Styling a jacket involves so much more than merely throwing it on over a shirt and heading out the door in a rush. Sure, that’s the go-to on those dramatically frantic mornings that find you reaching for the keys with one hand and your coffee with the other. But when there’s time, making a few adjustments to your men’s outerwear styling techniques can make a huge difference in the look you convey throughout the season. In reality, the options are almost endless—yes, even if you don’t usually put a great deal of thought into the type of jacket you wear or how you wear it.
The 1980s would have been proud. Think of this as the modified version of a look that’s typically best reserved for the Marty McFlys of the world. If you own enough pairs of men’s jeans to outfit a small country, then you have no reason not to make this happen. First, a nod to the functionality and endurance of the enduring jean jacket: It’s been around for centuries, and it’s a brilliant example of a hard-working, foolproof garment that has near-universal appeal. The key is to avoid pairing it with matching jeans, as this may look too much like a haphazard suit and less like an effortless yet stylish outfit. Instead, pair that classic jacket with something a little more tailored, like a pair of corduroy pants or chinos. Colors like tan, brown, and gray are best, as these create some balance without pulling away from the understated nature of the entire outfit. Since denim is highly casual by nature, lean in that direction as you step into your shoes, too. Suede and canvas sneakers are always safe choices, as are chukka and motorcycle boots.
In keeping with the “by the decades” theme, it seems only fitting to add a 1990s-inspired windbreaker to your cold-weather arsenal, too. The ubiquitous topper is a dream when you’re dealing with classic autumn weather, whether it’s a sudden storm or heavy wind gusts that chill you to the bone. The beauty of a windbreaker is that it falls into many categories: It’s timeless, sporty, and classy all at once. You can lean fully into the look and pair it with joggers or jeans and a pair of sneakers if you want to keep things low key. If you’re wearing a windbreaker jacket in a neutral color like tan or black, however, think outside the confines of casual dress. First, look for a silhouette that’s not too loose or breezy but more fitted to your form, much like a shirt might be. You should be able to layer something over that, like a light sweater. Then add a jacket along with something more reserved, like tailored men’s pants and a pair of sleek loafers. Top it all off with a lightweight sweater in an opposing color underneath to add a surprising pop to the ensemble.
The bomber jacket has always been the epitome of cool. The iconic topper is a military mainstay, of course, but it also has a revered place in modern-day popular culture. The likes of Tom Cruise, Brad Pitt, and David Beckham have all sported theirs at various times and places of great import: movie sets, red carpets, fashion shows, and film premieres, to name but a few. The bomber is almost absurdly versatile, largely because it’s available in so many iterations. There are lightweight styles best suited to breezy spring days, and heavier options filled with down and edged with fur collars. How you style it depends largely on where you’re headed. Your errand run may be a relatively casual affair, for example, but you can pull your look together by throwing on your bomber over matching bottoms and adding a contrasting men’s polo shirt or tee underneath. Or take it in an old-school direction by zipping it up over a contrasting shirt and finishing with a pair of tailored slacks and loafers, sans socks. The effect is straight out of the 1950s.
There’s a certain grace involved with long overcoats and jackets that are layered over slim pants and smart tops. The look is undeniably polished, and certainly more pulled together than the average casual ensemble. What does it take to achieve this look? One key factor: confidence. To pull off a long jacket of any kind, whether it’s a sharply tailored topper or a more substantial parka, takes some extra effort. That’s mainly because you need to establish a balance from top to bottom to avoid overwhelming your look. On a cooler day, throw that long jacket on over a men’s cashmere sweater, a pair of straight cut jeans, and sturdy boots that match the jacket. If you’re wearing something thicker, like a wool overcoat, throw that on with smartly tailored pants, glossy dress boots, a button-down shirt, and a scarf to achieve a quintessential “downtown chic” look.
If you’ve long fantasized about living in another era, you can at least look the part in a varsity jacket. Boasting all of the cachet of an Ivy League institution, the classic topper is a little more versatile than its counterparts because it’s more casual. The beauty of the grown-up version is that it’s also timeless—you don’t need to worry about retiring it at the end of the football season. Keep color choice at the forefront of your mind: Neutrals are best, as they pair well with everything from jeans to slacks. Think of the varsity jacket as a hyper-charged addition to your sportswear collection. It’s cool and effortless, yet decidedly more hip than the usual jacket you grab before you head out the door. You can take an extra-sporty approach with canvas sneakers and joggers, or keep it more reserved by wearing it with tailored trousers for a more vintage-inspired appearance.
The jacket is definitely more versatile than you may realize. It pays to invest in various styles that play well with different facets of your wardrobe, whether it’s lightly breezy or downright cold.