How To Dress Like A Boss

I have a special treat for you guys today. It’s a sample lesson of my course, Level Up Your Dating.


The Lesson

Working on my looks was one of the best things I’ve ever accomplished. Not only does it make me feel great whenever I glance in the mirror, it also has long term confidence boosting effects that constantly amaze me.

For instance, when I put on 20lbs of muscle a few years ago, I felt like a goddamn ripped gladiator. I would look in the mirror, and see a badass looking back at me. My confidence went through the roof.

Since then, I’ve lost some mass, and now have a more average appearance, yet the confidence I acquired remains. Even though I recently  injured my shoulder, and developed a bit of a gut from not working out, I still feel great.

Hell, I even learned to love my belly, much to the chagrin of my coworkers and friends.

So, looks are important. The bad news is, you can’t change some main features of your face, like your cheekbones or nose, without going deep into something like surgery.

The good news is, you really don’t need to.

As men, we’re lucky that women are much less shallow than we are. Most of the time, they’ll take a well-dressed, well-groomed geek that takes care of himself over a smelly, unkempt, naturally handsome man.

In other words, the average geek that dresses well, smells nice, cuts his fingernails, and takes care of his appearance will beat out the Adonis who doesn’t make any effort.

Note: the Brad Pitt lookalike who does take care of his appearance will always have an edge over us geeks, and that’s ok. You guys have the rest of this blog to tip the scales in your favor. If the super handsome dude reads this blog too? We’re fucked.

The Instructions

In this mission, we’ll focus on your clothing.

As geeks, and men, you and I are not necessarily used to dressing like a boss. But it’s important that we do. Why?

In the real world, your appearance is the first line of contact with other people. It’s like your character in World of Warcraft, or your customization in Tekken, or which outfit you choose in Marvel vs Capcom.

If you dress like shit, even if you’re a great person, people will automatically assume you are what your clothes say you are. You can spend 20 minutes changing their minds, if they stick around, or you can make a small change and save yourself the hassle.

Think about it: why handicap yourself? Why not give yourself a headstart? They’re going to meet the real you once you start talking, why not make it sooner rather than later?

Plus, the confidence thing I mentioned earlier.

The bottom line is, being well-dressed sets the stage for them to accept your personality better.

“How do I dress better?” you ask.

“Like this,” I reply.

5 Simple Rules to Dress Like a Boss

1. Make sure your clothes fit
With your shirt or t-shirt, try not to wear something that’s too baggy or too tight. If it’s too baggy, you’ll look like you’re swimming in it, and if it’s too tight, your nipples will be staring at everyone.

Rather, wear something that’s close to your body type. The same applies to your pants or jeans. Make sure your waist size is right, and you can only fit one leg into each pant leg. As for the length, it should reach your shoes with a slight puddle, or no puddle. If your feet are swimming in your jeans, you need to get them shortened.

2. Wear colors that match
If you have no idea if clothes match or not, you need to familiarize yourself with the color wheel. If you’ve never seen one, run a quick google search: it may save you from looking like a christmas elf.

Here’s a great video primer to get you going:

3. Choose only ONE interesting item.
Being a super geek, I love to wear cool gear: purple shoes, a Shoryuken t-shirt, a Transformers hat, the list goes on.

However, for balance, and to avoid looking like a nutjob, I only use ONE of these items at any given time. When it’s day time, and I’m going to work or hanging with friends, I’ll stick with a cool t-shirt or sweater.

When I go out at night, I wear simple, two color clothing, and rock some badass shoes. Invariably, the ladies’ attention is drawn to them as my interesting item, and I always get compliments on my foot gear.

4. Match shoes and belt
Black shoes? Black belt. Brown shoes? Brown belt. And if you’re wearing funky purple or green shoes (as I am wont to do), the color of the belt doesn’t matter.

5. Fanny pack, cell phone holsters
No. Never. Don’t do it.

Exceptions: Are you an old man? Are you happily married and convinced your wife would never leave you for any reason ever EVER? Are you a multi-billionaire? Then by all means, go for it, but keep in mind that I still don’t condone your behavior.

The Mission

Alright, now you know the rules. Here’s how you’re going to put it all together: you’re not.

Instead, you’re going to choose your budget, and go to a trendy store nearby that has the look you’re interested in which you can afford.

You’re going to walk into that store, find the nearest employee, and ask him or her to make you an outfit.

If you’re nervous about what to say, try something like this: “hi there. I need some help picking out a cool outfit for a party in a week. Can you help me put together something? Like, a well-fitting pair of pants and shirt, with an accessory or a blazer or something?”

If you give them free reign to do what they want, I think you’ll make their day: everyone loves a makeover.

Space Invaders

Alright gang, that’s my chapter on dressing well. The version included in my book is a bit longer and more comprehensive, so go check out Level Up Your Dating and fix your love life.

5 comments add yours

  1. So far so good! People have been leaving me comments on twitter and facebook for this bad boy, and I’ve even received a couple of emails. Keep em coming gang!

  2. This is definitely a chapter that most geeks I know need to read. I know I have trouble with the color matching issue sometimes too, and I get strange looks…

    • LOL, don’t we all? I used to wear crazy stuff like an orange sweater, blue jeans, green shoes, gray scarf. Ended up looking like a circus clown half the time.

  3. Great chapter! And you men really are lucky we women aren’t as shallow. It’s your attitude, personality, hygiene (extremely important), your choice of clothing and how you carry yourself that really turns us on. And that is all in your (men’s) control. But you, Rami, already know this, that’s why I like you lol

    Tip: Not sure if you will, but I think you really should add pics like “Do’s and Don’t’s” to show examples of both right and wrong ways to dress, and how clothes should fit, just as you described. This is, after all, a chapter on appearance. It gots to be visual 😉

    Keep up the good Work Rami. 😀

    • Will definitely see about adding the do and don’t pics to that chapter! It’s a great idea. Attitude, personality, and hygiene are definitely dealbreakers when it comes to the ladies. Funnily enough, it goes both ways: it’s just that women seem to know they need to be clean and smell nice, whereas guys can be completely clueless about that really basic stuff 😀

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