It’s a really important question to address, “how high can I go?’ – at work, with mates etc. Get it right and you will never ever have any problems with adding height. And it is all about lifestyle and different situations in your life, as well as your existing height. I have spent over 15 years wrestling with this and even now I learn new things about it.

The first point I have to make is that no doubt in an ideal world you would like to jump straight into 5” elevators (“hell, why don’t they do 6” – or MORE?!”). You wanna be as tall as possible.

But practical considerations dictate that in some situations if you actually go that height, you sacrifice some other aspect of style…and the overall look is then wrong.

There are different aspects of this and one of them relates to the other clothes you wear – every day, at night, casually, on weekends. These are really important.

The most common of these potential problems is, for example, when wearing a suit or formal pants/ trousers. Suits pretty much always demand a certain type of shoe (or modern boot style), however fashionable. By and large, great clumpy boots and obvious thick soled shoes look all wrong. And with heavy boots plus a suit, there is a danger that it LOOKS like you are adding height, which is the opposite of what you want to achieve. The material tends to hang wrong and the boots flash up at you.

I have a pair of Ischias (4”/10cm) and a pair of Shanghais 5”/12.5cm) – just look at them in the GuidoMaggi site: the Ischias are PERFECT for a suit because they are not thick soled and the suit material slips neatly over them as if they were a totally normal pair of brogues or wing-tips. My Shanghais are superb with jeans or in my leathers on the bike (and I love that extra inch of lift, oh boy). Now I would love to be able to gain 5” instead of 4” when I wear something like that suit. But I cannot, because unless that thick ‘Doc Martens + suit’ look is in style and other guys are all wearing it (and sometimes it is, hooray), it just seems all wrong. So go with the flow, accept it. It’s only an inch.

There are loads of examples like this, where what is fashionable (and more importantly what is not) dictates that you should be careful how much you add.

Sometimes fashion is right with you – in the UK, a decade ago when I really started adding serious height I was helped by the fact that very flared pants were in fashion. I wore the widest flares, real long inside leg, and then the most massive shoes packed with lifts etc. Today it would be elevators of the very highest!! But that trend is long gone and no way could I do it today! You have to start with your own style and build your height addition around it. You cannot just bolt on 5” thick-soled elevators to anything and everything. A pair of 4” or 3” ones will do just as well, and will look way easier in most mainstream stuff.

With jeans, there are a number of caveats – in the UK and Europe, skinny still rules. Most young lads wear them, but not all – and they vary in skinniness: some are skin tight and superstretch. With these, if you wanna wear very thick soled 5” boots you CAN but it is a specific style and takes a bit of finessing. I have done it and am never detected but I do occasionally worry about the style – it is very ‘in your face’ and focuses attention on the boots. This is not a problem with that style, as it is quite mainstream, specially in winter. But you have to be into that style.

In general, though, if you wanna go real tall, then stick to bootcut jeans (plenty of modern slim-ish styles) and I have found even better is to have frayed hem bottoms, even to slim cut jeans, and even sometimes a slight split in the seam again down at the base of the hem, so that the material drapes over the boot and particularly the back of the boot. I try to avoid the material bunching and riding up on the boot which can then make the heel area look chunky – you want the jeans, however slim, to sort of hang around or drape over the boot as long as possible and over the leather. A break in the hem WILL allow that and looks cool as well, specially if frayed.

Generally, the slimmer that width of the pant leg, the more careful you have to be about drawing attention to heavy shoes. If your style is for baggier stuff (and there are some – limited – signs that it might make a revival), well you are lucky…you can wear almost anything unless you turn the hems up heavily.

Next time I am going to focus on another area of ‘how high can I go?” and it relates to your ACTUAL current height. That is important and a factor is decinding how high you can go.