Men’s Leather Jackets Style Guide

How can the humble leather jacket, a single item of outerwear, manage to demand such a wide range of reactions? Think about it for a moment. Rugged masculinity, sexy femininity, edge, classic conservatism, daring, aggression, rebellion, and chic unreachability – there are Leather jackets that suit almost any style, any attitude, and any expression. But only if it’s the right jacket. The right person. The right package. So which is right for you, and how can you avoid investing in a defining piece or fashion that just gives… the wrong definition? Let’s start with a quick survey of the general styles on offer.

This was probably the first style to hit the market that looks anything like what we think of as a modern leather jacket (`cause let’s face it, the cavemen were sporting leather outerwear to impress the cave women a long time before we came along). There were developed to be warm and hard-wearing, suitable for pilots in the early days of unheated, rattling, bone-jarring flight. This style suggests reliability, a connection with the past and strength of character. It is generally available in light or dark browns, black, and occasionally dark grey. This isn’t a style that gets played with much – it is a solid, unchanging staple. If this jacket suits your sense of style and matches the message you want to send out there, then let it do the work. The clothing you wear under it should be understated, classic, and not fight for attention with the jacket itself. Remember, this style is all about suggesting what’s on the inside. Tradition. Character. It doesn’t need dressing up.

This variation on the flight jacket is designed to be a bit more streamlined, a bit more modern in its appeal. It is a lighter option, opting out of the sheepskin collar and liner, going instead for a straight zip, low-profile collar, and pockets that are visible, but not shouting out for attention. Unlike the flight jacket, bomber jackets are often seen in more vivid colours, from Eddie Murphy’s red or purple versions (complete with matching trousers), to the cool style of Steve McQueen. Tan versions might suit the creative tech executive, black might give an edge to an otherwise soft and playful look, and dark purple with studs, safety pins and a bit of graffiti… you get the idea.

Another early entry into the leather jacket categories was the biker jacket. Made for Harley Davidson motorcycles, and heavily inspired by the flight jackets that just preceded them, biker jackets are made to look cool, but have design features that are very functional too. The zippers are asymmetrical, so a biker can lean forward without the zipper digging into the soft skin of the belly. There is a pocket high on the chest, usually at a stylish angle, for keys or wallets, as the early leather riding trousers were tight, stiff, and not well-suited to keeping things in the pockets. These jackets are meant to look tough – but they aren’t able to do so on their own. I’ve seen trends of wearing these jackets with polo shirts and kakis, but I don’t recommend it. To my eye, it doesn’t fit the look, and can come off a bit try-too-hard, or fake-tough. If you’re going to pull off a jacket like this – even if you yourself don’t look like a tough-guy – you can do it by keeping the clothing under it as classic and cool as the jacket itself. A pair of well-worn jeans. A t-shirt. Leather boots or understated trainers. Steer clear of bright colours, or anything – ANYTHING – you might see included on a ‘smart-casual’ dress code.

Now we’re moving into a different era of the leather jacket, but we’re not quite there. The field jacket sits in the gap between the rough-and-rugged needs of pilots and rebel bikers and the more elegant, socialite settings of high society. These are the jackets of the Victorian aristocratic explorers, men who had personal libraries, but would rather be out finding Mayan ruins with a strong of deerhounds at their heels. Think Dr Livingstone, or even Indiana Jones. Characterised by multiple pockets, protective flaps, high collars and longer lengths, these jackets are more difficult to wear well, because the rest of the outfit needs to be reflective of the balance between rugged and refined. Go back to that ‘smart-casual’ list for these supporting garments. Chinos, white trousers, a new pair of jll not be published.