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Diversion: 5 Legit Reasons Why Dressing Well Helps You Succeed As A Man

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I’ve run men’s groups for a living for the last decade. I get to observe the private lives of a lot of men from all walks of life.  One of the topics that comes up over and over again is men’s fashion.

Most people expect to find a men’s group in discussion about more sensitive topics and we do cover those as well. But the reality is that fashion for men is about so much more than choosing clothing for the day. It means a lot more and influences us more than we care to admit.

Here is how I’ve seen fashion help men become more successful and happier in life:

#1 – Good fashion creates confidence

As men we’d all love to feel confident all the time. We will even go as far as faking confidence (cockiness) to give others the impression that we feel confident. Yet in our online men’s groups we see time and time again that every man struggles with confidence at times.

Confidence is something that wavers for everyone. Even some of the celebrities and pro athletes in our men’s groups have days where they just don’t feel that great about themselves, their lives or their place in the world. Same goes for women too.

And even though low confidence is human, some days it can hurt you as a man. Low confidence can lead to indecisiveness or emotional decision making. You can say something you may later regret. You may lose out on an opportunity that could fuel your growth and success.

The true way to build self-confidence for the long term is to change the story we tell ourselves about ourselves – change our internal narrative –and how we think in general. But there is a confidence hack that seems to work for all men: fashion.

Even on the lowest days, putting on a crisp new shirt or pants that fit well can give you that boost that you need to get through the day feeling good. I’ve seen it lift guys up from a 3/10 to a 6/10 in confidence on a low day which is enough for them to get out into the world and lead aa a man. It can often help a man just get through a tough day.

And if you did this day after day, imagine where your higher confidence would lead you. You’d make decisions coming from a better place. You’d likely be offered more opportunities. And you’d see more success and happiness as a result.

#2 – Poor fashion can destroy confidence

A lot of men don’t consider the other side of the fashion confidence coin.

Because poor fashion choices can lead to less positive interactions with others, making poor fashion choices can drastically affect a man’s confidence.

He can feel people shying away from him, women engaging with him less and a sense that life isn’t going his way. He may already feel a little lower and then if someone reacts negatively to him because of what he is wearing, that is likely to make things worse.

So make sure you’re not hindering your confidence by dressing like a slob

#3 – First impressions are everything in business

Business is based on trust. People don’t trust people that look slobby. It sounds harsh but it’s true.

We’ve seen lots of guys in our men’s groups hit slumps in their respective careers and one of the things that always helped get them out of it was looking sharper. Fashion got the deal they needed to turn things around.

People default judge men who are dressed well as more successful, better leaders and more trustworthy to do business with.

Any type of agent knows this well. Real-estate agents, brokers, bankers, hotels; these industries have tested out their workers’ attire over the last century and have found that dressing sharp leads to more business.

So if you want to make a good first impression and have people trust you – and you should – then make sure you invest in your fashion.

#4 – Good fashion starts conversations

People like to make comments when others are dressed well. I can’t count the number of times that I was wearing well-fitting clothes or a unique fashion piece and had someone say “Nice hat”, or “that’s a cool dress shirt”.

Not only does this help confidence (see above), it also gets you into conversations that you wouldn’t have ended up in otherwise.

This is beneficial for two reasons:

  1. Compliments on your clothes feels good. It’s a normal thing to feel good with a compliment. This makes life more enjoyable and fun day-to-day.
  2. Opportunities only come from people. Success doesn’t happen in a vacuum. Ideas, introductions and opening doors always come from relationships. So if you want to advance your growth and success you want to be talking to more people. Fashion will help.

So go find some clothes that fit well. Hunt for a few unique pieces that will make it easy for people to start conversations with you.

#5 – Good Fashion Draws Your Kinds Of People In

The fun part about fashion for a guy is that it isn’t just about looking good, fashion is an incredible to show the world who you are and what you’re into.

An example from my own life. I love to surf and kiteboard. So I find clothing that fits well and looks unique but still has either branding or imagery about surfing or kiteboarding. This could just a really unique pair of flip flops, well-fitting skinny jeans from a surf brand or a vintage hoodie from a thrift shop in a surf town.

When I wear this stuff and I’m out and about, it’s incredible how many people ask me if I surf. I’ve had friendships develop from these conversations that have lasted for 10+ years!

Maybe you’re into football, MMA, videogames or philosophy. It doesn’t matter!

I have a friend that is deeply into philosophy and he’s been able to find really cool clothing that makes him look and feel like more of a philosopher. He even got high-quality, slim-fit t-shirts printed with quotes from his favorite philosophers. No matter where he goes he has people who also study philosophy for fun approach him and say “cool shirt” or “isn’t that quote from Marcus Aurelius?”.

This is an easy way to attract people to you and build relationships with people that share your interests.

It Doesn’t Have To Be Complicated Or Expensive

And your clothing doesn’t have to be complex, pricey or fancy.

It’s as simple as finding quality clothing that fits well for your frame. You just need to keep trying stuff on from different brands until you find items that fit you really well.

Even something as simple as a well-fitted white v-neck t shirt and a dark pair of jeans with the right tapering can do the trick.

We hope our observations from the guys in our men’s groups help convince you to invest into your fashion and ultimately help you become happier and more successful.

Author Info:

Sean Galla, founder Men’s Group

Sean has been running men’s groups for 10+ yrs for men from all walks of life, including pro athletes, celebrities and successful entrepreneurs. He now facilitates online men’s groups over at

Sean Galla

Sean Galla