a social life.

This means that I need to be prepared for a variety of situations.

This also means that the way I dress needs to be professional and versatile.

I could easily dress formally from head to toe but there's always the slight chance of coming across as "too stuffy."

On the other hand, I could dress comfortably and casually.

Of course the risk here is that I likely won't be taken as seriously as I'd like to be in certain settings.

Based on my experience, your best bet is ALWAYS to walk that fine line between formal and casual.

Yes, there will be days when you lean more towards one side or the other.

If you take this approach the majority of the time your life will be much easier -- I promise!

Last Thoughts:

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