How to Level Up Your Wardrobe: A Primer on First Impressions


Today’s post might be one of the more important articles we’ve ever posted on Nerd Fitness.  Last week’s article on body image was incredibly well received, and today we’re going to take a look at the stuff we wear OVER our bodies, something I ignored for far too long but didn’t know where to find help.  A few years back, I met Barron of through the blogosphere and we have become good friends since then.

Last fall I decided it was time to level up other parts of my life and stop dressing like a mismatched college kid.  So I emailed Barron: “Here’s a small budget.  Can you help me not dress like an idiot?”  He helped me pick out a few key items, and almost overnight, I was transformed…into a sharply dressed idiot!  

Because I had started taking pride in my appearance, I felt better about myself and thus exuded more confidence.  I immediately noticed a change in how I was treated: from the stranger at the airport counter, to the cashier at the grocery store, to the cute girl at the coffee shop.  Seriously, I couldn’t believe how my clothing changed how I felt about myself and how others perceived me.

At a conference this past summer, with lots of friends who only see me once a year, I couldn’t go more than five minutes without getting complimented on my appearance.  My physique honestly hadn’t changed much – it was just that I finally started wearing the right kind of clothes for my body type!

I figure I can’t be the only one who is clueless, but didn’t know where to turn or how to get started.  I can help you level up your life; Barron is going to help you level up your armor.

Note: this article is mostly beneficial for the guys in the audience, though quite a bit will be applicable to ladies as well.  Sometimes we’ll have articles that are more beneficial for guys (like this one), while others we have published (like this and this) will be more helpful to women.  We’ll end up doing a similar article helping out ladies soon!

Take it away Barron.

Your body is a complicated tool, an intricate system.  The moment you are mindful of its well-being, changes start to occur.

If you’ve committed to improving your body, whether you’re already a modern-day Leonidas or simply a work in progress, today I invite you to also level up the way you present yourself.

After all, why work hard leveling up everything else in your system, only to neglect the very last and easiest upgrade: your clothes.

Think of it this way: In every role-playing game you spend time leveling up, gaining skills, spells, and new attacks to defeat your enemies. But you also have to suit up with armor, either for protection, to enhance your overall strength, or to simply strike fear into the hearts of your enemies.

Today we’re going to learn how to treat your clothing the same way!

Suit up let your clothes enhance your already awesome self, helping you put your best foot forward in completing the quest at hand.

Why you should level up your wardrobe

colorful wardrobe

You’re in full control.

In your life, there are many circumstances that may be out of your control, but the way you present yourself is not. Even if you aren’t at your ideal bodyweight or you’d still like to lose a few inches from your waist, you can still pick out something to wear that will make you look and feel great RIGHT NOW. We’ll go over exactly how to do that in a little bit.

Self-confidence reflects as much inward as it does outward.

If you’re not confident and self-assured inside, you certainly won’t seem it on the outside. Same goes for if you’re uncomfortable (or in some cases, too comfortable) with what you wear in your day to day life. If you’re schlubby and unkempt, there’s a good chance that lack of care is reflecting what’s going on inside.

When Steve asked me to help level up his look in preparation for his upcoming talks, he was already an engaging speaker with plenty of experiences to share.

He knew looking the part could only help him. The better his armor, the more confident he’d feel in his task to nail the talk.

Steve learned, by visually asserting himself by appearing put together and polished, he immediately sent unspoken signals to people. As a result he received an unprecedented number of compliments on how good he looked and how confident and strong his message was.

It’s crazy, but true. The way you present yourself drastically affects how people perceive you and the things you have to say.

Whether you like it or not, you’re judged by your appearance.

Your face and your clothing are the first things people see. You may be dedicated to your health, eating clean and regularly setting that squat PR. But at the end of the day, the clothes you wear, your superhero attire, will be what people see first.

You may be thinking, “I don’t care what people think,” and that’s fine. Just keep in mind that first impressions are powerful. The way you present yourself says a lot about you, as well as how YOU feel about those who come in contact with you.

You’re here, you’re a Nerd Fitness reader. You DO care!

It’s not too late to upgrade your armor

iron man

I went to Catholic school as a kid, and even though we wore uniforms most of the time, I always remember caring about my personal style. My friends and I enjoyed “free dress days” when we could come to school in our regular clothing and express our individuality.

If there’s one thing us nerds have in common, it’s standing out from the crowd.

…though maybe we just wanted to show off our cool new T-shirts we bought with our allowance money. If your transformative years happened in the early- to mid-90s, you must remember these prints.

Growing up, I established pretty terrible eating habits, which only became worse as I got older. Eventually, my never-ending appetite caught up with me, and in my third year of college, I topped off at 241 lbs. Funny enough, despite my size, I always received compliments about how I dressed. From time to time, I was even asked for advice by my close guy friends, which eventually inspired my now four-year-old site, Effortless Gent.

Around my senior year in college, something clicked, and I realized I needed to change. Over the next two years I lost over 80 lbs. I look at old pictures from just a few years back, and I hardly even recognize that guy.

But the one thing that has stayed constant was my interest in dressing well, even through the highs and lows of my transformation. I always saw it as a way to express myself, even though I felt totally insecure and out of control when it came to my health and fitness.

What is the point of all this endless rambling and back story, you may wonder?

For one, it’s never too late to upgrade your armor and have it work for you, not against you. It’s never too late to start caring about your appearance and how you present yourself.

And two, despite your background, situation, or size, a little effort with your presentation can help you get the reactions, confidence, and respect you deserve.

Misconceptions for not caring

lego wardrobe
Your armor may be a simple surface-level addition, but what it stands for is much more than that.

It’s how you choose to represent yourself…a display of your pride and your self-esteem.  

It says you care enough to make a good first impression, that you’re knowledgeable, well put-together, confident and self-assertive.

Steve’s anecdote shows us that your look can create self-esteem, not just project it. Dressing well gives you a certain presence that sloppy dress does not.

Just try it out once, and observe the reactions you receive from others. Don’t be surprised if you get a bunch of positive comments, or more than a few lingering glances from others. Keep in mind that dressing well doesn’t always equate to dressing up. It’s all about dressing well relative to your everyday lifestyle and situation.

Here are a few common excuses I hear and why they’re totally unfounded:

“I don’t know where to start!”

Similar to creating new habits for change in both your diet and exercise, start small. Choose one thing, work at it, and soon enough, it will just be your normal outfit, routine, or way of life. The simpler the change, the easier it is to keep.

This may mean improving just one aspect of your presentation. For example, focus on one great work outfit, and not your whole freakin’ closet (which can be overwhelming, I know).

“It’s too hard and I don’t know what I’m doing.”

If you follow the Lean Wardrobe philosophy, you’ll realize it’s not as difficult as you think. It’s all about owning a few simple basics—items that are all interchangeable—which minimizes the need to think. Easy peasy!

“I live by myself / play video games in a basement all day / work in a cubicle, no one cares what I look like.”

Studies suggest that your presentation affects how others perceive you as much as how you perceive yourself. Crazy, right? Start to dress differently and begin to feel differently as well. And in turn, people will start perceiving and treating you differently.

I work from home and I know for a fact my day is much more productive and focused when I put on something work-appropriate, instead of shuffling around in the shorts and T-shirt I wore to bed the night before.

“I don’t want to appear vain / shallow / self-absorbed.”

Is building muscle vain? What about losing 100 lbs? How about deadlifting two times your body weight? How shallow is that? Leveling up your life is about becoming the best version of you, whether it’s about your style, self-esteem, max deadlift, or LOTR knowledge.

Four big takeaways

bow tie

Every person’s situation is different, so instead of giving you absolute “You should…” statements, I’ll leave you with a few thoughts and big takeaways apply to both males and females and are totally actionable right this second.

Understand how clothes should fit.

Fit is of utmost importance when it comes to your clothing. If you’ve never given it a second thought beyond how comfortable or uncomfortable a certain article of clothing is, there’s a good chance your clothes are either WAY too big or WAY too tight on your body.

The importance of fit in dressing well is akin to the importance of form when weightlifting. You must master fit for your specific body type before you can begin to replace your whole wardrobe. Just like you must perfect your form before increasing the weight on the barbell.

Recognize your body’s proportions and let your clothing create illusion.

Think of clothing as a tool to re-draw your body’s lines, thus creating these illusions I speak of. You’re basically Criss Angel-ing your body! But, you know, in a more useful and less freakish way.

When clothes fit you properly, they seem to re-draw lines and help you look in proportion and balanced… and everyone wants to look balanced, right?

Here are some examples:

  • If you’re a big guy, your first inclination may be to purchase a size XXL when you’re actually an L, thinking the extra room hides your size. In actuality, massive clothing just makes you look bigger. Trust me, I’ve made the same mistake before, when I was 80 lbs heavier. Buy your size if you don’t want to look larger than you are.
  • If you have long legs and a short torso, you can appear more proportioned and hide that imbalance by wearing pants that rest below your waist, closer to your hips.
  • Ladies, if you have a wider midsection or are more pear-shaped (narrower in your torso, wider in your hips), you can balance this by wearing clothing that accentuates your natural waist—the slimmest part of your torso—with the rest of the garment flowing away from your body.If you’re shorter, try V-neck dresses and tops. This visually elongates you, making you appear taller. For a shorter, pear-shaped body: add visual interest to the waist, wear a long neckline to elongate, and find a garment that flows from your hips, like this. 
  • If you’re very tall and/or skinny, break up your height by utilizing things that cut you in pieces, visually of course. That means a substantial leather belt for your pants (you’re tucking in your shirt, right?), and cuffs in your jeans. You can also wear bolder prints (like your favorite plaid shirt), but avoid bold vertical stripes, because that will just accentuate your height.
  • If you’re built smaller, shorter, or more petite than most, it would help to avoid patterns and lines that break up your height. Smaller scale patterns and textures also help. If you’re shopping for a suit, it’s a good idea to find a shorter jacket with a lower button positioning, which will aid in your efforts to appear more proportioned, and thus taller.Consider the size of your accessories. Stick with smaller watches and rings, skinnier ties, etc., which may look miniature on a guy that’s 6’5″, but perfectly proportioned for someone who’s 5’6″.

See what I mean? View clothing as yet another tool in your arsenal when looking to put your best foot forward.

Use color to your advantage.


The colors you choose to wear make a big difference in how you look overall. It’s different for everyone because we all have different skin tones, but here are two tips:

1.) Don’t wash yourself out. Clothes in solid colors that are close to your own skin tone aren’t a good idea. It makes you appear pale and washed out, like you’re wearing a flesh-colored skin suit. Just check out the difference a bit of color makes to the guy in the T-shirt above. Same guy, three different T-shirts.

2.) Focus on contrast. Contrast is key. Contrast between your clothes and your skin tone. Contrast between your top and your bottom. Contrast is more visually appealing, generally speaking. Wearing clothes too close in tone to one another (as in, green pants with a green shirt and green shoes) doesn’t look very good unless done right. And I don’t have to explain why contrast between your clothing and your skin tone is a good thing. Just take a look at T-shirt guy one more time, and compare first two photos to the third.

Keep that wardrobe lean!  

Just like Steve advocates for a basic workout plan with big compound movements, I advocate a Lean Wardrobe because it’s the easiest way to stay organized and look great with minimal effort and money. By definition, a Lean Wardrobe is the minimum number of items you need to create a flexible, well-rounded wardrobe that suits your daily life. For Steve, we picked up a nicer pair (but still inexpensive) pair of jeans, well-fitting shirts (slim fitting J-Crew shirts are his new go-to), two ties, and a pair of nice dress shoes.

The whole point is to assemble a collection of items that work well with each other. You do this by choosing classic items in simple colors.

Key words: Simple. Classic. Clothing that won’t make you cringe when you see photos of yourself in twenty years.

Man to man, just tell me what to wear! 

shirt wardobe

[Steve’s note: I asked Barron to include this section for any guys like me, in need of SPECIFIC instruction.  I honestly felt clueless and wanted Barron to just tell me what to buy.  If that sounds like you, you’re welcome!]

Some rebels may thrive off general, overarching principles, enjoying the journey of experimentation and coming to your own conclusions…while others may want specific items to place in your inventory.

For the gentlemen, here’s the perfect starter kit. Add to this three-piece set at your own risk, and do so wisely, and after the appropriate amount of research so you’re not wasting time or money. Even if you just stick with these three things, you’ll be better off than 95% of your peers.

The Bare Minimum: Three-Piece Starter Kit:

1) One pair of straight-leg dark blue denim

Make sure this is dark dark blue, like midnight. Almost black. You want this to look raw and unwashed. No fake distressing, no embellishments, no studs, no cutesy patterns on your butt pockets.

Why dark blue? This style of denim is perfect for all situations. You can wear it with a T-shirt to your buddy’s house or on a date with a dress shirt.

Why straight-leg? There are plenty of variations, as far as fit is concerned. A simple straight-leg pair is classic and will never go out of style. You may need to try different styles if you’re huskier / skinnier than the average guy, but just go with what is most comfortable.

Here’s some further reading on the right denim. 

2) One white and/or light blue casual shirt

A simple, casual, white or light blue shirt will look great anywhere you go. Wear it with your dark denim and you can’t go wrong. That could be your go-to “more dressy than normal” uniform.

Make sure you find one that fits your body well. “Slim” is the key word (yes, even if you’re a bigger dude). Too big and billowy and you risk looking as out of place as Seinfeld in his unforgettable Puffy Pirate Shirt.

Here’s some further reading on the right casual shirt.

3) A decent pair of brown leather “dress” shoes

I put the word “dress” in quotes because if you’re not used to them, you may think they’re strictly for “dressing up.” But trust me, they can (and should) also be worn casually. Again, I’m giving you extremely versatile options, so you don’t have to spend too much time thinking, buying stuff, or worrying about how to put it all together.

Get the right pair and you can wear them with your denim, khakis, even that oddly-fitting suit your mom bought you in middle school (I’m advising against this, but technically, you could).

Why brown? The dark brown leather color looks great with the things I mentioned above. It’s dressy enough for that important meeting your boss is making you attend, while at the same time, casual enough to be worn with the dark denim you picked up.

Why leather? It all comes down to utility, and using things in the environment for which they were made. Sneakers, Vibrams, and flip flops, for example, were all made with a certain purpose in mind. Wear them when you’re performing the activity they were meant for. For regular, everyday situations, wear a decent pair of leather shoes.

Here’s some further reading on the right pair of brown shoes.

Think of these three things as bare essential gear in any game: the basic armor and weapon that you need to get started. Just pick up these three things and you can get right into battle. Don’t worry about getting other accessories until you have these basics.

Keep it simple and get started 

james bond lego

You care about leveling up your life, cleaning up your eating habits, and becoming more fit through exercise, otherwise you wouldn’t be reading Nerd Fitness. If you take the time to improve these aspects of your life, care enough to take that one final step to present yourself in the best possible light.

If you improve your self-presentation, the way people perceive you and the way you perceive yourself will change dramatically.

Just know the basics. There are a few style “rules” you’ll need to understand when you’re starting from the very beginning, but once you get the hang of those, it’s pretty much a free-for-all. Personal style is just that, personal, and you can interpret that to mean whatever you’d like.

When I first decided to do something about my ballooning waistline, I changed what I ate and I hopped on an elliptical machine. I didn’t know anything about macros, eating paleo, or strength training. All I knew was that I had to do something.

Treat your journey to style self-improvement the same way. Learn one thing, act upon it, master it, and move on from there.

Create simple daily habits that support these improvements, and let them become natural to you. Accept that it won’t be easy, but it will be worth it, and just do your best.

If you have questions, need advice, or simply a word or two of encouragement, I invite you to reach out directly or hop on over to the Effortless Gent community, where you’ll find a bunch of guys who can either lend a hand, or are on the same path as you.

What sort of questions do you have?   Have you changed how you dressed and noticed a change in how people treat you?


Barron Cuadro runs Effortless Gent, a site dedicated to helping guys figure out their personal style and what looks best on them. For those you like me (in need of some serious help), check out his Guide to Dressing Like a Grownup.


photo source: skin tone comparison, iron man, shirt wardrobe, lego wardrobe, bond, colorful wardrobe, marvel

The Last Fitness Program You’ll Ever Need

Workouts, nutrition guidance, and habit-building. Never wonder where you should put your limited time, energy, and effort.

Get our FREE Starter Kit with dozens of resources today!

This field is for validation purposes and should be left unchanged.