1. Practice

You have to make dressing sharp a habit.

It’s not something that you just do once in a while and think you’re going to fall right into it.

Habits are effortless because we no longer have to think about it. Think about brushing your teeth. It’s a habit you don’t think about unless you’re put in a position which you can’t do it.

So you also set things up and I talk about this in the Interchangeable Wardrobe.

I help men develop this in my Style System. We develop systems so that dressing sharp is easier than not dressing sharp. All the clothing I brought, I brought a small suitcase, everything was interchangeable and everything was about me putting my best foot forward.

You don’t go out there and try to pull off clothing that you haven’t worn that you feel uncomfortable in. What you’re actually wearing, you’ve worn before and you feel good in.

2. Fit

So well-fitted clothing actually is very, very comfortable.

Poorly-fitted clothing, not only does it look bad, but if it doesn’t even fit the wearer’s environment and his personal style, it’s restrictive as well.

Clothing that is way too big on you, you’re not going to have so much movement. High armholes, fitting you well in the crotch area, all of that actually gives you more movement.

That’s why jeans are actually so enjoyable to wear. Think about how jeans or a well-fitted pair of denim fits you in the crotch area. It’s probably a bit tighter than your pair of dress slacks, which you may have bought off the rack.

And because there are so much room there, because the crotch hangs so low, you can barely move your legs if you think about it, so well-fitted clothing is very comfortable.

3. Environment & Occasion

I’m a custom clothier.

There was an expectation after I started talking with people for a while, if I turn up in a t-shirt and jeans, even though if it was a very expensive t-shirt and jeans, that would not connect with who I was and the occasion I was there for.

I would have had a disconnect between what people imagined a custom clothier and style guy is versus who I was presenting.

So for me, it was important that I did wear a sports jacket, a nice dress shirt, and I oftentimes wear my raw denim with western boots, although I did wear a grey flannel trousers along with a pair of monk straps, but dressing sharp, guys, does not mean that you have to wear a suit.

4. Compliments

During the conference, I received about ten compliments a day on how I looked, most of them from women and it felt really good.

And I spoke with Matthew Kimberley, the guy I’ve been talking with before who I met for the first time, a well dressed Brit and an excellent sales coach. He had received about the same and we talked about it.

It was just interesting the way people would react to you when you’re really well dressed.

Compliments feel good, gentlemen, and when you receive compliments, you start to give them out more freely.

You just feel better. You’re on this high. I can tell you that I had a great conversation with the PR manager of Military.com because when I saw her, I didn’t know her. I mean, she was a very attractive woman, but I noticed her shoes.

She had this snakeskin. They weren’t real snakeskin, but they looked like these snakeskin shoes, and I was like, wow!

Those are some amazing shoes. And instantly, we got into a conversation.

It wasn’t the typical, “What do you do?” It was a fun conversation, a bit playful.

The next thing I know, I find out she’s the PR manager for the Military.com and we’re talking about another idea that I’m working on the side to help military vets better transition out, so it was a great conversation.

I got into it because I complimented her. I made her feel great.

By the way, Matthew Kimberley’s book is called “How to Get a Grip“. It’s right on Amazon. I advise that you check it out. He’s an excellent sales coach, so if you’re a business guy, check it out.

5. Confidence

Confidence comes from a number of things.

It is something that we can gain and lose within a matter of seconds and minutes, and all of that what I had just talked about helped build up my confidence while I was there.

When other people project a positive feeling, you can’t help but radiate confidence.

I’ve got to share this with you guys. Pat Flynn during his presentation, he pointed me out and he thanked me for a video I had sent him on how to improve his style a couple of years ago.

And I can tell you that him thanking me, giving me that great compliment in front of all those people, it just made me feel so great. I felt like I was radiating because it was two years later to get recognized for putting in some effort.

And to see him up there as an amazing blogger who writes over at Smart Passive Income, his style transformed based off of something I was able to give him, I couldn’t help but walk a little bit taller throughout the rest of the conference.

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