obstacles for better style

The Three Obstacles Stopping You From Looking Great

If you haven’t noticed yet, I’ve been conducting some “experiments” on you guys.

I’ve actually been conducting a few surveys. 

These help me thoroughly understand what you’re looking to learn, what challenges you’re having and basically, how I can help you improve faster.

I’ve also been digging deep into surveys Nicolas and his team conducted when he owned it. And I’ve been talking to a lot of you personally, getting a great understanding of how I can help you better.

(As you can tell, I’ve barely slept)

Today I’d like to discuss a few of the recurring themes I’ve discovered.

Obstacle #1: Colors

Here’s an experiment of your own I’d like you to try.

This weekend, head out to a shopping mall. Look around at all the guys. Then come back and tell me how many different colors you see people wearing.

My guess?

It won’t be much.

In general you’re going to see guys wearing gray, black or charcoal.

Not bad colors by themselves (except black which I don’t recommend often as it fades too fast). In fact gray is one of the four basic colors we recommend for beginners.

Disclaimer: I’m wearing black right now! However, I’m working. In my basement. By myself.

But if that’s ALL you’re wearing, it’s time to spice things up a bit.

No, you don’t have to go out and buy a rainbow-color shirt. (Please don’t). 

However what you can do, even if you’re a little hesitant on adding more colors to your wardrobe, is stick with basic colors as part of your main outfit, while brightening it up with splashes of color.

Here are a few examples…

Instead of khaki Chinos, try blue or red…

Add a little white to your business shirt…

White collar blue business shirt

Or wear a classic jeans/blazer combo with a splash of color like the guys from Marquis of fashion did…Color-outfit-for-men

As you can see these outfits are easy, stylish and easy for pretty much anybody to pull off.

Think of all the various places you can add a little color. Your collars. Your cuffs. Your pants. Your shirt. Your accessories. 

For the summer, chinos come in all different colors you can try out. Rust-colored chinos, marine blue, sometimes even green, etc.

Even if you don’t think you can pull it off, TRY. You might be surprised. And start small.

And when you’ve added a little color to your wardrobe, next up is…

Obstacle #2: Materials & Texture

Material can be a little more complex than color.

Mostly due to cost.

Basically, you have to completely replace your basics with high-end, elaborate materials. It’s easy to understand that cashmere is much nicer than a blend of wool and synthetic fibers. 

Problem is, good materials are very expensive!

If you’re on a budget (I know many of you are), you can add different materials to your wardrobe in steps. You can also start small.

For example, you can try a nice, lightweight cashmere sweater…


Or if you’re a bit more bold and want to really liven things up, you can add multiple layers of fabric to really grab attention…

Screen Shot 2014-07-10 at 8.24.37 AM

Another great look appropriate for summer is something like this Allsaints Massachussetts shirt, easy to match with a pair of slim-fitted jeans and loafers.

massachusetts short sleeved shirt

Here’s what I want you to notice.

All the things I’ve just shown you are still relatively simple and easy colors – it’s the material that does all the work.

Going beyond basics for elaborate materials requires a good wallet, but it’s worth the effort. Your entire wardrobe doesn’t need to be filled with high-end clothes. Just splurge when you can, and flaunt it.

Which leads us to our final obstacle…

Obstacle #3: Your Own Mind

This last one has nothing to do with clothes. It has nothing to do with your budget.

It has everything to do with YOU.

When you are first beginning to dress better, you WILL encounter resistant from your friends, family, co-workers, etc. Most guys get stuck because somebody pokes fun at them, saying they’re “too preppy”, or making country club jokes.

Let them pass.

A subscriber emailed me a few days ago saying he was having a hard time really grasping his style because every time he dressed like he wanted, his friends would ask him if he was going to a yacht party.

Please understand: This is nothing more than jealousy.

When other guys see you dressing better than they are, they are going to get defensive. They know (even subconsciously) that you’re the one who’s going to be getting attention, not them.

So they unconsciously try to stop you from doing so.

It’s the same if you lose weight. As soon as you get to a healthy weight, all of a sudden you’re “too skinny”. If you’ve ever had to lose 20+ pounds, you’ve probably received those comments.

It’s hard to deal with, but it’s worth it.

One of the FIRST things we cover in the Kinowear Bible is getting past those mental blocks and understanding why you are upgrading your style. Getting past those initial barriers takes a little work. That’s why I always recommend starting slow and working your way up.

Here’s what typically happens.

Stage 1: You wear something really nice for the first time. Girls say something like “Wow, you clean up nice!”. Guys say something like “Dude, why are you dressed up?”

Stage 2: You begin to gain more confidence and start getting compliments more often. You’ll probably notice that when you go somewhere where people don’t know you, you’ll start getting looks (good ones). If you have a girlfriend/spouse, they’ll already be used to your new style and compliment you on it. Your friends will still make jokes, but less often. Usually when you’re trying something new.

Stage 3: After a few months, people will forget how you used to dress. You will now be the guy who dresses sharp. Period.

You HAVE to get past the initial awkward stage. It’s going to happen. What’s important to know is the the closer you get to the style you feel most confident in, the less you’ll get comments that bother you. You might love the styles of the images on this blog post, or you might hate them. That doesn’t matter. You have to begin looking at pictures for the IDEAS, not the specific outfit itself.

One thing I’m going to try and do more of is add more styles that the average guy can wear. A lot of you have commented that the styles shown were a little too high-end for you. I hear you!

What’s Your Experience?

Which of those 3 stages are you at in your life? I get comments from people in all different stages. Upgrading your style is one of the best things you can do for yourself but it does bring some unique challenges (comments from others, budget, etc.).

It’s all about pushing yourself out of your comfort zone and trying new things.

So let me know in the comments how you’re dealing with that!

  • ferdic

    HI Jeremy, great article! I really appreciate the effort you put into the website… (y)

  • dnm

    hey, great post. here’s my experience. I started to dress better about 8 months ago. I had lost a significant amount of weight and I needed new clothes. I was about to stay on the same lack of style, when having a new shirt made me feel like I was the best dressed man on earth. then I would wear that same shirt about 500 more times, then buy another new one and repeat. jeans and some pair of shoes, the same one day in day out until it got wholes in it. (you know that feeling, when you shop for shoes and, in the shoe store you look at the shoes you were wearing and you can’t believe how bad they are? now, I don’t know it either anymore…) so, a couple of months into this (new clothes in smaller size but still dressing like a slob really) I had to buy a suit.

    I really hated the idea, because I knew I wasn’t going to wear it more than 2-3 times per year, if that, but there was a meeting I had to attend and there was a “gala dinner” which absolutely required a suit, and I was literally swimming in my old one. So, reluctantly I take my wife to the mall to help me buy the damned suit. we go into Massimo Dutti and the sales clerk is really good and is immediately able to spot my size. I put the suit on and when I looked in the mirror, that’s when it all started. I basically saw myself 20 years younger. with losing weight, I was starting to look good. I forgot I could look good, really. I used to be a good looking guy, swimming team, played water-polo and all that and I had all the confidence in the world, so getting fat didn’t really get to me in terms of confidence, behavior around women and all that.

    I actually started to lose weight because of health reasons, wanted to avoid type 2 diabetes, not because I wanted to look better. anyway, back to the story about dressing – I wore that suit every day at this three days meeting. It felt so good, I didn’t want to take it off. When I got home, i took my family out for lunch and wore the suit. Then I started searching the net for clothes and masculine style. I learned a lot.

    I still don’t have another suit than that first one (navy worsted) because my workplace is not the suit wearing type; even though I could get away with it as I am management, I prefer not to, because I learned also about having some sense of the occasion. But I am wearing tailored jackets and pants every day. no more frayed jeans; I have 16 pairs of shoes, more than my wife actually… maybe this is getting a little crazy.

    How did I get away with it? quite easy. the guys at work are either my reports or my peers; higher management is suited up anyway. From the guys I got several disoriented comments, along the lines of “why the hell are you all dressed up” which I ignored; when the comments could have been taken as compliments I said a simple “thank you” and that was it. now the guys are keeping their mouths shut, and I think I notice some of them trying to step up their clothing game as well. the women, they have been amazing. I haven’t got a single nasty word, or look. I notice lots of surprised, in a good way looks, and the more daring ones are saying something, always nice.

    The thing that got the most attention was the pocket square. the first day I wore one (which was actually the jacket’s pocket lining turned out) I had 4 women in the office mention it, and in a very positive way. I am still amazed on the effect a piece of cloth like that can have on women. now I wear one almost every day.

    but the biggest compliment came from my wife. before I started to dress up she was in pretty much the same situation – had lost a lot of weight, more than me actually and started to look really good, but for some reason was still behind in clothing. she was dressing up only when having to attend some very formal business occasions.

    So, I kept dressing up while she was in jeans frayed at the cuff and sneakers… until some day when we were going out for lunch, I came downstairs wearing jacket and pants, nice shirt and shoes, etc. she was in her usual uniform, but this time she said, wait for me in the car. so I go to the car and 10 minutes later she comes wearing a fantastic dress I had never even seen before. she gets into the car and says “well, I had to keep up with you”. since then we both enjoy dressing well and going out together has stepped up to another level. sorry for the long comment, but you asked for it 😉

    so yeah, go for it, take most of the comments as compliments, say thank you, ignore the snarky ones and move on, is my advice.

  • Thanks Ferdic I appreciate that!

  • WOW. Thanks for taking the time to write out your story! Seems you went through the 3 phases pretty much exactly to the “T”.

  • Javier Morales

    So Jeremy, do you recommend dressing up for an early college student? I already dress well, but never slacks and tie and expensive shoe well. I typically go for the colorful pants and shorts and shirts during the spring and summer, and for the sweater and button down and earth tone pants during fall and winter. As for shoes, I pull off the boat shoes and desert boots. Is there anything I should be adding as a second-year in college?

  • Javier, that depends on your goals. While you’re in class I think it’s completely fine to be more casual/dressed down. Then you can dress up a little more as you begin to talk with people about jobs, meet with your professors (they’ll subconsciously give you more respect/guidance), etc.