A good baseball cap is deserving of a spot in any man’s summer wardrobe. But how should you wear it? In this week’s edition of Ask MR PORTER, we address the vital question of hat angles and what they say about you.

If you’ve got a style query that needs answering, don’t hesitate to share it with us at asky@mrporter.com.

We take a freewheeling approach to personal style at MR PORTER. Generally speaking, we’re of the opinion that if it feels good, you should do it. Having said that, we do urge a degree of circumspection when it comes to hats.

The thing about hats is that you wear them on your head, which makes them highly conspicuous items of clothing. There is simply no avoiding a poorly chosen hat; if it doesn’t look right on you, people are going to notice.

Just ask Amazon founder Mr Jeff Bezos, who took part this week in the maiden human voyage of his privately funded space tourism firm, Blue Origin, while wearing a taupe-coloured cowboy hat so ridiculous that it became more of a news story than the space flight itself – and, yes, that’s before we get to the shape of the spacecraft.

It’s important to note here that it wasn’t the actual hat that was ridiculous, but the fact that it was perched atop the head of the world’s richest man. The cowboy hat represents rootsy, working-class Americana; Bezos is about as far removed from the working class as it’s possible to get. The two simply do not mix.

And it’s this sense of incongruity that brings us to the issue in hand. An older man wearing a baseball cap backwards might not evoke quite the same reaction as the spectacle of Bezos’ billionaire space cowboy, but both situations ultimately boil down to the same question: can I pull this off? To answer it properly, a little historical context is required.

The backwards cap was first worn on the baseball field by catchers, to keep the brim out of the way of their protective masks. But it caught on as a cultural phenomenon following Mr Sylvester Stallone’s 1987 arm-wrestling movie Over The Top, followed by high-profile baseball star Mr Ken Griffey Jr in the 1990s. It owes its youthful, rebellious connotations to Mr Will Smith in The Fresh Prince Of Bel-Air, and, through the decade, musicians such as Mr Tupac Shakur, Jay-Z and, ultimately, Limp Bizkit’s Mr Fred Durst.

More intrepid style mavericks, such as Public Enemy’s Flavor Flav, took the trend one step further by wearing their baseball cap at a jaunty 90 degrees. However, this look has latterly become associated with early-career Mr Justin Bieber, and as such is not recommended for older guys.

That was then, but what about today? The rebel image of the backwards baseball cap has undoubtedly softened in recent years, attracting clean-cut sports stars such as Mr Tom Brady, who wore one on the Tampa Bay Buccaneers’ Super Bowl victory parade at the age of 43.

It still has its detractors, who argue that wearing a baseball cap backwards defeats the point of wearing one at all – no comment from us on that one. But at this point in fashion history, it’s hard to deny its mainstream status.

This newfound acceptance, combined with the ongoing cultural fascination for all things 1990s, might explain why you’re seeing so many men rocking the backwards cap at the moment. But can you pull it off?

While there’s nothing stopping you from wearing a baseball cap backwards at any age, what it really comes down to is self-belief. With any item of clothing, but with hats in particular, a lack of confidence will betray you. If you step out of the house thinking that you look like a man in the grip of a midlife crisis, there’s a good chance that others will come to the same conclusion.

If you think you’ve got the swagger to give it a try, what about style advice? We’d recommend trying a snapback cap over a fitted cap – the latter still has echoes of Bieber and Durst – and opting for a sporty brand, such as Polo Ralph Lauren or Nike, to underline the look’s sporting origins. On the subject of styling, it should go without saying that the backwards cap is an informal look suited to relaxed occasions, so put the rest of your outfit together accordingly.

And if you conclude that it’s a step too far? Thankfully, there are plenty of alternatives. Bucket hats are popular right now for similar, 1990s-related reasons, and have the benefit of looking the same whichever angle you wear them at. Stüssy and Carhartt are two of the archetypal brands, but there are high-fashion offerings from Fendi and Gucci, or outdoor-inspired ones from And Wander and Nanamica.

Or, failing that, you could just slip on your trusty old cowboy hat.