• Home  / 
  • Style
  •  /  How To Dress As A 40+ Man So Women Will Go Crazy Over You

How To Dress As A 40+ Man So Women Will Go Crazy Over You

how to dress

Below is an excerpt from my upcoming book on game for 40+ men. Here I discuss fashion, and some general principles that I observe when choosing clothes.


Although style in theory incorporates your overall ‘look’ I’m talking about fashion here and keeping this separate to grooming, which is about your hair, skin, beard and so on separate.

While my tastes have changed over the years, certain things for me have remained constant. Fundamentally I believe that when a man enters the room he should make an impact. This is absolutely not about ‘peacocking’ or any nonsense like that. This is about wearing decent, well-fitting clothes that ensure you will create a strong silhouette and command attention.

I wrote an article some time ago about men’s clothes and what they should wear in which I argued that two key elements should always be present. These were power and mystique.

Addressing the idea of power, I wrote the following:

Remember, game is all about communicating value, and what better value is there to display than power?

Now, before people get the idea that this is all about wearing Armani suits and Tag watches, remember that power can mean a variety of things. Yes, there is the power that comes with wealth and influence, either political or commercial. But there is also the muscular power of the male body. Or the creative power of the rock musician, or the sporting power of the pro-athlete.

Have a look at what you’re wearing now and ask yourself honestly whether it makes you look powerful in any way. If you’re wearing a baggy old polo shirt, some chinos and a pair of old sneakers then the answer is probably no. I’m not suggesting you have to jettison these for a blazer and pocket square, as that may not be your thing, but what you must do is ensure that your clothes tell people that you are a together individual who possesses power of some kind.

In other words this is not necessarily about wearing an Armani suit and an Hermes tie, but it is about ensuring that your clothes fit exceptionally well and that you achieve that sharp ‘silhouette’ I was referred to earlier.

I went on to say this about mystique:

Which leads on to the second point – never be generic. You should instead always try to ensure that your clothes look just a little bit different, just a little bit unique, to communicate a little mystique. This is different to the old concept of peacocking in that you shouldn’t allow it to take over your whole outfit. Instead, you should just add little splashes of colour or detail—such as a designer pocket square, or cufflinks, or an unconventionally-cut coat—that mark you out as an individual rather than a neck-bearded loon.

Women love a man who is hard to pin down. If you’re an open book then you are not creating enough attraction. So try to bear this in mind when you are choosing clothes and incorporate little touches that make her wonder about you.

This is notionally closer to the idea of old peacocking concept, although I try to avoid anything quite so crudely straightforward as that. Basically what I advocate—and the rule that I try to live by myself—is not to be generic.

What you seriously want to avoid is being a basic jeans-and-a-hoodie kind of guy. Not that there’s anything wrong with jeans, as long as they are well-fitting, and even a hoodie can look good if it’s teamed with a blazer or a smart jacket. But the point is that you don’t want to look like the kind of guy who just rolled off the couch after an afternoon watching the football.

Men’s wardrobes are of course composed of staple items that are common to all. So for example I have trousers, jeans, blazers, shirts and t-shirts in mine, as well as shoes and overcoats, and you probably do too. This is unavoidable, but what makes us stand out, and a trick that we can pull from the female handbook, is using accessories smartly to create a better outfit.

Examples of this vary, and some will be to your taste more than others. But I’m talking principally here about things like cufflinks, pocket handkerchiefs, ties, jewellry (rings, bracelets, neck chains etc). There are also those items that introduce a splash of colour like fancy socks, colourful trainers (i.e. Nikes) and even embroidered designer baseball caps.

There is also the trick of mixing up formal and casual notes. I have already mentioned wearing hoodies with blazers. Another option is the ever-popular jeans-with-a-blazer look. I am also still a big fan of wearing suits with a t-shirt instead of a shirt. If the t-shirt is black or white and the suit is dark then you can achieve a very impressive Italian-type look without breaking the bank. You might also opt to wear (clean and good quality) trainers with such an outfit, again blurring the smart-casual lines.

What you should always do, though, is to ensure that there is some element of surprise in your wardrobe. That you are not merely beige and vanilla, as so many other guys are.

How Much Should You Spend?

In terms of how much money you should spend, I have long been of the opinion that high street stores serve just as well as the designer labels for most basic outfits. I once heard it said, for example, that no t-shirt should cost more that $20 and I would still say that is a reasonable rule of thumb. I have owned designer clothing in my time as well as that from low-cost stores like H&M, Zara and Primark (although Zara rubs up against high end these days) and they’ve lasted me for years, while some of my designer items have looked tarnished and old after a season.

My expenditure on clothes therefore breaks down something like this. I don’t spend much at all on t-shirts or underwear. I will spend more on shirts, as they have to be well-fitting and well-made, and not crease too easily. I will also spend a bit more on jeans, as they need to be quite hard-wearing. I will spend proportionately more on suits and blazers, as these must be well-designed and well-cut to look good. I will also spend more on shoes, again because they need to be hard-wearing and to last, and on coats, because in the winter I tend to be wearing my coat a lot and so it is the key thing that people will see.

Indeed, if you look at that summary you will see that in general the things that are most visible to others are the items that you should invest more in. So for example I would spend proportionately more on a coat than I would on trousers because, frankly, more people are likely to notice the coat. At the moment I have a very nice coat from Reiss which is made of pure wool and has a furry black collar. It cost several hundred pounds, but I wear it with t-shirts and a black snood from Primark because, well, no one is able to tell. Plus the obvious quality of the coat gives the illusion that the other things I am wearing are of a similar standard.

As with game and business, when it comes to style perception is more important than reality.

For a collection of my best writing on game from the last five years, get a copy of How To Get Hot Girls Into Bed on Amazon

For exclusive additional free content every week join my subscribers list here. 

For daily updates follow me on Twitter

About the author