When I was in fifth grade my dad bought me my first pair of suede Chelsea boots. Of course I didn’t have a clue what Chelsea boots were back in those days so I just called them “cowboy boots”, which in my mind made them even cooler.

The fact that my father owned a similar pair made me even more excited, because even at that young age I knew that he had a pretty good eye for clothes – looking back at the repressive era he grew up in I must say this makes it quite impressive and you’ll soon understand why.


The first day I wore them to school I was very excited – surely all my guy friends will think they are awesome and will be jealous.

First class was gym class and I would meet all of them in the locker room.

My childish excitement was shattered almost immediately after I enter the locker room:

“Hahaha, Darius, why are you wearing girly shoes?”

I was mocked… A lot… Because of my shoes…

In the following classes I had girls from our class tell me that they thought my shoes looked really cool and all that but it no longer mattered – guys, who’s approval I was unconsciously seeking deemed them “girly” and I was feeling like an outcast from our group because I stood out.

I don’t think I wore those shoes ever since…

Even worse, this event made such an impact on me emotionally that I actively started avoiding clothes that would make me stand out in any way. So I started copying people who had absolutely no sense of style (your typical teenage boy) and by the time I hit high school my eye for good looking clothes was utterly useless and in turn I got very little attention from girls.

It was a long and expensive (so many clothes bought that were completely unwearable) road to get to a point where I feel comfortable and confident in my eye for clothes and style again.

By the way, if you find yourself thinking that Chelsea boots are girly and refuse to experiment with them just because of that – congratulations, you have fashion sense of a fifth grader (hmmm… potential new TV Show – “Are You More Stylish Than A Fifth Grader?” haha)

But don’t worry, hopefully by the end of this article, you’ll be back on track to developing your own eye for good looking clothes.

How Social Pressure Forms Our Views Towards Clothes

We all like to think that we’re special individuals with unique points of view, but the truth is we’re very much the result of our upbringing, environment and social influences we accept into our lives.

There’s a quote by Jim Rohn: “You are the average of the five people you spend most time with.” And I think its spot on. It also very much applies to how you dress and present yourself:

  • If you mostly hang out with metalheads or a similar crowd chances are you’ll be wearing a lot of black and your clothes in general will be on the edgier side. Chances are you’ll also be growing out goofy facial hair that you think looks badass.
  • If you hang out with preppy crowd you’ll likely think that polo shirts are sexy, cool and shorts are a good-looking piece of clothing for warmer weather.
  • If all of your friends are hipsters you probably find yourself thinking that super skinny cuts are too loose.
  • And on the other hand, if your friends are all wearing baggy cargo shorts and think they look badass, you’ll probably find yourself thinking that anyone who is wearing slim cut jeans and has their hair longer than buzz-cut is a “hipster jesus”.

But this goes well beyond just people you hang out with. Few more factors come into play:

  • The type of music you’re listening too – chances are you’re consciously or unconsciously copying your favorite performers.
  • The type of hobbies you have – if, for example, you’re an avid MMA fan chances you own a few Affliction t-shirts (or similar designs).
  • Where you live – what you think is good style will be very different if you live in a small town in a middle of nowhere than if you live in a metropolitan fashion capital.
  • The TV shows you’re watching and characters you like – when TV show “Californication” was in its peak every other guy in the seduction community started copying Hank Moody’s (played by David Duchovny) look, thinking it’s a sexy look because a fictional character seemed to have a lot of success with women (I hope I don’t need to point out the obvious logical fallacy here).
  • Your upbringing – what your father, older brothers, sisters, people you hang out with are wearing, will make a lasting influence on what you think are good looking clothes.

The question then is – which social influences are correct, which of them are helping you dress sexier, look more attractive and which are holding you back, making you blind to the fact the clothes you think are cool are actually ugly-as-fuck and generally shouldn’t be worn outside certain, thematic events.

How To Know If Social Influences In Your Life Are Helping Or Hurting You?

Here’s the deal – there’s no one correct answer, that’s why during personal style consultation I cannot just stamp same outfits to everyone based on their physique and facial features or why we already have few dozen Style Inspirations here on SSfJ and will have even more as time goes.

Context matters A LOT and different looks will work best in different situations. For example last weekend I spent in a metal music festival – it’s an extreme situation where super-edgy/intimidating outfits are deemed the most attractive and even my edgier combinations that would get not-so-friendly glances anywhere outside that setting was mellow and “nice guy-ish” in comparison.

Still, there are a few things we can do to get a better understanding whether a particular social influence in our life is helping or hurting us when it comes to looking sexy.

First, the basics, and most importantly fit – I don’t care if you’re in an indie bar, metal festival or in a corporate office – fit is universal and a great indicator if a particular influence in your life knows that it’s doing when it comes to style.

If you notice that someone you’re copying are wearing oversized, baggy clothes that don’t really fit them chances are high you need to re-evaluate whether you should continue looking up to that group/person for style advice.

Secondly, ask these questions for yourself:

  1. Is the motive for a particular outfit is to maximize sex appeal or something else?

Let’s take few examples:

  • In most cases the goal of metal bands with their image is not to maximize sex appeal, but to create an intimidating, dominant effect. Other music genres focus on different characteristics they want to convey “rebellious attitude” (punk), “chill, casual, laidback” (reggae), etc. Actually very few music genres / artist focus on maximizing sex appeal directly, which is why think that modeling band/artist looks is not always a good idea unless you’re heavily into the scene and are into women who also spent a lot of time in that scene.
  • Most sport celebrities get a huge bag of money to wear brand names. So you need to ask yourself, are they wearing those sneakers, tee shirts, hoodies because they like them or because they are being paid a shit-ton of money to do so in public. Brands known for a long time that most people will copy celebrities blindly and invest a lot of money into this type of promotion.
  • TV shows often focus on making their main male characters relatable and generally dress them down to match lowest common denominator – your average Joe, who has no idea about style. Even when they don’t (Matt Bomer in “White Collar”, Neil Patrick Harris in “How I Met Your Mother”) they are usually presented in a very dressy way because it’s easier to sell as sexy to those who never learned about dressing to maximize sex appeal and attractiveness.
  • Most men’s style sites focus on making you look respectable, professional, well-dressed, which is great if you’re going on a business lunch or a job interview but their goal is not to make you look as sexy and attractive as possible, which is why they might not always be the best influence to learn how to dress for dates and meeting women.

That’s not to say that modeling your style based on celebrities, TV show characters, etc. is always bad – not at all, there are a lot of very stylish famous men, and being well-dressed and respectable is NOT mutually exclusive with looking sexy but we need to be smart about it and critically think why do we think something looks good or not.

  1. Your peers – are they getting the result you want and are they getting it because they dress sexy or despite their style?

This is a bit tricky, because it’s very easy to fall for an obvious logical fallacy, but bare with me.

Think about people you hang out with the most, they are obviously influencing how you see style and clothes – now tell me, are they getting the results you want?

  • Are they regularly complimented by women how hot they look?
  • Are they getting plenty and then some?
  • Do you notice women checking them out when they enter a venue?

If you can say yes to all three questions, there’s hope. Still as I’m sure you know it’s possible to be considered hot and good looking without actually dressing to look attractive – maybe they have a great physique, male model looks, high social status or simply are charming and charismatic to the point where how they dress stop mattering that much.

Let’s take the good old David Duchovny playing Hank Moody in “Californication” – many guys copy his look because they think his character is attractive because of his very simple, casual outfit but the truth is writers gave that character personality and charm that would make him attractive to many women even if he wore a stained, oversized t-shirt.

Unfortunately, most of us here don’t have this benefit of having an extremely attractive personality scripted for us and in turn to get best results when meeting women, we could use the extra edge that comes with dressing sexy.

So here it is,

Try to critically think when you’re modeling your friends and peers who you know are successful with women whether their style is playing for them or against them, because “he wears sleeveless t-shirts + he gets laid = therefore, sleeveless t-shirts are hot!” is not good reasoning.

  1. When modeling looks you see online, the outfits that clothing brands promote – do they look good because they are displayed on very attractive male models or because the outfits themselves are attractive?

In “Nerdy To Sexy” in the chapter on modeling I talk about how clothing brands are great at promoting their clothes by using very attractive male models to create an illusion that if you wear those clothes you’ll look just as hot.

Unfortunately, the reality is not quite so rainbows and unicorns – most of those outfits would actually look quite shitty on a regular guy, who’s still paying his dues in the gym and has an average face.

So when looking for outfits to copy online think about this – how it would look on your not-so-attractive male friends (imagining them on ourselves can be a bit tricky and it’s easy to fool ourselves). I usually use one of my chubbier programmer buddies for this and you know what, most of those outfits SUCK!

Ignorance Is Bliss, But It’s Also The Reason Why You’re Not Dressing Sexy

The unfortunate reality is that when you start on this path you don’t really know what actually looks good and which clothes look bad/don’t suit you.

Over the years you develop a sort of taste based on feedback you’ve been getting:

  • “When I wear this shirt guys don’t say any negative comments, few guys even said it was cool.”
  • “When I wore those shoes that one girl even said they looked nice.”
  • “My mom picked me these pants and told me they look good on me.”

And unconsciously over the years we form our initial taste in clothes. But as we discussed earlier not all of those influences were actually trustworthy and possibly the clothes you think look cool now are actually quite “meh…”

So you start learning about style, go shopping for new clothes, you look for clothes and try to guess if they are actually stylish and good looking or not.

“Well, this tee has some interesting graphic on it. It’s kind of funny, I guess. It’s also by a cool brand that I saw those famous skaters wear and with an appropriate, sizeable price tag so it must be cool…”


Unsurprisingly, back in the day, in the forums that focused on helping men get better with women no one even bothered with giving style advice and instead told guys “just take a female friend/gay guy friend shopping with you and let them pick the clothes for you.

This was obviously a better option than simply guessing which clothes look good and suit you, but it has quite a few drawbacks too (but that’s a topic for another day.)

Those, who had bad influences when it comes to men’s style but still persisted to get better, like myself, often spent a ton of money on clothes that were ugly only to realize in a few weeks that those purchases were pretty much unwearable.

In my case, I never had a lot of money to spend of clothes, so every bad purchase was very painful.


What’s worse than that is that many men never even bothered to question their influences and don’t eunderstand how underdeveloped their eye for style (especially dressing sexy) is.

They don’t understand how much they are missing out by being adamant about their personal style “well, that’s just my style and those are the clothes I like wearing.

How To Know If Your Eye For Sexy Clothes Needs To Be Re-Calibrated

So now, what are the tells that your eye for good looking clothes needs to be improved and that you might be missing out right now on compliments and attention from women.

The first tell is quite obvious and yet probably the most important one:

How often women compliment you on your style or particular pieces of clothing

Assuming you’re not reeking of desperation and don’t look like you’re baiting compliments, women love commenting and complimenting on clothes, especially shoes and accessories. So if you rarely, if ever, get positive comments on your outfits, chances are you’re doing something wrong.

When you do it right, you should regularly notice women (not all women, not always) checking you out, stealing glances – a stylish, sexy man is a rare and valuable commodity!

Are your tastes go heavily against current men’s fashion?

Open a site like Pinterest.com, write “men’s style” into the search bar and go through the results (ignore all the suited up guys and infographics) or better yet, go to our Pinterest page and compare what you wear on a daily basis and when meeting women with what you see there.

If what you’re currently wearing is way off from what you see, chances are you still have places where to improve your dressing sexy skills. There some nuances like heavily niche looks that work great in a certain context but overall finding similar looks to yours is a great indicator that you’re doing at least something right.

Do you know why are you choosing particular clothes?

I’m not the artsy type (nothing wrong with being one) as I always found math and physics easier and more enjoyable than art classes and with this mathematical precision I try to approach men’s style.

When you know what you’re doing, clothes and style becomes less of a gut-feeling guesswork and more of a science – you know what to look for, you know what visual effects certain clothes and details create and you know what character qualities they add to your overall image.

If you’re choosing your clothes mostly unconsciously and out of a habit, chances are you have quite a few pieces in your wardrobe that don’t look flattering on you or shouldn’t be worn in the first place.

Exceptions to this is if you have a natural talent for clothes or had a lot good influences in your life that helped you develop an eye for style.

Okay, I probably scared you enough to start throwing clothes out that you’re not sure about or write me something along the lines of “Daaaarriuuuss!!! Help, does this t-shirt looks good?! I have a date in two hours!!!”

So it’s time to discuss how we can develop our eye for good looking, sexy clothes.

Developing Your Eye For Sexy Clothes

Depending on your starting point, developing your eye for good looking clothes can be a slow process but its definitely achievable by most (maybe even everyone) and there is a process to it.


Critically question the influences (peers, environment, people you look up to) that form your attitude towards clothes

Are you modeling your tastes based on stylish people, who know what they are doing, or like myself back in school days, you’re trying to appease your social circle, where most people are actually are quite clueless about clothes and style.

Replace bad influences with new, good ones that in the long run will help you dress sexy

Being aware that certain influences might not be great for you and are taking you in the wrong direction will be very helpful but it won’t do much if you don’t consciously decide to stop seeking style guidance from them.

And even if you do, it won’t last if you don’t replace those bad influences with new, good ones – like bad habits those influences need to be replaced with good habits.

Men’s style sites, /r/malefashionadvice (reddit), Pinterest, Instagram, Youtube all has great resources, people to follow and advice to take from.

And of course, SexyStyleforJoe is here for you! (Especially our Style Inspiration series)

When you’re first starting out, you will likely feel resistance:

“That’s not me”

“I could never wear that”

“Come on, this can’t look good, can it?”

“This looks so complicated”

“This would never work here”

But it’s simply years of bad conditioning and influences talking. Sure, not everything will work in all cases, but you need to find courage to experiment, take those first steps or you’ll always stay that “random t-shirts, ill-fitting jeans and ugly sneakers guy.”

Find someone to help you out

I was very fortunate, when I first started out on developing my eye good looking clothes: I had a female friend, who studied fashion design to take with me shopping.

Having her tell me what looks good, what goes well with what made all the difference in the world. When I would shop for clothes with her and later wore those outfits to classes, I would always stand out in the best way possible (though looking back, it’s not difficult to stand out when you’re studying computer science and most guys are utterly clueless about clothes).

On the other hand, all my bad, unwearable purchases happened when I went out shopping alone and didn’t have someone experienced to consult.


If you know anyone in your life who’s obviously stylish, well-dressed (be it male or female) ask for help, take them out shopping for clothes with you. They should push you to try out things (you don’t necessarily need to buy them) that you would never dare on your own.


I’m always looking for guys to work with and personally help them out.

Notice stylish, attractive men and try to consciously deconstruct what they are wearing, which pieces of clothing stand out in a good way

I’m not exactly sure where I first found this technique, it might be the old Kinowear site (back in the day when Jay ran it), but it’s definetely one of the best strategies to speed up the process of developing your eye for style and good looking clothes.

The idea is simple – you notice stylish, well-dressed, sexy men and consciously focus and try to deconstruct what in their outfit actually makes them look so damn good.

At first you can do it with photos online (men’s style sites, pinterest pages, etc.), then you can do it with your peers (assuming you have stylish men in your group) and at a certain point you’ll get comfortable and efficient at it to the point where you can do it almost instantly when you pass such men in the street.

In your mind you should be able to answer these questions:

  • Which pieces of clothing are the main attraction points? What do you think would get complimented by women?
  • Why this outfit works well? (Fit, colors, specific items)
  • What you could change, maybe even improve?

Learn what to look for in clothes

As mentioned earlier, there’s a method to all this madness that we call men’s style and even though there are exceptions, there are “best practices” on what to look for/avoid in specific clothes.

For example, you definitely don’t want any graphic designs on a polo shirt; jeans and trousers can have distressing and other details but you don’t want more pockets around thighs or below; etc.

This is why a big part of the book in “Nerdy To Sexy” is dedicated to discuss exactly that – what to look for and avoid in specific types of clothes.

Don’t shy away from standing out and experiment with new stuff

When you’re very young and don’t have a strong identity you desperately want to fit it so standing out can be daunting. Still, at a certain point you need to stop seeking approval and trying to please everyone, otherwise the only thing your style will say about you is “just another dude”.

Push yourself to try new things, even if it’s just in the changing room, you’ll be surprised what actually ends up looking great on you.

Make it a habit to challenge your assumptions and try bolder items.

Personally, to this day I constantly change my style and experiment with new stuff to see what’s working and what’s not (well, it’s kind of my job now anyway.)

Finishing Thoughts

When working with guys personally I always find items in their wardrobe that are unattractive and are holding them back. Even though I can’t work with all of you personally (and I’m sure not all of you would want that in the first place), with this article I hopefully gave you enough to think about and strategies to apply to do a “style intervention” and get rid of those ugly-ass clothes and replace them with something that will make you look sexier.



(Photo credits: bobbi vie)