“But you’re not gay, right?”

I genuinely laughed, those cute freshman girls had no idea who they were dealing with.


Then one of them reached for my cardigan to close the bottom button, which of course was met by my not so subtle “unless afterwards you plan on opening my belt, I’d leave the cardigan’s button open”, said with a sly smile.

Despite the fun nature of this exchange, it had me on alert – it was the second time I was asked if I was gay that evening and even though the first interaction was even more amusing after a woman from our group, whom I’ve slept with, jumped in to answer that question with a “definitely, very not gay! I can vouch for that!” it still meant that something in my look is not right.

More specifically, I made three epic mistakes when dressing for a night out and despite my outfit being very stylish (even more than usual), it was sending the wrong message and creating the wrong image.

Few weeks ago I prepared an article on how to create your own “I’m getting laid tonight look”, one that WILL make you look hot, if executed to a point.

Today, I would like to expand on that piece and share 5 biggest mistakes you can make when doing that.

In this article I’ll assume that you’re no longer a complete beginner and have a basic understanding on how clothes should fit you and how to wear and coordinate colors. If that’s something you’re still not comfortable with make sure to check the following articles before moving forward (really, it won’t matter how well planned your outfit is if you haven’t mastered the basics yet.)


Tell me, when you go out do you feel like the hottest action in town and notice women regularly checking you out?

If not, read on because you’re likely making at least one of the 5 epic mistakes.

1. Not dressing for your body type

I’m sure dear ladies will agree – wearing ill-fitting baggy clothes when you have a great physique should be a considered a crime against humanity

If I could name a single mistake that seem to persist with stylish men more than any other, it would be not dressing for your body type. Even men who are otherwise well-dressed and know their stuff seem to forget their natural features:

  • Short men choose clothes and styles that make them look even shorter.
  • Tall men pick clothes that make their upper and lower body look disproportionate.
  • Skinny guys go for styles that seem to hang on their frame and make them look like stick-figures with a bag on.
  • While bigger fellows seem to have fetish-like fondness for clothes that even further emphasize their love for beer and junk food.
  • And fit guys just say screw this and dress in a way that hides their muscle and makes the look sloppy.

Knowing your body type and how to dress to make the most out of it should be your first focused effort after the basics are handled.

How To Prevent It:

Be brutally honest with yourself about your physique, facial features, grooming. I know it might feel more comfortable in the moment to ignore some of our less than awesome features (we all have those), but this way you’re not using clothes to their full potential – looking taller, thinner, more muscular, proportionate are all doable when using clothes in a smart way.

2. Not dressing for the venue

This was the first mistake I made on that particular night. Our first spot was an old school rocker bar with amazing beer and the average age of the crowd over 40. The second spot was an indie-style college bar.

I was overdressed for both venues, my elegant bad boy look (with an extra emphasize on “elegant” and not enough on “bad”) would’ve worked like magic in a sort of cocktail bar where people do try-hard a little when going out, but here I was simply sticking out and not in a good way.

How To Prevent It:

Be smart about where you plan on spending the evening and what you will be doing there. Ideally, you want to dress a bit better than most men in the venue, while still looking like you belong and “get it”.

This is the difference between looking like “the hot guy” and “is he lost?”

Don’t copy what others are wearing, but instead try to embody the vibe of the venue, event – if it’s loud and indie, go for edgy-casual looks, if it’s classy and dressy go for something more elegant (just don’t forget sex appeal), etc.

This brings me to the next epic mistake.

3. Dressing Way Too Conservative

I think I’ve snoozed just looking at the outfit.

Would you like to guess why business-casual (semi-classy) looks are the most popular among men, who are just starting out on the path of finding their style – it’s because it’s by far the easiest look to pull off when you want to appear well-dressed. That, and they tend to convey a little bit of status, which for many men, who are not aware of dressing sexy, is the Holy Grail of looking attractive, desirable.

It’s usually a manifestation of a desperate need to please everyone and god forbid someone will look at them funny or take offence. Unsurprisingly it’s also a highway to looking boring and pretty much asexual (at least you can buy her a drink.)

If you don’t notice any (or very few) glances from people chances are high that you’re playing it too safe.

How To Prevent It:

Unless you’re going to a formal event, with a dress code and all that, even your classier outfits should have some edge to it – this is what creates the sex appeal.

Add a bolder color, interesting accessory, cooler shoes, show some skin – all are very valid ways of getting rid of that stench that is “looking boring”.

4. Following trends religiously

It always makes me cringe when I see several guys wearing nearly identical clothes in the venue (often accompanied with nearly identical grooming). It gets almost comical when you see 3-4 guys like that standing next to each other.

Unfortunately, it is an indication of a pervasive issue we have with mass-produced fashion – few brands decide what they want to push that season and then nearly every other store provides a slightly altered variation of that same style.

Oh shit, I think there was a glitch in the matrix

Then, because most men don’t bother to educate themselves and instead just copy what everyone else is doing (usually the guy in his group that gets slightly more attention from women/is more confident) and because selection is so similar they end up looking pretty much the same.

In turn they all get placed in the same category of “the other guys” – sad, right?

How To Prevent It:

Knowing general trends can be helpful and there’s nothing wrong with buying clothes from mass-producing brands – I buy most of my clothes there too – instead, when it comes to standing out from the crowd of grey, faceless mass you need to develop your own sense of style, one that is tailored for your unique situation.

Avoiding the first three mistakes will take you a long way there, but you also need to be willing to experiment, try different things, when looking for inspiration on the internet instead of copying them blindly, understand why certain things work and which parts you could use for yourself.

If this this like a daunting task, I’ll be glad to offer you my help.

5. Dressing Too Masculine / Feminine

This was my second mistake during that evening: with a scarf, cardigan, scoop neck, Chelsea boots, slightly shiny black jeans and everything being nearly skin tight I was overwhelmingly dressing too feminine. It looked good, but it was lacking any dominance, threat it was just too “pretty”.

Oh, I’m sorry, I think I forgot my sex appeal in my other jacket.

The other side of the story, and one more commonly made by your average Joe, is avoiding feminine pieces altogether and dressing fully in practical, masculine pieces (puffy waterproof / windproof jackets and Timberland boots). The result, of course, is quite macho, but it also ends up having as much sex appeal as a carburetor.

How To Prevent It:

Even though ideally you want to stay on the masculine side with your outfits, a sexy look needs both feminine and masculine pieces. Keep this mind when building your look.

This means that, first and foremost, you need to get over your animosity towards feminine items like V-necks, scarfs, etc. Not only they are THE “good looking” items, but also in contrast they will make any masculine pieces you wear even more impressive and effective.

Evaluate your looks, notice on which side of the spectrum you’re falling and how heavily. Swap appropriate pieces to lean just slightly towards a masculine image and thank me later, when women start telling you how hot you look.

Bonus. Trying Too Hard

Unless you’re going to a gentlemen’s rave party – DON’T.

This was my last mistake with that evening’s outfit.

I will say this, getting attention, being complimented and noticing how you’re being checked out by beautiful women is very addictive. But like with every addiction, when you don’t get your “dose” long enough you start making irrational decisions just to get your fix.

In my case, I wanted to look impressive to a point where I forgot where I was going and what I was going to do there. This happened because I had a busy week, where most of my “going out” was to the gym and the grocery store and I have to admit that by the time it was Friday I got a bit needy.

How To Prevent It:

Like with most neediness related issues, abundance is the key and ideally you don’t want to go extended periods of time without meeting new people (women) or spending time with those you care about.

On a more practical note, make looking good part of your identity, self-perception. This way even your day-to-day errands will lead to plenty of exchanges that will solidify your knowledge that you’re an attractive man.

For example, yesterday I was shopping for a new fiction book to read before sleep. It was almost funny to notice how women in the bookstore where fishing for glances while I was browsing books in the FANTASY section and when our eyes meet with few of them, it was always followed by flirty smile. Life’s good.

This way, by the time you go out, you’ll be able to enjoy all the positive attention from women without getting attached, over-invested.

Lastly, all your outfits should have a sort of breeze, casualness and the aura of “it just happened” about them.

Finishing Thoughts (And Important Announcement)

I would like to anticipate and address one question – “is being asked whether you’re gay is really a bad thing?”

And the answer is no, not at all, actually most often when women ask something like this is because being sexual with you already crossed her mind. But generally it should happen infrequently and if it happens more than once during the night, chances are very high something in your look or your demeanor is not right.

Now, that’s it for today’s article, however, I would like your attention for just one more minute to make an important announcement:

This will be my last published article for at least several weeks (maybe a month). With the next one being an announcement for my first book being published. Here’s the deal, I have the book nearly ready sitting in my laptop for longer than I would like to admit, but finishing and making it worthy of your time and focus was something I’ve been procrastinating on and delaying.

By making this statement and making it official I will have no choice but stop distracting myself and get it done.

During this time, I will still continue to work with you personally and I will stay active in our inner circle group – working with you guys directly is still my top priority.