Men’s Fashion rule #1 – Style

I don’t know about you guys, but until a few years ago I didn’t have a clear framework to work with for selecting fashion styles and clothes, and the “results” were clearly showing.

I was still dressing better than most, since the overwhelming majority of guys just don’t care about what they wear in the slightest, but still, I was not gaining any extra points on fashion alone, especially in my late twenties, when I momentarily lost direction in life, and you could see that also by the rock-bottom status of my wardrobe. Roughly speaking, I went through four different fashion periods before fixing things once and for all.

Between age 17 and 19, I was going after branded items of clothing, meaning that I was wearing clothes with evident-but-not-big brand signs on them, either the more casual line of high-end brands (e.g. D&G, Emporio Armani, etc.) or the “cool” brands of the moment. Think about Bikkembergs shoes, flashy deep V-neck T-shirts, lousy jeans with extremely low waist so as to show part of the boxer shorts underneath, “cool” belt with the “cool” brand written on it, Louis Vuitton pink men’s cap with little coloured flowers printed on it, you get the idea. Possibly there is a name to describe such a style, but it evades me. My girlfriend of the time was an extremely sought-after girl, who was dressing just like me, and actually she was the one influencing my fashion style. Thinking back at her behaviour and her attitude, she’s exactly the kind of girl I would quickly screen out right now.

Then, at around 20, I switched style of all a sudden, since I was feeling more serious and more “mature” inside, and I started to dress accordingly. This is when I started hunting for outlet stores, since the clothes I was going after were fairly expensive: if before I had in my wardrobe a few items by D&G, Emporio Armani and the like, now those items had been replaced with their Dolce & Gabbana and Armani Le Collezioni equivalents. I was wearing slim-fit jeans, slim-fit chinos, fitted shirts, fitted jackets, and I also got myself a fitted black coat. I was extremely comfortable in this new sharp fashion style of mine, since it matched with how I was feeling inside. The fact that the university city I was living in was much more casual and much more alternative compared to my new way of dressing didn’t bother me in the slightest, also because my very best friend of that period plus a few acquittances of ours were all going for fairly similar fashion styles, and we were often going to bars and clubs where people were aligned with our way of dressing (and thinking).

Roughly at 22, I made yet another natural fashion change, meaning that my fashion style was following how I was feeling inside. I started to take life way less seriously (while still working hard to get top university grades though), I was having a lot of fun even just with the little things of life, and my new clothes were following this new mindset of mine. I started going for much more casual and playful-asshole clothes, and I grow a little stubble as well. I have very fond memories of that time, since the end of the university is like a magic period: very hard work, but at the same time excitement for future opportunities and future job success (suuure), and most importantly, unawareness of the mediocrity and hypocrisy which was typical of the soon-to-be-discovered Corporate Land.

Starting from 25, shit hit the fan fashion-wise, since I got distracted by my new corporate life and a few personal objectives of mine. It didn’t help that I had just moved to a country which isn’t exactly renowned worldwide for its everyday fashion, and despite my wardrobe was quickly spiralling downwards, I still managed to be better dressed than most, both at work and when I went out. For my free time I was buying boring Nice Guy clothes, think of straight jeans, and at some point I even started going out with the New Balance 373, just to give you an idea of what we are talking about. My work attire was top-notch though, with slim-fit wool suit trousers, fitted shirts, and dress shoes. From 27 to 30 my wardrobe was simply a disaster, and it reflected the cringeworthy period I was mentally going through after losing direction and motivation in life. Then, and as we saw in a different post already, I made that disaster end at age 30, taking back control of my life and of my happiness.

Problem was though, I had decided to do something to fix my fashion (good), but at the same time I didn’t really know where to start (bad). And to this day, I’m extremely grateful to have discovered Darius’s “Sexy Style for Joe” website through (Links). Darius’s work focuses on helping men develop sexy fashion styles, the sort of styles which give you a head start in terms of generating attraction, and here are the five styles he recommends, with links to each of his relevant Pinterest board:


Keeping in mind that Darius’s website and Pinterest channel are our benchmark for men’s fashion, I also just created a channel so that I could embed a few relevant pins in here, just to give you a better idea of what we are talking about.


This is my favourite style of all, since it gets the balance just right IMO, not too formal but still on-point, and as sexy as it gets while still looking masculine (this is essential). It’s easier to pull this off in spring and autumn, since a leather jacket can do wonders here, but even a coat can work well with the right accessories and complementary items of clothes to go with it. Here’s the belt chain and separate key I bought myself.


It comes with a field-tested tease included to it.

Why are you wearing a belt chain?

With serious playful expression:

It’s to make sure I don’t lose an important key.

Oh…and what key is that?

With a serious silly expression and your eyebrows a bit up, as if you are about to tell a big secret:

Actually, …

Then with playful teasing expression:

…it’s the key to my chastity belt!!


Other teases are possible, considering that the key has the shape of a heart at the top, but I’ve not used any of them, since they would set a different and less sexual frame.


We are deep into “bad boy” style here, and even if I like it, I don’t use it very often. I tend to include at least one item that moves me to either the Elegant-Edgy or Smart-Casual style. Let’s consider the look on the left-hand side above: all other items of clothes being equal, if you wear boots you fall into this Edgy style, if you wear shiny black Chelsea boots you move to Elegant-Edgy, and if you opt for some more casual trainers you move to Smart-Casual. My go-to option in that case would be the Chelsea boots, similarly to the look in the left-hand side of the Elegant-Edgy pictures above.


This style is good, but I don’t use it at all, mainly because I think it wouldn’t fare very well in combination with my “angelic” face. Fact is, the balance between different traits is good, but if you try to balance two drastically different things with each other, then than the balance doesn’t work anymore. And also, this style is too “rugged” for my liking, I prefer Elegant-Edgy and Smart-Casual.


This is the style I use the most for everyday purposes, since it’s just more comfortable and easier to pull off compared the others. But I still like Elegant-Edgy more, since comfort and easiness of execution come at a price, and I think this style doesn’t give that extra boost we are looking for, even when perfectly executed.

At summer this is the go-to fashion choice though, since the two- or three-layer arrangements go out of the window when the temperature rises.


To me this style works for an evening date or to go to work, and I use it occasionally in winter, when the time is right to use my fitted coats. I personally don’t feel very comfortable with this style, since it’s too formal for my current liking, but YMMV. And also, I don’t know if it’s the same where you live, but here in Europe, where extremely casual things like the white Adidas Stan Smith have taken over, and most girls just don’t put any effort in dressing a bit better than usual, well over here this style is an overkill most of the time. It still works great in the right contexts and environments, this is for sure. And nothing beats a man with this style perfectly executed and at the same time not a hint of try-hardness in his expression, but problem is, those contexts and environments are getting extinguished.

Considering all that, if I go out at spring with a formal jacket, I make sure to balance that item with something that brings me back to the Elegant-Edgy style.


We have seen five different styles which can deliver a big boost your Looks. Fashion is something I recommend everyone takes seriously, since it’s where you can have the quickest returns on the effort you put in, together with grooming. Getting those two things right did wonders for me, and I’m sure it can do wonders for you as well.

Feel free to head over to Darius’s website and Pinterest channel (Links) to continue this conversation on fashion, and to have some more ideas on the different styles. There is a lot of research for you to do, both in terms of identifying the looks to replicate, and then to buy the relevant clothes matching your requirements in terms of style, fit, colour, fabrics, price. But as a relevant bonus, the winter sales are approaching quickly.

Related Posts:
• Maximising your Looks
• Men’s Fashion rule #2 – Fit
• Men’s Fashion rule #3 – Fabrics
• Glasses and Sunglasses: common mistakes

The Essentials:
• Fundamentals