These are the tools: you have to use them

Monday, April 5th 2021
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“Can I wear dark-brown shoes like these with a suit in my office? Do you think it would be appropriate?”

The answer is, I don’t know. I don’t work in your office: I don’t know what the implicit dress code is. You have to make up your own mind.

I can explain why things are more formal or less formal. I can show how things of a similar formality - or style, or tradition - go together. But you have to judge the context. You have to decide what’s appropriate. 

Essentially, websites and books can give you the tools, but you have to use them. 

Actually, more than that: only by using them yourself can you develop your own sense of style.

In recent weeks a few Indian readers (going by their names) have been asking about some of the fundamentals of dressing smartly: what shoes go with what trousers, how to dress smarter without wearing a suit. 

They are clearly learning from scratch and are admirably curious and self-aware. But there comes a point where I can’t answer their questions. When they have to take the tools they’ve been given and apply them to their culture and context. 

I think this theme - of learning from others and then from your own experience - is an interesting one, because it doesn’t just apply to guys starting from scratch. 

Even when you’ve been dressing well for a while, and consistently look both appropriate and flattered by what you wear, you might not quite have developed your own style. 

This personal style is often what makes people great dressers. But it requires both a knowledge of the basics - which may have been consciously learned or subconsciously absorbed - and then consistent play and experimentation.

Returning, first, to those readers just starting out. 

One wanted to know about trousers: why suit trousers are often too smart, sharp and smooth to wear with casual jackets. 

They might learn the answer by reading about tailoring cloths, and the difference between worsteds and woollens. Or, they might learn the principles that smooth, sharp, dark, plain materials are smarter than coarse, loose, bright, patterned ones. 

Either way, once learned these things should become intuitive. So that when they look in the mirror at an outfit, they know the trousers look wrong with the jacket, and that they need to be swapped for something more casual. Those principles they initially read about have become instinctive, involuntary. 

It’s easy to scoff at people that learn this way. Those that do scoff, however, are obeying the same principles. The only difference is how they learned them.

It might have been from their parents, who simply showed what looked good every day. Or it might have been from talking to their peers: girls do this intensively, I find, and a lot more than boys.

If you had none of this early education, you need to learn it more explicitly. And reading it in an article is a lot quicker than years of osmosis. 

When you do learn like this, it can take a little encouragement to apply the ideas yourself. 

Another of those readers, for example, asked about the social situation in bars he went to. Everyone else wore shirts and trousers or jeans. No one wore a jacket or tie. Would he stand out if he did? 

I assume so, yes. Certainly I can’t tell him from all the way over here.

But if he’d like to dress better without standing too much, I can give him some tools. For example, understanding the sliding scale from structured blazer, to soft-shouldered jacket, to completely unstructured, to overshirt. 

Each is more casual than the last, and he can pick where he wants to be on that scale. 

Another tool would be understanding which colours look smarter than others. Or why an overshirt with epaulettes, bellows pockets and a pleated back draws more attention than one without. 

Now let’s jump forward in time, to the more experienced dresser.

Last week I got talking to a reader who lives locally. He’s been a fan of the blog for years, bought clothes in most areas we’ve talked about, and built up a nice, quality wardrobe. 

He was wearing an old, belted Belstaff jacket in a size bigger than I would have worn. He was wearing a denim shirt and jeans in pretty much the same shade. He was wearing trainers in fluorescent colors. 

But he looked great. And as we chatted about the pieces, what he liked about them, it occurred to both of us how he had built on those early principles over the years. 

He understood good fit, and knew the advantages and disadvantages of the oversized jacket. It had an slouchiness to it that he liked, but he controlled it by keeping the belt cinched. 

He knew very well that double denim was more risky, more of a ‘look’. But he had chosen that to be more unusual, to be more playful. He did it quite often.

The trainers were certainly bright, but they were fairly slim too - Nike Daybreaks, I believe, in yellow and turquoise. Their silhouette fit in very well with everything else, even if the colours stood out. 

And he’d done it all instinctively - not spelled out as it is here, but quite simply and naturally, because he simply understands clothes.

I only wish he’d allowed me to take a photograph of him. 

Clothing can be helpfully thought of as a language. Some people absorb it when they’re young; others have to learn it when they’re older. 

Whatever the method, the more you learn, the more you can express yourself. And that’s the journey most people are on with clothing. I certainly am. 

I very much look forward to those new readers growing in confidence with their clothing, and starting to wield these tools (to switch metaphors) themselves. 

I hope they continue to read, comment, and help others that are just starting out too. 

Clothes pictured:

For more on the 'rules' and how to understand them before breaking them, see the Guide here.